March 1st: I paid for Claude CoWork. Goal: do more while expending less energy. And eventually bring that leverage to my marketing team and outbound sales motion.

It didn’t go well.

The first thing I wanted to automate was sending iMessages. Keeping up with people over text, even the ones who matter most to me, feels weirdly draining. I avoid it. Feel bad about it. And wanted to fix that. But the Claude CoWork iMessage integration didn’t work for me, so I walked away.

I used Claude to draft some blog posts and make some PowerPoint decks, but didn’t get any further with automating my life.

Till today.

April 22nd 5PM: I sat down to try again. It’s currently 7:41. Everything below - including these 3 pretty cool workflows - all happened in the past 3 hours.

5PM: The Setup

I asked Claude to send an email to my wife. It’s first instinct was the native integration — connect Claude directly to Outlook. The “right” way.

But it hit a wall. An Outlook connector exists, but my company’s IT admin would need to first approve it.

So I zoomed out. RPA has been a thing for a decade. Can’t Claude can take control of my desktop? Perhaps it can go “over the top” and do whatever I need the same way I would.

I Gave Claude control of my computer instead.

It took 5 steps to get “computer use” working. Install the chrome extension, enable screen recording, enable accessibility settings, etc.

And then I tried again.

This time it opened the Outlook desktop app (didn’t even know I had that), waited a few minutes (because nobody had opened that app before), navigated to compose, filled in the recipient and body, and sent the email.

No API. No integration. Just Claude operating software like a person would.

I watched it happen in real time. Wasn’t sure whether to be impressed or slightly unsettled. Landed on impressed.

“Holy shit,” I thought. “I’d better take some screenshots. This could totally be a substack post.”

5:45PM: The Text Message Test to My Bestie

As I said, I find texting exhausting. and the native iMessage<>Claude integration hadn’t worked a month ago. So I tried the same workaround.

I told Claude who to text and what to say.

Claude pulled up iMessage, found the right conversation, typed the message, hit send.

The text it sent to my friend Rags:

Done. That’s the win. Not waiting for perfect integrations. Finding a path through anyway.

5:47PM Now We’re Cooking with Wispr Flow

I’d been hearing about WisprFlow — it’s voice dictation that lets you narrate instead of type. I’d set it up on my iPhone weeks ago, but hadn’t really seen the point.

But today I was inspired.

So while Claude was doing its thing, I installed WispFlow on my desktop.

Wispr says my voice runs 3x faster than my typing. Less friction going in, which means I actually stay in it long enough to get somewhere.

6:21PM: But Can It Talk to Microsoft Teams?

Next I decided to see if Claude could go “over the top” to send a Teams message to a a coworker. When I’d hit that Outlook integration wall earlier, I figured I should ping our IT guy.

Claude actually has a native Teams integration — but like Outlook, Jason would need to approve it.

Same workaround: Claude opened Teams, found the right conversation, typed the message, paused to get my approval, and then hit send on it’s own!

SUCCESS!

The irony isn’t lost on me that I used Claude to ask whether we’re allowed to use Claude.

The desktop workaround sidesteps the permission issue for now — but it’s a question every company is bound to be grappling with.

6:40PM: Drafting the Substack Post

I decided I wanted to try to publish my adventure. Tonight.

(BTW that never happens. most of my posts are months in the making)

So as we did the Teams message, I started narrating my journey via Wisprflow into Claude.

I asked Claude to make edits.

I asked Claude for Title and subtitle options.

And then I had Claude go into chrome, into Substack, find my publication, and paste the draft.

Holy Smokes. It did it! 🤯

7:24PM: Where This Is Going

Three Hours using Claude CoWork and I feel like a trailblazer.

I’m now editing the substack post and Claude is working on a social image to go with it.

So “What’s Next?” as my dear President Bartlett might say.

I’d love to automate a coordinated string of outbound sales touches — emails, LinkedIn messages, and SMS.

SMS especially.

When you’re selling to CEOs and leveraging personal relationships, a text is the most intimate and powerful channel. And thus far, it’s also been the channel with the fewest integrations into the standard sales automation tools, which means it’s reply-rate is still excellent. If Claude can drive that natively through the desktop, that could be a real edge for me and my team.

Final thought: WisprFlow as a Writing Tool

One last thing: this was the first substack post I’ve ever written entirely by talking, not typing. Every word was narrated into Wispr Flow into Claude.

I still did the final round of editing by-hand — that was the most time-consuming part - and I don’t know that i’ll ever allow the robots to take that away.

But they say it’s easier to edit than to write from a blank page. And the Wisprflow→Claude→Substack creative process was 100% a game-changer for getting past that blank page.

Paid Meta and Paid Google have been my top two growth drivers across 20 consulting clients, 5 CMO roles, and 6 exits. But something has fundamentally shifted in the last 18 months that most agency relationships haven’t caught up to. You’re probably still paying your agency for work that the Meta algorithm now does on autopilot — while chronically underinvesting in the two areas that actually move the needle.

I hate the phrase “let’s break it down,” so let’s… dig in, shall we?

The Old World (Quick Version)

Note: most of the argument below deals with Meta Ads, but at the end I’ll cover the way Google Ads is earlier-on in the same shift.

Paid Meta used to have three distinct layers, and each had real craft to it.

Layer 1 — Creative: static ads, video ads, landing pages. Important, but often treated as a separate line item or an afterthought.

Layer 2 — Media Buying (the expensive middle): targeting, bid strategy, audience testing, reporting. This was where agencies lived. A good media buyer could meaningfully outperform a bad one. Choosing the right demographic and interest stacks, building lookalike audiences, setting the right bid caps — this was an actual dark art. You’d pay $10-20K/month for it, and it was largely worth it.

Layer 3 — Data & Tech: passing conversion events, tracking setup. Most agencies punted on this entirely. They’d send you a list of pixels to install and call it a day.

That model made sense for a long time. It doesn’t anymore.

The Middle Got Hollowed Out

Here’s what’s happened: Meta’s algorithm has eaten the media buyer’s lunch.

Advantage+ audiences — Meta’s broad targeting product — now outperforms manual audience targeting in most scenarios. Meta benchmarks show Advantage+ delivering 7-15% lower cost per result versus detailed targeting, with some verticals seeing ROAS improvements of 20-35%. The algorithm is ingesting behavioral signals at a scale no human account manager can compete with.

And then there’s the regulatory layer. If you’re in finance, housing, education, or employment, Meta’s Special Ad Audience restrictions — stemming from HUD settlements around discriminatory targeting — mean you can’t target on age, gender, or detailed interests anyway. Age is locked to 18-65+. All genders must be included. Interest-based targeting is heavily restricted. In other words, you’re running broad targeting whether you like it or not.

The old skill of “choosing the right audience” has been commoditized and, in many cases, legislated away.

So what are you getting for that $15K/month retainer? Someone to watch dashboards and write a weekly report that largely recaps what you already saw in Ads Manager. That’s what.

Where the Value Has Actually Migrated

The juice has moved up and down. The middle is dead.

Up → Creative

Go look at the ads that brands were running five years ago. I’ll wait.

Painful, right? Text-heavy static images that looked like they were made in Microsoft Paint. Expensive, highly-produced brand videos that felt like repurposed TV commercials — because they were!! None of it felt native to Instagram feed. None of it felt authentic.

Now look at what the best-performing brands are running today. Dozens of UGC creators. Dozens of angles. Rapid-fire hook testing and reverse-hook testing. Raw, native-feeling content that blends into the feed before it punches you in the face with an offer. UGC-style video ads are outperforming traditional creative by 30-40% in CTR, and reducing CPA by 25-50% in many cases. The UGC production market literally grew 69% year-over-year from 2024 to 2025 — from $4.5B to $7.6B globally.

This is where the creative leverage is. Not in a pretty brand video. In volume, variety, and velocity.

Down → Data & Tech

This is the other layer agencies have historically ignored, and it’s now where some of the biggest performance gains live. The fundamental idea is that now that targeting is mostly-controlled by the algorithm, we need to feed the algorithm as many quality signals as possible.

A few tried-and-true levers that improve CAC:

• Server-side conversions (Conversions API / CAPI). If you’re still relying purely on client-side pixel tracking, you’re flying blind. iOS changes, browser restrictions, and cookie deprecation have made the browser pixel unreliable. Brands implementing CAPI report 15-20% improvement in campaign performance and a 44% increase in lead conversion rate versus standard lead ads. The reason: better signal quality going back to Meta’s optimization engine.

• Event match quality. It’s not just about sending the conversion event — it’s about how well Meta can match it back to a user. Event Match Quality (EMQ) scores of 8+ — achieved by sending enriched fields like hashed email, phone, zip code, state — can yield 20-40% higher conversion accuracy. Most brands are sitting at a 4 or 5 and leaving massive money on the table.

• Passing down-funnel signals. I see way too many agencies optimizing for the first step in the conversion funnel (i.e. Leads or Purchases). The real unlock is passing signals about which customers are actually good: LTV, subscription retention, deal size.

  This is a huge needle-mover for longer funnels: at Coding Dojo (coding bootcamp, helped 3x revenue and get acquired), one key unlock was switching Meta from optimizing for lead form submissions to optimizing for sales-call-meeting-show-ups. That was a lot more work. But it drove a double-digit improvement in CAC because it helped the algorithm focus on quality.

• LTV - You can pass total LTV for a user (not just the value of this purchase). And there are now a coterie of third-party tools that can pass a “predicted LTV” by enriching the user data. This helps Meta optimize toward your best customers, not just your most conversions.

• True down-funnel attribution outside the ad platform. Pulling campaign, ad set, and ad-level data through to your CRM, Data Warehouse, and BI tools so you can measure actual revenue, true LTV, and payback period — not just platform-reported ROAS. The ad platforms double-count (i.e. Google and Meta both take credit for the same conversion).

  The only solution is to have your own attribution data. And a good agency partner will help make sure you’re setting up Google Tag Manager, GA4, UTM parameters, and your CRM so that having your own attribution data is possible.

Your Renegotiation Playbook

Okay, so here’s where I’m going to give you the cheat sheet. If you’re renewing with your agency — or shopping for a new one — these are the specific terms to push on.

On Creative:

Strategy without execution is worthless. If your agency is currently charging you to develop a creative strategy brief but isn’t actually making the ads — cut that line item immediately. That’s just a Claude PowerPoint deck you’re paying for.

If they do have in-house UGC creative execution capabilities, push them to throw a meaningful amount of that into the base retainer. Don’t let it live as a $10K/month add-on.

If they won’t budge on that, consider a different mental model: freelance media buyer + UGC creative studio.

Get competitive quotes from dedicated UGC studios — there are good ones that’ll produce 10-15 pieces of content a month for $2-3K more than what you’re paying for that strategy deck.

On Tech & Data-Plumbing:

Here are some plays that will drive efficiency. If your agency hasn’t been owning these things — push back hard:

1. Setting up new events

2. CAPI (server-side conversions)

3. Passing more data like city, state, zip

4. improving event match rates

5. piping exclusion and retargeting audiences in directly from the CRM

6. Passing down-funnel data like meetings completed or LTV

7. Measuring CAC, ROAS, Paypack period down to the channel, campaign, and adset level

And expect them to own integrating ads with your CRM. If they’re 100% relying on in-platform data, they’re not doing their job.

So Do You Even Need an Agency?

The answer isn’t no. But the job description has completely changed.

The agencies that survive this shift aren’t media buying shops. They’re creative production studios with a strong data and measurement spine. If your current agency is primarily defined by its ability to manage Ads Manager — you are funding a dying agency. Like Blockbuster in 2007. You can see the writing on the wall if you squint.

What you want is an agency that can: (a) produce high volumes of native, UGC-style creative at speed, (b) own your measurement infrastructure end-to-end, and (c) use media buying not as the main event but as the operational layer that connects creative and data together.

Everything else is overhead.

P.S. — This Isn’t Just a Meta Problem

Everything I just described? It’s happening in Google Ads too.

Five years ago, keyword strategy was its own dark art. Exact match keywords, negative keyword lists, match type discipline — a good SEM manager could meaningfully outperform a mediocre one just by knowing how to structure a campaign. You paid for that expertise.

Today, Google is pushing everyone toward broad match + Smart Bidding, and the data increasingly backs them up. Broad match with a solid conversion signal now routinely outperforms tightly sculpted exact match structures. Google’s own internal studies show broad match driving 35% more conversions at a similar CPA when paired with Target CPA or Target ROAS bidding. Match type obsession has become a bit like debating seating arrangements on the Titanic.

And then there’s Performance Max. P-Max is Google’s version of Advantage+ — a fully automated campaign type that cuts across Search, Display, YouTube, Gmail, Maps, and Shopping simultaneously. The lever you actually control? The quality and variety of your creative. Sound familiar?

The agencies that used to differentiate on keyword architecture and bid management are facing the same existential question their Meta counterparts are. And the answer is the same: the value is in creative and in data. Everything else is getting automated out from under you.

Running paid Meta or Google for a client and want a second opinion on where your agency is actually creating value? Hit me up.

In this interview, Shaan Rupani, currently leading Growth at Knowde, formerly Head of Growth at NexHealth, and previously at Fair.com and Dropbox, shares how Fair.com transformed its customer acquisition model by building a fully automated, personalized ad system that slashed CAC by 90%. We discuss the strategy, execution, and lessons learned, as well as his broader thoughts on the emerging role of Growth Operations.

Growth marketing isn’t just about spending money efficiently—it’s about architecting systems that drive sustained, compounding success. Few people understand this better than Shaan.

Joining the conversation is Aditya Vempaty, currently VP of Marketing at MoEngage and a Mentor at First Round Capital, who brings his own perspective on the evolution of growth teams and operational efficiency.

Fair.com’s Growth Strategy: Automating Ads for Hyper-Personalization

Prasid: Let’s talk about Fair.com. What’s one specific marketing or growth initiative that really stood out?

Shaun: When I joined Fair.com, we were relying entirely on referrals, so our CAC was essentially $0. But once we needed to scale, we had to introduce paid acquisition. The conventional approach would have been to run generic ads across Google and Facebook, but we knew that wouldn’t be cost-effective. Instead, we developed an automated system that dynamically created thousands of personalized car ads in real-time, matching users with relevant inventory. This dropped our CAC by 90%.

Aditya: What was the conventional approach in the industry at the time, and how did your strategy differ?

Shaun: Think about an ad you see for something like Autotrader.com. The default playbook is generic ads about the platform and it’s benefits. For mobile apps the typical acquisition playbook was to focus on the benefits of the app, and run Google Universal App Campaigns and Facebook ads with generic creatives.

We flipped that by integrating our ad-buying systems with our live inventory data. Instead of serving generic “Get a car with Fair.com” ads, we dynamically built thousands of real-time ads showing actual cars available in the user’s area, with accurate pricing and direct deep links into the app. This level of specificity, relevance, and personalization had a massive impact on CTRs and CAC.

Prasid: Awesome. Let’s get into the weeds.

Initial Situation: The Challenges Fair.com Faced

Prasid: Paint a picture for us of the initial situation.

Shaun: When I joined, Fair.com’s marketing team was tiny—just a few brand marketers. We had no structured performance acquisition, no lifecycle marketing, and no scalable customer acquisition strategy beyond referrals. The problem was, once we started buying ads, we had no way to make them effective at scale.

We needed a way to bring in new customers without inflating CAC, and we couldn’t afford to spend months on engineering-heavy custom solutions.

Aditya: Why was this crucial at that moment?

Shaun: Fair.com had just launched, and we needed predictable growth to prove out the business model. Without scalable paid acquisition, growth would stagnate. If we didn’t crack this problem early, we risked either overspending on acquisition or running out of new users to onboard.

Implementation: The Technical Marketing Stack That Powered Growth

Prasid: You’ve already told us that the big unlock was to create thousands of individual ad units with specific cars that were currently available on the platform. So tell us more about how you built this.

Shaun: The key was automating the entire process. Here’s how we built it:

1. Data Integration: We pulled real-time vehicle inventory from our internal databases and formatted it into structured datasets.

2. Automated Creative Generation: We used Smartly to dynamically generate ad creatives, overlaying real-time pricing onto professional car images.

3. Deep Linking: We leveraged Branch to create custom deep links, taking users directly to the relevant car listing inside the Fair.com app.

4. Programmatic Deployment: The ads were pushed automatically to Facebook and Google, ensuring we showed the right car to the right person at the right time.

This system eliminated the need for a manual creative pipeline while maintaining high-quality, highly relevant ads.

Outcome: The 90% CAC Reduction

Aditya: HowI love this so much. Can you share more about the results?

Shaun: The impact was massive. Our cost-per-pre-approval, which was our leading indicator of marketing efficiency, dropped by 90%. Instead of targeting broad audiences with generic creative, we were delivering personalized, high-intent experiences that converted at a much higher rate.

Prasid: Did you continue iterating on this approach?

Shaun: Definitely. As we scaled, we refined our dynamic creative strategy to improve engagement and conversion rates. We introduced A/B testing on ad variations, experimented with different price anchoring strategies, and fine-tuned how we retargeted users who engaged but didn’t convert.

Lessons Learned: Takeaways for Growth Leaders

Aditya: What were the biggest takeaways?

Shaun:

• Automation unlocks scale. Manually creating thousands of personalized ads is impossible. Automating that process was the key to making it work.

• The closer you get to real user intent, the better your results. Showing real, available inventory instead of generic ads made a huge difference.

• Growth Ops is about making things happen despite constraints. We didn’t have a huge engineering team, but we found creative ways to execute.

Prasid: Any predictions for the future of Rev Ops?

Shaun: Rev Ops will only become more critical. Companies will need marketers who understand data, automation, and engineering to scale efficiently. The best growth leaders will be the ones who can bridge those gaps.

Aditya: If you were advising a company facing a similar challenge, what’s your top piece of advice?

Shaun: Invest in automation early. The earlier you can eliminate manual bottlenecks in growth, the faster you can scale efficiently.

If you’ve ever ended a day of back-to-back meetings thinking “Sigh. Now I have to sit-down and send-out everyone’s action items” —this post is for you.

Meetings are where decisions are made—but too often, that’s where they stay.

After hours of back-to-back calls, we all walk away with action items that feel like smoke: you saw them, they existed, but they vanished as soon as the Zoom window closed.

So I built a system to fix that.

Using Fathom, Zapier, Asana, and Slack, I created a lightweight, AI-powered assistant that helps me track what got said, what needs doing, and who’s responsible—without adding any extra manual work.

It’s not perfect. But it’s already saving me hours each week and closing the gap between talking about work and actually doing the work.

Here’s how it works—and how you can set it up too.

⚡Want the Zap templates I’m using? Comment “Fathom” and I’ll send over the exact workflows with screenshots.

The Problem

I work across multiple companies, and so in addition to back-to-back meetings, I’m also trying to jugle context-switching across multiple businesses, project management tools, and Slack instances.

There are tons of AI-powered Meeting Notes tools, but I wanted more than clean summaries and recordings.

What I really needed was a way to automatically extract action items and push them into our actual project management tools so they live-on past the meeting.

I want to:

• Extract action items from meetings (mine and my team’s) — assigned and ready for triage

• Push those tasks into Asana, where we actually manage work

• Send summaries to Slack, where that we maintain momentum in-between meetings

• Do all this without my involvement every time

The Stack

Here’s the tools stack I came up with:

• Fathom – An AI-powered note-taker that records, transcribes, and summarizes Zoom or Google Meet calls.

• Zapier – Glues everything together and connects apps like Fathom, Slack, and Asana, triggering workflows based on events.

• Asana – My team’s primary task management tool.

• Slack – Where summaries get visibility and where we share updates, insights, and decisions in real-time.

With these tools working together, every meeting becomes a launchpad—not just a memory.

Building the System

Here’s what happens after every meeting:

1. Fathom records and transcribes the call.

2. Fathom’s AI generates a summary and action items

3. Zapier catches the new summary and:

• Pushes the full summary to a Slack channel (usually #meeting-notes or a workstream-specific channel)

• Pushes each action item to a designated Asana board

1. The tasks land in the “Preparing” column, where my Chief of Staff and I review them in our daily sync.

2. Every task is tagged “Fathom” so I can quickly filter, triage, and audit what the AI surfaced.

Here’s what my v1 Meeting notes Slack post looked like:

It looked pretty clunky, so here was a cleaned-up v2:

Each of those bullet points deep-links to a spot in the Fathom meeting recording:

Business Impact

Some of the benefits of pushing the note and action items into Slack:

• Seeing the action items in Slack provides a little nudge that pushes folks to maintain momentum in-between meetings

• The extended team who couldn’t attend has visibility into what happened without watching an hour-long recording

• It builds a transparent knowledge loop across departments

This has helped reduce the number of unnecessary check-ins and “hey, what was the outcome of that meeting?” messages across our teams.

I also love that we’re pushing Action Items into Asana: it’s cut the time I spend writing-up action items by 75% - now I just have to tweak (and sometimes delete extraneous) action items directly in Asana.

What’s Working (and What’s Not)

The Fathom → Slack integration took some tweaking via Zapier. The summaries initially came in messy, but after some testing, I got them formatted cleanly with consistent formatting and the right Slack mentions.

The Fathom → Asana integration, however, worked out of the box. Tasks get created with:

• The meeting title (if included)

• Assigned owner (if Fathom detects one)

• Notes, links, and due dates (if mentioned)

That said, Fathom can be a little generous when it comes to action items. It often overidentifies tasks, so we’ve gotten into the habit of doing a quick review. Still—too many is better than none.

I push everything into the shared board that my Chief of Staff and I review every day. Specifically, into a “Preparing” column, where we triage and assign them during our daily check-ins.

By tagging all tasks with “Fathom”, we can filter for just those items, clean up false positives, and turn the real ones into owned deliverables.

Edge Cases and Limitations

One thing I’m still testing is multi-org usage. I work across 3–4 companies, each with different meeting platforms and logins. Can Fathom handle multiple Google Meet and Zoom accounts?

So far, the desktop app seems like it might handle this better than the browser extension.

Another challenge is routing notes and tasks to the right workstream. Ideally, I’d love for:

• Product Marketing meetings → Client’s PMM Team Slack + Asana board

• RevOps meetings → Client’s RevOps Team Slack + Asana board

• Internal meetings → Internal Slack and Internal Asana instance

Bonus: Route Summaries to Specific Channels or Workstreams

I’ve thought about a solution here but haven’t implemented it yet. It should be easy to dynamically route notes/actions using the meetings attendees or the meeting name.

The way I would do that would be to add workstream prefixes into meeting titles, like:

• [RevOps] Q2 Pipeline Review

• [PMM] Feature Feedback Call

If you did that, you could add a if/else function in Zapier that could pick-up the prefix and route the notes + tasks to the correct Slack instance / channel and the correct Asana instance / project board.

Cost and Setup Time

• Fathom has a solid free plan, but you’ll need the paid tier (~$XX/month) to unlock Zapier integration.

• Setting up all the zaps took me ~1–2 hours end-to-end. If you’re familiar with Zapier, it’s straightforward. If not, I’ll be sharing the exact workflows I use.

I’ll continue refining it—but even in this early state, it’s a force multiplier.

Want the Zap templates I’m using?

👇 Just comment “Fathom” and I’ll send them over.

This isn’t a post about SaaS or CAC—but stay with us.

Lately we’ve been fascinated by the online community #BookTok.

#BookTok has completely disrupted the publishing industry’s go-to-market model, and if you sell anything—books, tools, software, services—you should be paying attention.

We wanted to understand: What can #BookTok teach us about how to modern consumers making buying decisions?

• How did #BookTok disrupt publishing?

• What worked and what didn’t?

• And what all of us can learn about selling online in 2025.

#BookTok Created A New P2P Path to Product Discovery

For years, book sales were in-decline, with publishing execs insisting it was because people just didn’t read anymore.

The publishing industry used to control the entire go-to-market:

• Controlling who gets published - publishers have always had the power to control which authors and stories get published at all

• Controlling bookshelves - they use retail relationships to influence what gets bought and stocked by retailers, as well as how books are merchandised with in-store displays

• PR engineering - the industry helps authors record months of interviews in-advance, all to be released the week the book launches

• Bestseller list manipulation - use pre-sales and bulk-buys to juice the sales numbers during opening week

And for a while, that worked.

But what BookTok has shown us in recent years is that there’s far more demand for books than publishers realized - but that demand has shifted away from the top-down books that the industry pushes through it’s machine, into different books that gain traction thanks to a groundswell from the community.

When BookTok loves a book, it moves.

Not because it was marketed.

But because it was felt.

But BookTok exposed a fundamental truth: publishing never had a demand problem. It had a discovery problem.

Readers weren’t ignoring books—they just weren’t discovering them the way publishers expected.

It turned out people were reading—they just weren’t finding books through critics, legacy media, or Amazon’s algorithm. They were finding them through raw, emotional recommendations on TikTok.

How #BookTok Turns “Dead” Books Into Bestsellers—Years After Their Release

Traditional publishing puts expiration dates on books. If a title doesn’t hit within the first few months, it gets pulled from front shelves, buried in back catalogs, and forgotten.

But the community on #BookTok doesn’t care when a book came out. If a reader picks it up, gets destroyed by the ending, and films themselves sobbing into the camera—that book starts moving.

Exhibit A: The Rise of the Hooververse

Colleen Hoover self-published her first novel, Slammed, in 2012. For most of the 2010s, she maintained a solid—but relatively niche—presence in the indie romance scene. Her books performed well in Kindle categories and she built a loyal fanbase, but she wasn’t a household name.

Then TikTok happened.

In late 2020 and early 2021, BookTok creators began posting emotional, teary-eyed reviews of It Ends With Us—a novel she published back in 2016. Videos with titles like “this book destroyed me” and “I can’t stop crying” went viral. The #ColleenHoover hashtag quickly ballooned into the billions of views.

What happened next was unprecedented:

• Hoover sold over 14.3 million books in 2022 alone, across both frontlist and backlist titles.

• Six of her titles appeared on the New York Times Top 10 Bestseller List simultaneously—a feat almost unheard of for a living author.

• And according to Publishers Weekly, her own BookTok content helped fuel the fire:

“Take Colleen Hoover and her nearly five billion views on TikTok for example. As I see it, Hoover’s popularity is, in large part, due to her viral videos on TikTok.”

@todayshow#booktok has been a CRAZY part of @Colleen Hoover success as a writer. She says that readers on TikTok helped her books go viral. #itendswithus #todayshow

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Her backlist wasn’t just selling—it was dominating. Ugly Love (2014), November 9 (2015), Verity (2018), and Reminders of Him (2022) all surged in sales, with TikTok readers devouring her entire bibliography in rapid succession.

TikTok didn’t just make It Ends With Us a hit—it created the Hooververse, a shared universe of emotionally explosive novels that readers now treat like a lifestyle.

Exhibit B: The Song of Achilles by Madeline Miller

• Published in 2011

• Sat quietly on shelves for nearly a decade

• Then in 2021, it exploded on BookTok

There was no movie adaptation. No celebrity endorsement. No publisher-led re-release. It won the Orange Prize for Fiction in 2012, which gave it some acclaim—but it didn’t hit NYT bestseller status until 2021, after going viral on BookTok.

It was this single TikTok video below, posted by user Selene Velez @moongirlreads_ in 2021 where she featured The Song of Achilles in a video she called “books that will make you SOB”:

@moongirlreads_Reply to @justmemyshelfandi #books #booktok #fyp #foryou #ya #reading #sad #bookrecs

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The video has over 6M views.

And yes, Selene’s video featured five books, not just The Song of Achilles—but Achilles was the emotional climax of the video, and the one that stuck with viewers (and dominated the comments). The video became known in the BookTok community specifically for that moment, where Selene said: “I can’t think about it without bawling.”

That line got duetted, stitched, and quoted across TikTok. It became meme-fied.

Several outlets have cited this specific video and creator as the moment Achilles began trending. For instance:

• The Everyday Magazine mentions @moongirlreads_ as the origin point.

• Publishers Weekly confirms the book’s NYT charting happened after BookTok attention.

The other titles mentioned didn’t go nearly as viral. Why?

• The Song of Achilles had the perfect BookTok formula: tragic romance, Greek mythology, high emotional payoff, lyrical writing.

• The emotional impact matched BookTok’s culture of obsession, heartbreak, and identity-building.

• Other books in the video lacked that same shared catharsis, or already had saturation elsewhere (some gaining momentum from Goodreads before TikTok).

Here’s another video from the same user talking about the same book:

@moongirlreads_#greenscreen cried so much it landed me in the NYT 🥀💧🚶‍♀️#readers #tsoa #brocken #moongirlreads #sadbook

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These videos turned into a template for other users, usually creating content along the lines of “Books That Ruined Me,” where Achilles consistently ranked #1.

These viral posts became a movement, and suddenly, this quiet 10-year-old novel reached the #1 spot on the New York Times bestseller list.

TikTok didn’t just sell this book—it resurrected it.

Exhibit C: A Little Life by Hanya Yanagihara

• Published in 2015.

• Acclaimed, nominated for awards, but never a mainstream blockbuster.

• Until 2022, when TikTok turned it into an emotional battleground.

This book is trauma with a spine—a gut-wrenching, deeply harrowing story of friendship and pain. Some BookTok users sobbed over it, calling it life-changing. Others labeled it “trauma p*rn” and debated whether it was too much or emotionally exploitative.

The book became one of the most discussed titles on the platform—and that drove a serious sales resurgence:

• TikTok videos under the hashtag #alittlelife have surpassed 116 million views (as of April 2025)

• According to Penguin Books UK, A Little Life became a top-selling backlist title again in 2023 thanks to BookTok-driven sales

• Waterstones, one of the UK’s largest bookstore chains, highlighted the book as a recurring bestseller in their #BookTok tables

• Viral TikToks like this one from @kierralewis75 sparked massive conversation and stitched responses

@kierralewis75#alittlelife #booktok #hanyayanagihara

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By 2024, A Little Life was not just back—it had become one of BookTok’s most polarizing, talked-about, and commercially successful revivals.

Love it or hate it, people couldn’t stop posting about it.

And if people are talking? People are buying.

Other BookTok Resurrections Worth Knowing

One pattern that emerges when studying other examples of this phenomenon: the books that are resurrected are often emotionally explosive, narratively intense, and tailor-made for obsession.

And the stories readers cling to? They’re often about identity, loss, redemption, and love in its most complicated forms.

1. They Both Die at the End by Adam Silvera (2017)

This YA novel had a modest release in 2017—well-reviewed, but not a breakout hit. It wasn’t until 2020, when TikTok users began posting tearful, heart-wrenching reactions to the ending, that the book took off.

@abbysbooksi wasn't disappointed with this one #theybothdieattheend #recommendations #fyp #contemporary

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And the numbers back it up:

• In 2021, the book hit #1 on the New York Times YA Bestseller List—four years after publication.

• It stayed on the NYT list for over a year straight.

• Sales surged from under 5,000 units/week to over 20,000 units/week at peak, according to NPD BookScan.

• The chart from BookScan shows a clear inflection point: when BookTok got a hold of it, sales skyrocketed.

2. It Ends With Us by Colleen Hoover (2016)

BookTok didn’t just revive this novel—it turned Colleen Hoover into a publishing juggernaut resulting in the recent It Ends With Us film adaptation starring Blake Lively and Justin Baldoni.

@newlynova#colleenhoover fans, are u okay? do you want to borrow my weighted blanket? #verity #booktok #newlynova #bookrecs

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BookTok operates on emotional imprinting. Readers posted thousands of teary-eyed reviews. That emotional intensity created a kind of author addiction—when readers get emotionally attached to one book, they go hunting for everything else by that author.

Check out how BookTok has impacted the rest of how Colleen Hoover’s catalog:

• Over 5 billion views on TikTok mentioning #ColleenHoover.

• Over 14.3 million books sold in 2022 alone

• At one point, six of her books were simultaneously on the New York Times Top 10 list.

• Her sequel, It Starts With Us, became Simon & Schuster’s most pre-ordered book of all time, with 800,000 copies sold on launch day.

3. The Seven Husbands of Evelyn Hugo by Taylor Jenkins Reid (2017)

This novel quietly simmered for years—until BookTok started calling it “the queer love story you’ll never forget.” Everybody was so obsessed with this book, reading it everywhere and going viral on TikTok.

@bijondina#evelynhugo #airport #taylorswift

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Though critically acclaimed upon its 2017 release, The Seven Husbands of Evelyn Hugo didn’t achieve mainstream blockbuster status until BookTok users began spotlighting it as a must-read.

What followed was a perfect storm of obsession:

• The hashtag #evelynhugo has over 550 million views on TikTok.

• Users film “I just finished this and I’m emotionally wrecked” reaction videos that get hundreds of thousands of views.

• Quotes from the book are everywhere on BookTok and Pinterest.

• Sales surged so dramatically that the book returned to the New York Times bestseller list five years after publication.

• As of 2022, it was the 2nd most-sold adult fiction book in the U.S. behind only It Ends With Us (NPD BookScan).

4. Aristotle and Dante Discover the Secrets of the Universe by Benjamin Alire Sáenz (2012)

This YA classic about queer Latino identity was rediscovered by Gen Z through BookTok’s love of poetic coming-of-age stories.

@toad_pitstopI know its been a WHILE but had to come back because… THERES A MOVIE #booktok #annotatingbooks #annotatedbook #booktiktok #bookworm #arianddante

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Originally released in 2012, Aristotle and Dante was beloved in literary circles but flew under the mainstream radar. It won awards. It built a small but devoted following. Then, a decade later, TikTok found it—and everything changed.

What happened next:

• TikTok creators began posting emotional reviews under hashtags like #aristotleanddante and #bookswithbeautifulwriting, many racking up hundreds of thousands of views.

• The book’s most viral themes—loneliness, masculinity, queer tenderness—struck a nerve with Gen Z readers navigating their own identities.

• Sales surged leading up to the 2022 film adaptation, with publishers re-releasing special editions to meet demand.

• As of 2023, the book had sold over 1.5 million copies, with the sequel (Ari & Dante Dive into the Waters of the World) becoming an instant bestseller.

5. Throne of Glass by Sarah J. Maas (2012)

Sarah J. Maas isn’t just an author—she’s a genre on BookTok. Her books consistently trend on #BookTok with fantasy fans posting reaction videos, fan art, and deep lore breakdowns.

@jordan_fisherPSA #booktok #throneofglass #sarahjmaas

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Throne of Glass, the first book in her fantasy series, was published in 2012 and saw steady sales over the years. But a decade later, BookTok turned Maas into something else entirely: the Beyoncé of fantasy romance. Her books aren’t just read—they’re devoured, analyzed, memed, wept over, and endlessly re-shared.

What the numbers say:

• The hashtag #sarahjmaas has over 4 billion views on TikTok.

• Fan-made videos about Throne of Glass, A Court of Thorns and Roses, and Crescent City routinely hit millions of views, driving new readers into entire book universes.

• From January to June 2024, Maas sold 4.83 million print books in the U.S. alone, much of it attributed to BookTok virality.

• Booksellers now create entire shelves dedicated to her books—because customers don’t just want one title, they want the full Maas cinematic universe.

Key Takeaway: BookTok rewards bingeable storytelling. When readers fall for a world, they want more of it.

A Pattern Emerges

After looking at all seven books, here’s what becomes crystal clear: BookTok is a behavior shift. And the ripple effects go far beyond a single viral title:

1. One Viral Book Unlocks the Whole Backlist

• BookTok didn’t just elevate It Ends With Us—it triggered a Hoover binge. TikTok made “reading everything an author ever wrote” a common consumer pattern.

2. Deep Emotional Response Fuels Long-Tail Sales

• The Song of Achilles and A Little Life prove that emotional impact—not recency—drives virality.

• These books were 6–10 years old when they went viral, with no new promo. What moved them? Readers crying on camera, sharing emotional reviews.

3. Fan Culture > Formal Criticism

• Evelyn Hugo wasn’t initially marketed as a viral must-read or queer romance. When it was first published in 2017, it was positioned as historical fiction with a Hollywood twist—a literary novel about a reclusive film icon finally telling her life story. It earned solid reviews, but didn’t become a blockbuster. BookTok rebranded it as “the queer love story you’ll never forget.”

• Sales spiked five years post-publication. TikTok made fan discourse more influential than editorial reviews.

4. BookTok Can Reframe an Entire Genre

• Aristotle and Dante didn’t just go viral—they helped revive poetic, queer, coming-of-age Young Adult fiction. It wasn’t just a book trending—it was a new appetite emerging in public.

5. One Author = A Whole Category

• Sarah J. Maas created an entire subgenre (romantasy). BookTok treated her catalog like a universe.

6. Viral Word-of-Mouth Creates Sustained, Multi-Year Growth

• They Both Die at the End wasn’t an instant success until TikTok got a hold of it. From there, the growth wasn’t just a spike —it has been a sustained increase lasting multiple years.

• TikTok’s emotional reactions didn’t just trigger a bump—they redefined the life cycle of a book. Instead of fading after 6 months, titles now experience a second wind years later, powered by peer-to-peer obsession.

The Old Way vs. The BookTok Way

For generations, the industry functioned as a gatekeeper. The publishing house decided what books had merit. The bookseller decided what got shelf space. The critic decided what was worth reading.

But BookTok flipped that model.

Now, the reader decides.

And when the reader decides, everything changes:

The winners aren’t the ones with the biggest budgets.

The winners are the ones who create the deepest connections.

BookTok Created a Whole New Sales Curve

The chart below shows total U.S. print unit sales of BookTok-featured authors from 2019 to 2023. According to NPD BookScan, these authors are defined as those whose books have trended on TikTok—typically via the #BookTok hashtag, viral creator posts, or retail campaigns tagging them as BookTok titles.

Here’s what we’re seeing:

• 2020: 13M units sold — up +28% over 2019.

• 2021: 27M units — up +106% YoY.

• 2022: 47M units — up +71% YoY.

• 2023: Holding strong, with 23% YTD growth through July and seasonal lift expected in Q4.

Key takeaway: BookTok isn’t just launching individual bestsellers. It’s raising the floor for all books that trend on the platform.

Even as media trends shift and pandemic-era reading patterns normalize, the TikTok-driven discovery loop continues to compound author visibility and backlist sales.

And no, this isn’t happening everywhere. The same report shows that non-BookTok authors didn’t see this kind of growth, suggesting the spike isn’t industry-wide—it’s platform-specific.

Bookstores Are Thriving

BookTok is also bringing younger readers back to physical bookstores. Inside, you’ll see BookTok shelves and tables front and center.

Barnes & Noble is opening 60 new stores in 2025. This will surpass the bookstore chain’s record of 57 openings in 2024. That’s a significant turnaround after more than a decade of downsizing, during which the company closed 150 locations between 2009 and 2019. Foot traffic at Barnes & Noble has been rising every month. People aren’t just buying books—they’re going back to bookstores.

Also Bloomsbury’s profits shot up 220%—the first year BookTok took off. Coincidence? Not a chance.

#BookTok’s Biggest Winners and Losers

Some brands saw what was happening and adapted.

Winners:

1. Barnes & Noble

For over a decade, Barnes & Noble was shrinking—closing stores, losing ground to Amazon, and quietly fading into the background.

Then BookTok happened, and Barnes & Noble leaned into it—hard. They:

• Rolled out dedicated #BookTok tables in nearly every U.S. store

• Launched BookTok-branded sections online

• Let readers dictate what went on display—turning stores into fan-curated discovery zones

And it worked.

Foot traffic is rising month after month, and their #BookTok tables consistently rank among top-performing in-store displays.

What Can We Learn?

Retail has been in secular decline for years—but that doesn’t mean the products themselves are dead. What’s fading is centralized discovery.

TikTok makes it easier than ever to find and engage with passionate micro-communities.

Barnes & Noble succeeded by giving a digital fandom a physical home.

That’s the playbook: If you’re in retail, ask yourself—Is there a way for us to be a physical home for an existing vibrant community?

2. The Folio Society

The Folio Society is a publisher that specialized in collector’s editions—hardcovers designed to be gorgeous. We’re talking:

• Cloth-bound hardcovers

• Foil-stamped slipcases

• Commissioned illustrations

Think of it as the Criterion Collection of publishing.

They were known for producing elevated editions of literary classics—Shakespeare, Austen, Tolkien. But they weren’t exactly built for viral trends.

But when BookTok’s obsession with fantasy exploded, they pivoted.

As fantasy and romantasy took off on TikTok, The Folio Society noticed something: unboxing videos were going viral. Readers weren’t just emotionally wrecked by the story—they also wanted to own a beautiful physical object that reflected how the book made them feel.

So what The Folio Society did:

• They expanded their catalog to include BookTok darlings like A Court of Thorns and Roses, Dune, and The Song of Achilles

• Leaned into aesthetic-driven sales, designing covers that would pop in TikTok feeds and on “Bookshelf Tour” videos

• Prioritized limited runs with high price points (some editions retailing up to £1,000)—and they sold out

According to CEO Joanna Reynolds in an interview in The Guardian, fantasy and sci-fi were “gamechangers,” and their market under 25 is now nearly as large as their traditional over-65 audience. One unboxing video for The Song of Achilles helped the edition sell out within weeks—and it now has over 2 million views across platforms.

@loverofpagesmaybe its time to finally read this book?! 🏹 #booktok #thesongofachilles #bookish #fyp @The Folio Society

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Sales have increased 55% since 2017–18, driven largely by this younger, online-first, fan-oriented audience.

What Can We Learn?

BookTok uncovered a market of deeply passionate fans who were underserved by the premium end of the market.

How can we extrapolate this trend to other markets that might have these dynamics?

I quote James Clear the way others quote Taylor Swift. Should his book also be on The Folio Society? Is there an opportunity to sell me concert tickets and passes to meet James Clear?

Gweneth Paltrow has GOOP home products. Will we see the rise of home goods brands from TikTok celebs? Should Target have a section for influencer-endorsed picks?

3. Little, Brown

Little, Brown is a publisher that partnered with BookMachine, a TikTok-savvy marketing agency, to run a campaign that combined influencer partnerships, paid ads, and real community engagement.

There’s no way to know for sure which book their campaign promoted, but best guess is that it was Circe by Madeleine Miller. Check out some of the #BookTok videos posted around then:

@_the.twilight.zone_Annotating Circe by Madeline Miller #Circe #MadelineMiller #Booktok #annotatingbooks #annotating #annotations #fyp

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@aymansbooksheart? shattered #circe #thesongofachilles #madelinemiller

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The Strategy

• Micro-influencer seeding. BookMachine handpicked creators under 10k followers—BookTok’s most trusted voices—and put the book into their hands. These creators are the emotional heartbeat of the platform: high engagement, niche trust, no performative gloss.

• Paid amplification. Once content started organically performing, BookMachine backed the best videos with strategic TikTok ad spend, targeting similar audiences based on engagement patterns.

• Organic storytelling. The creators weren’t given talking points. They were given books. The reactions—crying, gasping, ranting—were authentic. TikTok’s audience doesn’t want polish. It wants pain, obsession, and ugly crying. The campaign delivered.

• Publisher-owned content. During the campaign, the account saw an 84% increase in followers, with improved organic reach and engagement.

The Results

• The title featured in the campaign jumped 1,600+ spots on Amazon’s bestseller rankings, going from near-invisible to must-read.

• Influencer videos hit hundreds of thousands of views, driven not by polish—but by genuine emotional reactions.

• The content didn’t feel like marketing. It felt like obsession. Which is exactly what sells on TikTok.

Losers:

But there are those that treated BookTok like just another ad space—and not every viral hit delivers.

In the rush to cash in, some publishers and authors are pushing books to market too fast, leading to a flood of under-edited, formulaic releases that don’t live up to the hype.

1. These Violent Delights by Chloe Gong

   • Blasted for grammatical errors and poor editing

   • Left fans disappointed in what was supposed to be a high-caliber BookTok recommendation

2. The Spanish Love Deception by Elena Armas

   • Hailed as a must-read romance, but slammed for shallow characters and predictable tropes.

   • Readers expected something fresh but got the same overhyped formula.

The result? BookTok is powerful, but it’s also ruthless. A viral boost can sell thousands of copies fast—but if the book doesn’t deliver, readers won’t stay quiet about it.

The key takeaway? You can’t buy credibility on BookTok. You can’t manufacture trust. You can only earn it.

The TikTok Stats That Actually Matter for Marketing

“The reason TikTok is a great place for book promotion is due to a simple formula: algorithm + community + trends. The algorithm brings your bookish content to readers who have similar interests to you, which has helped the community element of BookTok to grow super fast. Following trends allows the content to feed into the larger picture of popular culture. This creates an accumulative effect of growth that results in more interest and “hype” around the book you are promoting. If you know how to work this formula to your advantage, you’re ahead of the game.”

— Niamh Wallace, BookTok creator (@booksarebrainfood) and BookMachine Marketing Executive

Everyone knows TikTok is big with over 1Bn users.

• Users spend an average of 1.5 hours per day on the app, which is 2x the time spent on Facebook or Instagram, and 3X that of Twitter.

• Comparison with Instagram: Micro-influencers (under 10K followers) average 18% engagement → Compare that to Instagram’s 4%. Smaller creators = bigger impact.

• Comparison with Goodreads: In contrast, Goodreads, a leading book recommendation platform, receives approximately 87.3 million visits over a three-month period, averaging around 29 million monthly visits.

If you’re in marketing, startups, or building anything that requires people to care, here’s what you should learn from BookTok:

1. Extreme Emotion wins. Consumers trust raw, authentic, emotion. You want products and experiences (and influencer messaging) that is extreme.

2. Micro-influencers > traditional ads. TikTok’s algorithm doesn’t heavily weight follower count—it prioritizes engagement. That means content from a passionate micro-influencer with 10K followers will likely drive more impressions than a bland endorsement from a celeb with 5 million followers. When everyone starts on a level playing field, authenticity wins.

3. Sell emotional transformation, not products. People aren’t buying a drill - they are buying the holes it makes. With books—they are buying heartbreak, healing, identity, catharsis. You’re selling an emotional experience with a before and after.

4. “New” Matters Less than “New to Us” - There’s been plenty of discussion about how we are converging on a global monoculture - K-pop and watch bollywood films transcend geography. You can get avocado toast for brunch all over the world.

Our 3-dimensional world has collapsed-into a monoculture, and perhaps the fourth dimension (time) is next. BookTok shows that people are very happy to buy a 10 year old book even through it’s not “new” as long as it’s “new to us.” They care more about quality within their niche than broad-based newness.

Just this week, with The White Lotus ending, my wife started watching Mike White’s 2011 TV show Enlightened. I think we’ll see this trend more and more.

As a consultant, I’m often parachuting into businesses where growth has been stagnant or in-decline for a while. When I worked for growth-stage startups, there were plenty of times where we were months away from death, and I was the person most-accountable for driving the revenue that would save us. If I synthesize what I’ve learned, here’s the playbook I’d follow in a turnaround — I’d love to hear what you’d add.

Rough outline of the playbook is as follows:

1. Start Shipping One Thing

2. Build a Growth Model

3. Spot Leaks, Pools, and Overflows

4. Run a Roadmap Prioritization Session

5. Communicate Your Top 2 Priorities—and What Fires to Let Burn

6. Focus on Unlocking New Opportunities Over Paying Down Debt

7. Organize Pods and Pod Leaders, and Growth Meeting Around Each Lever

8. Set up a Growth All Hands Meeting for Team Leads to Present

9. Plug Talent Gaps with the Right Mercenaries

Now let’s get into the weeds.

1. Start Shipping One Thing

In a turnaround situation, every day matters. So probably within the first 2-3 days I’d align with my CEO on one thing that’s a top priority (usually a funnel step in the existing GTM motion that’s floundering). You don’t have time to get to 70% information (let alone 100%), so I’d push the existing team to download context then lean heavily on my own intuition. Next, I’d pick one thing, and get the team going on that one biggest opportunity straightaway. This would help to build momentum and hopefully extend our runway so we can keep learning.

2. Build a Growth Model

Understanding Layers and Levers

In order to have a data-driven approach, you need a growth model. You don’t have a ton of time to make it perfect, but I’d try to create a simple 1-sheet version in week 1.

A growth model is totally different from a financial model: financial models show lagging indicators (i.e. Revenue Recognized in the month). But a Growth Model is about assumptions, inputs, and leading indicators (i.e. new leads acquired and new customers closed that Month).

First, map out a high-level funnel and get baseline historical data for the last ~12 months. The goal is for v1 to fit on a single sheet, and have perhaps 4-5 funnel layers (i.e. Media spend, Site Visits, Leads, Purchases, Revenue) and 4-5 “levers” (i.e. CTR, Lead Capture Rate, Purchase Rate, and LTV).

Think of Levers are the conversion rates between Layers. If you can ship projects that improve a Lever, you’ll improve all the results in all the Layers below it.

Note: Make sure to consider if there are any major “axes of difference” within the business that must be modeled separately in order to understand what’s happening.

Example: if you have a cash cow product that’s mature, and 3 experimental products that are just getting going, looking at blended CAC and blended conversion rates may not be helpful. You might need to build the model as two separate branches that come together at the end (i.e. in this example I’d build 1 branch for the cash cow, and 1 branch for the other 3 combined, and then sum them at the bottom).

Don’t Overlook How Time Is Being Allocated

An oft-overlooked area is to also think about the rough time-allocation of team. Try to understand how your headcount is distributed across channels, product lines, and regions? This uncovers misallocations and areas ripe for optimization.

3. Spot Leaks, Pools, and Overflows

Now you’re ready to start analyzing what your growth model is telling you. The goal of this is to identify 5-10 hypotheses for areas where you can optimize. Each one of these hypotheses will need to be drilled-into and investigated. You should be capturing all these hypotheses as potential projects.

Leaks

Look for layers of the funnel where you see a big drop-off. One common example—at Coding Dojo, we noticed that in the past quarter our sales demo call show-up rates had dropped by 50%. We’d sprung a leak!

When you spot a leak, zoom-in and get more data. As one-off, we pulled a ton of more detailed metrics. We studied the open rates and CTRs on the emails and SMSs that fired just after a meeting was booked, and just after someone no-showed.

After investigating, it became clear that when an interested prospect tried to book a demo, the next available timeslot was too far out in the future. If you’re shopping right now, and the next appointment is in a week, there's a good chance you'll find another provider that can talk right now.

Pools

Look for places where a lot of leads are pooling/getting stuck. Recently at another company we noticed the average speed-to-lead was quite high. When we zoomed in, we found leads were sitting for days without getting assigned to an SDR.

The cause? Turns out that someone (who probably long-since left the company) had created a rule that leads couldn't be assigned if they were missing a location field. (My guess is that at some point, SDRs might have been organized by region.) Because of the rule, SDR managers were manually adding a location to every lead, and leads were spending a half-day stuck at this step. Once we removed this step, leads got routed to an SDR in near real-time.

Overflows

Going back to our Time Allocation, look for places where there's a misalignment between resources and results. Example: I recently worked on a business that had a global marketing team of 40. Each region needed it’s own organic social team that spoke the local language. When I added them all up, I realized 25% our global headcount was allocated to a channel that drove zero revenue. We immediately started pulling those folks onto more-strategic projects where they could have more impact on the bottom-line.

Another example: A new product launch was a top priority for the product team, and was eating up a big chunk of the Marketing team’s bandwidth. That made sense when we were in “shoot for the stars” mode.

But now that we were in “grow revenue every month like your life depends on it” mode, we needed to reprioritize. We shifted the focus of our PMM to a repackaging/pricing project for our cash cow product. By making one of our upsells a bit more prominent in our pricing, we were able to grow our average sale price by double-digits.

Years later, that one small pricing change to the cash-cow is responsible for far more revenue than the new product ever produced.

4. Run a Roadmap Prioritization Session

Now that you’ve identified your leaks, pools, and overflows, it’s time to prioritize them.

I like the ICE framework—use t-shirt sizes. It's okay if the first go-round is mostly educated guesses. Knock it out in 2 hours or less. You'll be doing it again in another 2-3 months and you will have learned a ton in the interim.

5. Communicate Your Top 2 Priorities—and What Fires to Let Burn

What happens is that if you keep pointing to your top priorities—but don't tell people what they can drop?They'll still try to juggle everything.

If a CEO calls something a “low” priority, but it’s a pet project of one leader, resources might still go there. Horse-trading might still occur as the leader tries to bring it to reality. That horse-trading slows down the whole organization.

That’s why I love this idea from General Stanley McChrystal: “The best leaders are those who empower their teams by letting them know what’s okay not to do.”

Make it clear that you want zero progress on everything else, and clear the road for these 2 things to get done fast. Note: as a leader, it’s your job to run interference for your team with outside stakeholders, so they can say no to everything else.

Sidenote: why just 2 priorities (instead of the usual 3?)

In a turnaround we can’t afford to be multi-threaded. We need to put out the biggest fires right now. And that likely means surging on just 1 short-term and 1 medium-term problem at a time.

Selina Tobaccowala, a seasoned entrepreneur behind companies like Evite and SurveyMonkey, advocates for the concept of “letting fires burn.”

By deliberately allowing some fires to rage, leaders can direct their energy toward the fires that will kill us first.

6. Focus on Unlocking New Opportunities Over Paying Down Debt

I love this idea from Good to Great. Author Jim Collins argues you should put your best people not on fixing problems or paying down debt. Instead, put your top folks on unlocking the biggest opportunities. There will always be debt that needs to be paid down. But in a turnaround situation, you need revenue growth to eat first from the trough.

This seems obvious, but I often encounter good people, often conscientious, technical people, that have been at a company a while. They see all the debt that has accumulated and they want to attack that first (i.e. junk data in Salesforce that needs clean up, our documentation is woefully lacking, we need to migrate the whole system from old tool to new tool).

In a turnaround situation, you need to keep the team focused on shipping iteratively on things that unlock incremental revenue. If we do that, we will live to fight another day, and we will eventually be able to attack that debt.

A best practice for eng teams is to allocate 20% of our resources to paying down debt and protect the other 80% for unlocking new opportunities. That’s a good ratio to stick to.

7. Organize Pods and Pod Leaders, and Growth Meeting Around Each Lever

The mistake I see a lot of leaders make is they organize teams around functions (i.e. the performance marketing team works on all paid ads, the design team works on the design queue, etc.). Instead, break the funnel down in to levers, give each lever an owner, north star metric, weekly targets, and a slide where they have to present in front of the entire tribe.

Their weekly slide template should include:

• Lever: Grow Leads from Paid Ads

• Team Lead: Jean-Luc

• Members: Geordi, Beverly, Will, Deanna, Worf

• Volume Metric Target: 33 Sales Accepted Leads (SALs)/week

• Efficiency Metric Target: $100 Cost per SAL

• Graph of Weekly Performance

• Commentary: How, Why, So What

  • How: How are the numbers doing? How should we feel?

  • Why: Why are the numbers moving that way?

  • So What: What are we going to do about it?

  • What Shipped Last Week:

    • A list of the project shipped last week

Here’s what makes this so powerful:

How. Why. So What is the Engine that Drives a Data Driven Culture

Having the data is the beginning of being data driven. By looking at the data over time, everyone can see if we’re closing the gap to our goals.

The ‘Why’ forces us to make connections between the work we’re shipping and how the metrics are moving.

The ‘So What’ is an opportunity to reprioritize the roadmap, or to surface misalignments. Sometimes the “so what’ might be that we’re not going to do anything, because we’re focused elsewhere. That’s healthy.

Putting the whole team’s name on the slide

People are wired through millennia of evolution to care about acceptance by the tribe—there is tons of research showing that acceptance is a far more powerful motivator than money. In an organization with politics (i.e. all organizations) people form their own opinions about who is most accepted by the tribe - they’re motivation is to be agreeable and dole out favors. But when we create and share pod targets vs. actuals, we’re really creating a non-political, objective scorecard for who deserves acceptance. We’re defining the rules of acceptance for the tribe as shipping —and hitting these targets.

Putting projects next to metrics

In a lot of organizations, the “what” is divorced from the “how” - we look at numbers that are good or bad, and then we go back to our pet projects. If the numbers are down, and the team immediately pivots to talking about a project that has no hope of moving the needle in the next future, it’ll become pretty obvious. They end up course-correcting on their own, or getting uncomfortable questions from me.

8. Set up a Growth All Hands Meeting for Team Lead’s to Present

Early in my career the mistake I made is that as the Head of Marketing, I felt like I had to do all the analysis (and all the presenting) alone.

Today I make sure that it’s the pod leaders that are doing all the talking. If they’re out, someone else from their pod fills-in.

This is the most powerful motivator. Tou want to be able to explain to the tribe what’s going on. And ideally you want to bring the tribe good news.

9. Plug Talent Gaps with the Right Mercenaries

Bring in Experienced Consultants for Immediate Impact

Now your team is at least rolling in the right direction and you’re on your way to stabilizing the business in the short-term. But now you also have the medium-term to worry about.

Startup marketing teams are often overweight on young hungry people with little experience, and underweight on experienced mercenaries. If one of your top 3 things isn't getting done extremely well once you re-allocate resources there—it's because you don't have the right people. These are the spots to start bringing-in mercenaries.

Why Mercenaries

Full-time hiring takes too long. I don't like agencies much because you're really getting 1 hour of the senior person's time and then 10 hours of junior people's time. I much prefer consultants. They know they have to self-onboard and deliver value almost immediately. And to get hired they’re constantly having to prove they are experts at their craft, and constantly learning from multiple companies at once. The result: they are typically sharper and more-current than FTEs.

How to hire mercenaries

I look for someone who comes through a referral and has done this exact thing 3x before. I look for people that are comfortable with month-to-month contracts, and they have to teach me things I don't already know in the interview process. I don't mind hiring expensive people.

Most importantly—I make clear how I'll be measuring success in terms of metrics. It's a red flag if they want a 6-month contract right off the bat. It's a red flag if they need more than 2 weeks to onboard. The right type of mercenary will put a ton of pressure on themselves to prove their ROI.

Final Thoughts: Turning Chaos into Clarity

A turnaround can feel overwhelming, like there are fires to put out in every corner. But by focusing on just 2 priorities at a time and letting everything else burn, by marshaling all your resources behind just a few things, and by building a data-driven culture with a sense of urgency, you’ll start to see clarity through the chaos. Week One is about setting a foundation that lets everyone pull in the same direction, building a rhythm that aligns daily actions with growth goals.

Ultimately, the key is to avoid getting bogged down by every small issue or every past inefficiency. Instead, channel your energy into the areas that drive results and trust your team to execute with focus and intent. The work done in this first week will not only stabilize the business but will also create a lasting roadmap for sustainable growth.

With JP Morgan now saying we've got a 60% chance of recession, I wanted to share some of the plays i'm running with the companies I advise to keep growing during a pull-back.

Case Study: 3 Tactics that helped Coding Dojo 3X Revenue During a Market Pull-Back

Prasid helped us align our marketing and sales orgs and better-leverage data and tools to unlock dramatic revenue growth. Prasid was instrumental in growing our revenue and in hiring a word-class marketing team.

- Richard Wang, CEO of Coding Dojo

Despite the market for coding bootcamps softening from 2021 to 2023 as we exited Covid, Coding Dojo was able to 3X revenue and get acquired.

These are 3 of the most surefire ways to grow revenue, even when market conditions are weak:

#1 Optimize for speed-to-lead → double-digit improvement in pipeline metrics

Tons of businesses take over 48 hours to call an inbound lead (if they call at all).

When we got that down to a few hours, that-alone drove a double-digit improvement in pipeline generated.

#2 Create a 'Qualified Opportunity' data feedback-loop into marketing

Red flag: Your demand gen team can't tell you the Cost per Qualified Opportunity" broken-out for each individual channel, campaign, and adgroup. That's a key difference between the growth engine of a Fiat vs. a BMW.

Example:

When we were managing-to Cost per Lead, we ignored the affiliate partner channel. Seemed like a small number of super-expensive leads.

But when we switched to looking at lower-funnel pipeline metrics (i.e. # of Qualified Opptys and Cost-per-Qualified Oppty), Affiliates was actually our most efficient channel.

It became a small but highly-reliable channel at 10% of revenue.

#3 Cold Lead Database: Drill, Baby Drill

Spicy take: you're probably not sending enough time-based offers/discounts. A lot of founders have anxiety about discounting, but even Nordstrom and Apple run sales twice a year.

(The way to protect your brand is to only share the discount offer with cold leads. Don't mention it on the website or to any current active pipeline).

These are the places I'd test an offer:

1. Email blasts - lowest effort, greatest reach

2. SMS - may not make sense in B2B, requires permission, slightly higher effort, but has much higher CTR than email

3. Retargeting -create audiences for past purchasers, cold opportunities, and cold leads. Retargeting ads can have conversion rates 10x higher than prospecting ads

I hope this helps! You can also read the full Coding Dojo case study (which includes 3 more growth tactics not covered here).

Onward!

-Prasid

When COVID-19 shut down cities overnight, local businesses faced a crisis that threatened their survival. For Nextdoor, the impact to the local advertising and offers business was immediate and severe. Fifty percent of local business vanished overnight, and the new SMB acquisition motion stalled.

In this conversation, Elena Luneva, former GM of Local Business at Nextdoor, shares how her team pivoted away from performance marketing to partnerships and PR, and shipped new products to meet the moment and support struggling merchants. She discusses the difficult decisions made, the lessons learned, and what she’s learned about adapting to a crisis.

Prasid: Can you set the stage: just before the crisis, what did Nextdoor look like? What was your role and focus?

Elena: At the time Nextdoor was a pre-IPO growth-stage company. I was the GM responsible for the local business vertical. And then, overnight, 50% of local businesses just shut down. Walking down Fillmore Street in San Francisco, seeing my favorites boarded-up, dim-lights, empty streets—it was devastating.

I was responsible for local business growth targets in the run-up to the IPO. But in a world where half the local businesses were shutting down overnight, we needed to completely rethink our approach—fast.

We had built our marketing strategy heavily around performance marketing, paid ads on Meta, and local outreach efforts. And suddenly, that playbook needed to be thrown out. Small businesses were in survival mode, and the usual conversion tactics—bringing them onto Nextdoor—weren’t viable.

Prasid: So let’s backtrack and share some more context on Nextdoor. My understanding is that initially, Nextdoor wasn’t focused on local businesses. It was focused on neighbor connection, supported by national advertisers.

Elena: Yes. We built the neighbor community product for years. What we started noticing in the data was that local businesses wanted to advertise—but initially, our system blocked these posts as spam. We realized there was a real need for local businesses to connect with neighbors, and an appetite for this connection from neighbors, if done tactfully. One thing I’ve learned in my career: when people start hacking your product, it’s a strong signal that there’s an unmet demand. If you can figure out how to make it valuable for the entire ecosystem, it can become a highly lucrative business line—and that’s exactly what happened with local businesses on Nextdoor.

I was hired to scale that local business line from 0 as the GM.

We built out an onboarding experience that allowed businesses to:

• Represent themselves on the platform

• Post directly in the neighborhood feed and engage with neighbors

• Create deals and promotions (e.g., “Buy your first coffee, get the second one free”)

As of the IPO, the local ads business had grown to 30% of Nextdoor’s revenue. Even more importantly, local businesses added value to the community: when neighbors engaged positively with businesses, they strengthened the whole ecosystem.

Prasid: Wow so the local merchant business unit was actually pretty built-out.

Prasid: So you mentioned 30% of the revenue is already coming from this new business unit. Let’s make sure we’re clear on where the other 70% was coming?

Elena: Our core business was selling ads to large enterprise brands that wanted to engage local communities—for example, home insurance companies, meal kit delivery services, CPG and other big brands.

But my business unit was more like Yelp on the local scale, trying to acquire local merchants and creating neighbor engagement products for them.

To acquire merchants we had a market-based approach similar to Lyft and Square, and were using performance marketing and feet-on-the-street direct outreach:

• Liquidity: Focus on getting merchant penetration within specific markets.

• Acquisition: Get businesses to create an organic business listing on the platform.

• Conversion: Convert those merchants through post, deal and neighborhood sponsorship products.

• ROAS (Return on Ad Spend): Optimize to generate paying merchants.

Prasid: Tell me more about the types of local engagement products you were building.

Elena: We tailored engagement products to the types of local merchants.

• For a coffee shop, as an example, local deals drove engagement.

• For a real estate agent, we introduced opportunities to “Sponsor a Neighborhood” and appear in the real estate map and various placements in the feed.

• For plumbers we introduced a post type to showcase their projects.

One of our biggest product marketing challenges was positioning the ad products for an SMB buyer. Small businesses don’t think in terms of CAC; they think in terms of their craft and community connection. So we couldn’t just say “lower CAC.” Instead, we had to frame it in words and outcomes relevant to the local business, for example: “Get access to 3,000 neighbors in Larkspur and Tiburon.”

To maintain a balance between supply and demand, we launched one market at a time. For example, for the deals product to have perceived value, a neighborhood “Deals” page would need at least 10 active deals listed.

Prasid: How many markets were you in at this point?

Elena: We were already nationwide.

The COVID-19 Crisis: A Need to Pivot

Prasid: Great so now we have some background on the two business units, and what products and acquisition channels your Local Business unit was leveraging. Now let’s go back to when the crisis hit. You described walking down Fillmore Street and seeing the boarded-up storefronts. Take us into that moment—what was going through your mind as a leader responsible for local business growth? How did you balance the emotional weight of seeing businesses struggle with the need to quickly pivot strategy?

Elena: It was heartbreaking. On one hand, the board understood what was happening—we were in a crisis, and no one expected business as usual. But on the other hand, there were still numbers to hit, revenue expectations to meet and a business to run.

But it wasn’t just about lost revenue, it was about people’s livelihoods and how they could support their families. It was about the loss of everyday creature comforts—the spot where people grabbed lunch, shops that had been there for years and a key part of what made my neighborhood what it was. And we had to ask ourselves: How do we help these businesses survive? What role could Nextdoor play in keeping communities thriving during this time? And that was the perspective I took on as a leader. How can I help?

Up to that point we’d been focused on acquisition: boots-on-the-ground sales teams, pushing businesses to tip a neighborhood by getting a critical mass onto the platform. As COVID-19 hit we couldn’t send people out on the street. And we couldn’t keep pouring money into performance marketing, conversion rates were tanking. We unexpectedly hit the flatline of the conversion curve, it just fell off a cliff.

So we made three changes:

• We paused performance marketing to preserve capital.

• We shifted from a sales-led approach to partnerships and PR.

• We pivoted our local business team to launch a local business bundle, giving local businesses tools to survive.

The New Strategy: Supporting Local Businesses

Prasid: Walk us through the solution you implemented. What exactly did you do, and who was involved?

Elena: We completely pivoted our product roadmap. Our goal was to get money into the pockets of the remaining local businesses right now, even if they couldn’t physically open or adjust how they did business. One way to do that was gift cards.

The idea was simple: give customers a way to support their favorite local businesses today, and redeem later when things reopen. Another solution was to help dine-in restaurants pivot to offering delivery.

So we built a business bundle that allowed local merchants to:

• Add gift card, delivery, and donation links to their profiles.

• Easily integrate with DoorDash, Uber Eats, GoFundMe, and OpenTable.

• Pause advertising payments for existing merchant subscribers if they needed financial relief.

We also changed our GTM strategy. Instead of trying to acquire businesses one-by-one through sales, we leveraged partnerships. And we used PR to amplify the message.

We leaned into touchless delivery and fast-casual dining, knowing that consumer behavior was shifting toward safety and convenience.

Prasid: A lot of online platforms (e-commerce, stock trading, etc.) saw a huge surge in consumer traffic during COVID-19. Did you experience that?

Elena: Yes—there was huge growth in neighbor engagement. Nextdoor became the go-to platform for how communities stayed connected.

One of our other business unit’s key investments was in the Help Map, which allowed neighbors to volunteer to help each other—whether that meant picking up groceries, delivering medicine, or running essential errands for someone who couldn’t leave their home.

We grew to be in 1 out of every 3 households—that gave us an opportunity to become the local channel for information and support.

Not every business was able to use or wanted to use existing delivery and fundraising platforms like GoFundMe, Uber Eats, or Treat, so we had to find ways to bridge the gap.

Prasid: How did you get businesses to opt in? How did you pre-populate these features for them?

Elena: Normally, these kinds of tools would be part of a paid ad product—but we made them free.

We templatized everything—creating a simple, seamless way for businesses to add gift card options, delivery links, and donation requests to their profiles.

But there was still something missing—the right partnerships to fully connect the experience. We had the infrastructure, but we needed external platforms to complete the loop and ensure businesses could easily integrate with existing payment and delivery systems.

The Role of PR & Partnerships

Prasid: Since you pivoted away from performance marketing, what role did PR play in getting the word out? Were there specific campaigns or media strategies that helped amplify this initiative?

Elena: Performance marketing wasn’t viable anymore—RoAS was dropping, and businesses were pulling back on ad spend. We needed to preserve capital, but we also had to find a way to support businesses in real time. We saw a clear shift in business needs—restaurants couldn’t allow dine-in customers, so they pivoted to delivery and touchless dining options. At the same time, many businesses needed direct financial support, so platforms like GoFundMe became crucial.

Nextdoor already had a presence in one out of every four households, so our role became connecting businesses with neighbors. We added new functionality to enable businesses to add a GoFundMe donation link in their profile description and help restaurants transition to delivery by partnering with Uber Eats and similar platforms. And if they were already listed on those platforms, we offered businesses the option to opt-in to featuring those adjusted capabilities.

Once these features were live, PR became a critical channel for driving awareness. We focused on human-centric stories starring small businesses persevering through COVID, adjusting their strategy to survive, and built a three-pronged announcement strategy:

1. Community announcements on the Nextdoor platform to engage neighbors.

2. Press releases and media outreach to amplify how we were supporting businesses.

3. Joint announcements with delivery and fundraising partners to expand reach and credibility.

This approach ensured businesses actually knew these tools were available and could start using them immediately to stay afloat.

Prasid: That’s so interesting. Was there money changing hands in these partnerships? It sounds like a great distribution channel for Uber Eats.

Elena: No, I don’t believe any money was changing hands between Nextdoor and Uber Eats.

The way it worked was:

1. Nextdoor integrated with Uber Eats, allowing small businesses to add an “Order Delivery” or “Buy a Gift Card” button to their profiles.

2. Merchants on Nextdoor could enable these options, making it easier for customers to support them.

3. Neighbors browsing Nextdoor would see these new options—allowing them to order directly from a small business or purchase a gift card, powered by Uber Eats or engage with donation links powered by GoFundMe.

For businesses already on Nextdoor, we could pre-populate their profiles with these features. For businesses not yet on the platform, it was an easy on-ramp—they’d join and immediately benefit from the visibility of the joint campaign.

While it was a valuable partnership for all sides, I don’t believe there was direct revenue-sharing or payments between Nextdoor and partners—this was more about expanding reach and driving engagement together in support of local businesses.

This was in stark contrast to Yelp, which also introduced donation links for small businesses during the pandemic—but with one key difference: they didn’t notify businesses or give them a choice to opt out.

When Nextdoor launched the functionality to help businesses offer delivery and gift cards, we didn’t just turn it on and assume everyone would want it. Instead, we:

• Talked with businesses first

• Proactively informed businesses about the new feature

• Allowed them to opt in, rather than being automatically enrolled

By giving businesses control, Nextdoor built stronger long-term engagement and trust, ensuring businesses felt like partners, not just users on a platform.

Prasid: What role did PR play? How did you use storytelling to amplify this initiative?

Elena: We leaned into local storytelling. One moment that stood out—I took a picture of my daughter getting ice cream delivered from Fillmore Creamery. That small, everyday experience, that became such a luxury. I can still see her smile in my mind. That’s exactly what we were fighting to preserve—the moment of happiness that local businesses bring.

So PR focused heavily on local news outlets and individual business stories. Our team worked closely with employees and neighbors, listening for specific local narratives that resonated with communities.

A big part of this was social listening—we had a team dedicated to surfacing the most compelling stories and making sure they got in front of the right media outlets.

At the end of the day, we weren’t just another platform—we were the local social network. That positioning helped us rally communities and get real traction and money into local business pockets when they needed help from their neighbors most.

Navigating Internal Challenges

Prasid: Partnerships were a key part of this pivot. How did you make this happen so quickly?

Elena: A lot of it came down to relationships. Adel Farahmand was instrumental in making sure we had the right partnerships in place. As a GM, you have to ensure both R&D and GTM are hand-in-glove rather than tossing things over the fence—it’s not just about building a product but also making sure it actually reaches the businesses that need it.

We initially explored working with OpenTable, but the integration proved challenging. The focus for OpenTable was high-end restaurants and it took time for many of them to pivot to delivery. So we had to pivot and find partners that could move faster from a technology and API perspective.

Prasid: Tell us more about the org structure. Were advertising, partnerships, and PR part of your team, or did you have to work cross-functionally? If they were outside teams, how did you navigate internally to get their focus on this initiative?

Elena: Execution was spread across multiple teams under the broader marketing org with a dotted line to EPD (Engineering, Product and Design) so we really had to work cross-functionally.

Zooming-out, this pivot required a company-wide strategic decision—do we divert resources toward a crisis response, or do we stay the course?

We had three possible paths:

1. Continue as-is – Stick to the original plan, even though businesses were shutting down.

2. Do nothing – Turn off marketing spend entirely, preserve capital, and shift our focus away from small businesses toward large advertisers.

3. Do something for small-businesses – Invest in supporting local businesses, even though it was an unknown bet. The thinking being that if these businesses survived, they’d become long-term customers.

We chose #3—but that required getting alignment across Product, Finance, Operations, and Marketing.

Prasid: You were pivoting and shipping fast. How did you get alignment across teams?

Elena: Alignment was critical. This wasn’t just a marketing challenge; it was a cross-functional shift that required buy-in from Product, Finance, Operations, and GTM teams.

The key was clear decision-making frameworks and rapid scenario planning. We didn’t have months to figure this out—we needed to move yesterday.

Prasid: What were the guiding principles in making these calls?

Elena: We had to ask:

• What are we modeling? Are we optimizing for short-term revenue or long-term engagement?

• What’s the role of Product? Just because we could build something didn’t mean we should—every feature had financial implications.

• What do we stand for? Do the values we have as a company mean something?

Prasid: How did you communicate this shift to stakeholders, investors, and the team? Did you face any hesitations or pushback?

Elena: The biggest challenge was navigating uncertainty. We were making a big bet on local businesses at a time when 50% had already shut down, and more were projected to, indefinitely. Internally, stakeholders were asking:

• Why not focus on enterprise customers instead?

• Should we just preserve capital and wait?

• How do we know this pivot will work?

We had to frame the decision in clear, logical terms—showing both the risk and the opportunity.

To get buy-in, we modeled multiple financial scenarios—best-case, worst-case, and middle-ground projections. We also had to ensure cross-functional alignment, especially with finance and operations.

Instead of focusing on immediate revenue, we prioritized customer retention and support—keeping businesses engaged with Nextdoor and focusing on trust, so they would choose to work with us as conditions improved.

This shift wasn’t just about survival; it was about long-term positioning and how we wanted to show up—helping businesses weather the storm so they’d trust and invest in Nextdoor when they were ready. We were in it together.

Results & Lessons Learned

Prasid: Looking back at this initiative, what were the biggest takeaways? What impact did this strategy have—not just on revenue, but on how businesses engaged with Nextdoor in the long run?

Elena: We stemmed the exodus of businesses from our platform and positioned Nextdoor as a trusted pro-local business brand. The strategy delivered meaningful results in several ways:

• Prevented mass attrition – Helped retain businesses on the platform even when they couldn’t afford advertising.

• Strengthened brand positioning – Nextdoor became the local platform that supported businesses when they needed it most.

• Met urgent customer needs – Provided an immediate, tangible solution during a crisis.

• Maintained long-term relationships – By allowing businesses to pause subscriptions while still benefiting from the platform, we ensured they stayed engaged for the long run and turned to us first when things improved.

This wasn’t just about revenue—it was about trust and long-term relationships. Businesses remembered who showed up for them in a crisis, and that mattered when the market started to bounce back.

Prasid: In hindsight, what worked best and what didn’t? What were the key takeaways from this experience?

Elena:

• What worked:

  • Partnerships let us scale without huge acquisition costs.

  • PR drove massive organic engagement.

  • Giving businesses control helped build long-term trust.

• What didn’t work as well:

  • Some integrations, like OpenTable, never materialized for delivery since high-end restaurants weren’t structured for takeout.

  • Adoption of gift cards took longer than expected—people weren’t used to buying them online.

Prasid: If you could focus your Product and Engineering teams on something else, what might you have done instead?

Elena: I think we should have prioritized two things:

1. Expanding the Help Map – As a reminder this was a map where neighbors could raise their hand when they needed help, and other neighbors could volunteer to help them. For example someone immuno-compromised needed help picking up groceries. This feature had incredible organic traction. Had we focused on scaling it earlier, we could have driven more scaled and immediate impact to communities.

2. Building a resource center for business owners – A centralized hub with grants, government aid, and practical survival tools might have been more valuable than direct giving from neighbors.

Ultimately, this experience reinforced a key lesson: Sticking to the company values, doing what’s right for your customers is always the right solution, the revenue will follow.

Final Thoughts

Prasid: You’ve talked about how this experience shaped your perspective on GTM strategy. I know you also have taught growth and product management with both Reforge and Maven. How did going through this crisis inform your course?

Elena: This crisis reinforced something I had learned over 20 years in product leadership: GTM matters as much as the product itself. A lot of PMs operate with the “if we build it, they will come” mindset—but that’s rarely how things actually work. Aligning PM+GTM into a partnership ensures that the company builds the right products that customers buy that move the business forward.

My upcoming course Go-to-Market Strategy for Product Leaders focuses on four areas:

1. Go-To-Market Strategy – Understanding ICP (Ideal Customer Profile), positioning, and reaching buyers effectively.

2. Financial Acumen – How to model metrics, talk about product impact in a way that your CFO understands, and ensure pricing and revenue models make sense.

3. Executive Presence & Storytelling – How to frame key product metrics in a compelling way to drive alignment across leadership.

4. Growth Engine & AI Leverage – How to use AI to automate and streamline GTM communication, making messaging to stakeholders more effective.

The course is built around real-world case studies, including deep dives into successful execution in the four key leadership areas.

Prasid: If other startups face a similar crisis in the future, what key learnings would you share?

Elena: This experience shaped how I think about growth and marketing in a crisis.

• Throw out the playbook when needed. Pivot fast—sometimes the only way forward is a completely new strategy. We moved from a sales-heavy model to a partnership-led one almost overnight.

• Leverage partnerships over direct acquisition. Instead of costly performance marketing, we scaled through strategic alliances.

• Empower businesses, don’t force them. Unlike Yelp’s auto-enrollment, we let businesses opt in, which builds long-term trust.

• Prioritize immediate customer needs. Businesses didn’t need a SaaS tool; they needed cash flow. Suspending subscriptions and ad spend kept them engaged for the long haul.

At the end of the day, companies that put their customers first and adapt quickly will build the strongest relationships—and that’s what sustains a business beyond the crisis.

Elena Luneva is a Product, GTM and AI practitioner, with over 20 years in product leadership roles at GoFundMe, Braintrust, Nextdoor, LiquidSpace, OpenTable and BlackRock. She advises companies and teaches PMs to become impactful business leaders. Follow her writing on Substack and learn the skills that advance your career in the PM -> G(T)M course on Maven this April. Follow Elena on LinkedIn and read more of her insights on Substack.

This bonus post is a bit different—I wanted to share a little “Drip Series Zap” I built using Zapier to help Substack authors add a drip series to their content engine.

The problem:

Our Substack had just crossed 1,500 subscribers (and growth is actually accelerating). The Substack is meant to be a lead gen tool for our consulting business. But there’s zero mention of the consulting business in our content.

The solution:

Like any good CMO, I wanted to create a drip series so when new folks subscribe, the first 2-3 emails orient them on what we do and how we can help, in-between all the [hopefully] high-value content.

The wrinkle:

Turns out Substack provides no way to send a drip series. Just a single welcome email.

And, because they I guess they hate RevOps people (like me), they don’t have a public API or an integration with tools like Zapier, Mailchimp, etc.

The solution:

I’d have to hack something.

I found other people online who had figured out a hack.

I ended up spending like 2 hours banging my head before getting it done.

Here’s what I put together, with screenshots, so you can hopefully do this in like less than 20 minutes.

Here are the steps summarized:

1. Create a Gmail Label / Filter

2. Create a Zap and Use that Filter as the Trigger

3. Add a “Formatter” Step to Extract the Email Address

4. [Optional]You can choose to store all subscribers in a Google Sheet.

5. Add a “Delay” Step

6. Create “Send Email” Step

7. Repeat the Delay and Email Steps for Drip #3 and beyond

If you think this could be helpful to you, read on.

1. Create a Gmail Label / Filter

I found this method cleaner/more reliable than implementing search filters inside Zapier itself.

Make sure to save the filter by hitting “Create filter” and then saving it as a “Label” (argh, Gmail confusing feature-naming 🤷🏽).

Here’s the filter I created:

2. Create a Zap and Use that Filter as the Trigger

You can see the entire flow below, but the main thing to pay attention to is the configuration:

• Set Trigger = New Labeled Email

• Connect Your Gmail Account

• Set Configuration to whatever you named your Label/Filter

3. Add a “Formatter” Step to Extract the Email Address

Turns out that with Zapier’s AI functionality this was easy to figure out.

I asked and it pointed me toward the “Formatter” and suggested a function called “Extract email.”

Wowza.

For the input, look for a field named “Body Plain.”

4. [Optional]You can choose to store all subscribers in a Google Sheet.

I wanted to do this so I could turn on the zap and see exactly what emails were being extracted before I actually added a “Send Email” step.

5. Add a “Delay” Step

Since Substack has a built-in welcome email, I only need Zapier to send Emails #2 and #3 in my Email Drip Series. So I added a 2-day delay between a New Subscription and the first Zapier-powered Email-send.

There are a couple different types of delays. I chose “Delay for” and chose 2 days.

6. Create “Send Email” Step

You’ll notice I haven’t actually taken the time to drop-in a well-formatted email yet. I’m not 100% sure how reliable Zapier’s HTML email capability will end-up being. If so I’ll come back and update here.

7. Repeat the Delay and Email Steps for Drip #3 and beyond

You’ll notice I haven’t actually taken the time to drop-in a well-formatted email yet. I’m not 100% sure how reliable Zapier’s HTML email capability will end-up being. If so I’ll come back and update here.

Voila!

As startups scale from 50 to 100 to 500 people, cracks in their operating systems often emerge. For much of the past decade startups could keep growth steady by paving-over the fault lines that emerged with venture capital dollars. They’d buy customers with promos (Postmates, Uber) resulting in poor CAC to LTV ratios. Or they’d throw bodies at the problem, hiring vast sales teams (Carta, Toast). As we’ve seen with significant recent layoffs, that’s no longer an option.

So how do you grow when capital will be more constrained? How do you prevent these fault lines from forming in the first place? I’ve been a full-time head-of-marketing for 5 startups and an in-the-weeds-advisor to 4 growth stage CEOs, which means I’ve had plenty of chances to get this wrong, and this post will help you leapfrog the growing pains I’ve experienced. This post will help you design your company’s goals, organizational structure, and planning processes to prevent fault lines and promote speed. Here are the six rules we’ll cover:

• Rule #1: Get your whole organization aligned on the growth model and the levers that drive growth

• Rule #2: Organize squads around each lever, and pick thoughtful north star metrics to measure each squad

• Rule #3: Actively deprioritize: make it clear what you’re okay missing and what fires should be left to burn in order to hit the north star metrics

• Rule #4: Avoid HiPPOs. Create a quantitative, rational framework for evaluating which projects get us the most leverage on each key metric

• Rule #5: Sub-divide into cross-functional two-pizza teams; too much collaboration can slow teams down

• Rule #6: Let squads stay-the-course for multiple quarters (at least) so they can build domain expertise and pick up speed

And what better way for me to illustrate these 6 rules than by sharing six mistakes I’ve made leading growth teams. Tally ho!

Mistake #1: Team Isn’t Aligned on What the Key Growth Levers Are

It was my second week as head of marketing at a growth stage startup. We were at an annual planning leadership offsite, and my CEO wanted to establish customer targets for the year (totally reasonable). He’d asked our consultant-VP-of-Finance to do a first pass. The approach went something like this: “Based on our growth rate the past two years, this year we plan to grow customers by 20% every month.” He laid out the historical data, adjusted for seasonality, and laid out the coming year’s targets. Everyone nodded their heads: this seemed like a data-driven approach. And the rest of the leadership team thought in terms of projects shipped or people hired, not in terms of levers pulled.

The trouble with that approach is that Customers is a lagging indicator. And looking at customer growth in isolation overlooks the leading indicators or drivers of customer growth. In our. case, those leading indicators included incredibly strong category growth which had driven organic leads, giving our business significant tailwinds. I felt that we ought to build a different model. But, hoping to seem agreeable, and hungry to deliver on these ambitious goals, I went along.

That was my failure: I was so new that I hadn’t had a chance to build a proper model, and I was too inexperienced to go with my gut and advocate for a different approach. A few months later I did build a proper model. It showed category growth and organic lead growth were slowing, and we’d likely miss our targets. I had to go back to the board the next quarter and re-state our growth targets downward. Not a good look for the new Head of Marketing. Yeesh.

What I’ve learned is that it’s incredibly important to boil the business down into growth levers, build the model, and educate the exec team (one-by-one if you have to). For a SaaS business like ours, we distilled the business down to these key levers:

• Organic Leads

• Marketing Spend

• Cost per (Paid) Lead

• Lead > Subscriber Conversion rate

• Churn rate

The way I really drove-home the levers was by creating a better model: one that showed how moving each lever changed our customer growth trajectory. Here’s a simple model you’re welcome to copy that may translate well to your business. I found that a more complex version with cohorting was of course more helpful for the growth team, but actually less-helpful for teaching and demoing with the exec team.

Now, going back to our VP of Finance from earlier who planned to grow customers 20% MoM. With this model in hand, I was able to illustrate how that might happen. In this model, there are 4 levers we can pull to grow Customers by 20%:

1. Increase budget by 20%

2. Ship a 20% improvement in Cost per Lead (ex: landing page improvement that converts 20% higher)

3. Ship a 20% improvement in Lead > Subscriber conversion rate (ex: checkout page that converts 20% higher)

4. Ship a 20% improvement in Monthly Churn rate (ex: onboarding experience that retains 20% longer)

To sustain 20% MoM customer growth, we’d need to ship one initiative like this every… single… month. Once our department heads grokked that, it gave us so much clarity. And it fueled a sense of urgency. Now we could work backwards, mapping initiatives to months to outcomes. The next two years we grew revenue by roughly 6X.

Mistake #2: Teams Are Not Organized Around the Right North Star Metrics

Picking the right north star metric is incredibly powerful. Facebook’s early growth team decided their key lever would be engagement, and famously chose 7 friends in 10 days as their north star metric. What’s often overlooked in that story is that they chose to 7 friends in 10 days over the more prevalent MAU and DAU metrics that competitors were using to measure engagement. They did this because they believed 7 Friends in 10 Days would be a more actionable north star metric for the team. Aside: To make this post a drinking game, take a sip every time I say “north star metric.”

When I joined a recent startup, our sales manager was measuring his team on meetings booked and dials per day. Sales ops was measured on keeping the sales team happy. Our email marketer measured herself on open rates and click-through-rates. And our Director of Marketing was measuring her agency on cost-per-click and leads.

These metrics are convenient, which is why we so often reach for them. But they are are also siloed. They’re too narrow. After all, who cares if open rates are off the chart if the Leads don’t convert to Opportunities? A growth squad, like the Avengers, is a cross-functional team that comes together to fight the biggest baddies, the ones too strong for any one to beat alone. And we need metrics to match.

So the biggest change I made was to set up a cross-functional growth squad that were each organized around moving one key lever. We were spending mid-six-figures every month on paid search and paid social and we had just brought-on a strong agency to manage it, so the first growth squad we had the capacity to spin up was a “Leads Squad.” But the key is how we chose to measure them.

We considered a north star metric of total Leads but this was too loose - we’d have no sense of the lead quality. Our product team was working on a new qualification engine which would enable us to measure Product Qualified Leads (PQLs), but it was still 4 months from shipping. We needed a quality-signal we could measure today, so we chose to go down to the SQL level.

At first the Leads squad, especially Phil our excellent agency lead, pushed-back: the sales team can fudge who they converted to SQL, which puts us completely at their mercy. The counter-argument is that the sales team is measured on Customers regardless of how qualified leads are, which puts them totally at marketing’s mercy. This shared-accountability was a bet, but one that paid off handsomely.

The other variable at play was budget: if we increased budget, they’d inherently deliver more SQLs. I wanted a metric that isolated the squad’s contribution from budget increases, so I chose the north star metric of Cost per SQL.

Over the course of the next four months, our cross-functional Leads squad, aimed at it’s Cost per SQL north star, surfaced unlikely problems and creative solutions:

• The agency noticed Cost per SQL was 20% worse on weekends when we had few sales people working, so we staffed up on weekends and closed the gap.

• Our target customers are suburbs so we were excluding rural and urban zipcodes at the ad level, but discovered Paid Search leads were being disqualified before the SQL stage because of geography. When we dug-in, the team discovered Google’s zipcode-based targeting wasn’t as accurate as Facebook’s, and switched Google to targeting by city radii instead.

• We knew that our connection time from inbound lead to call was averaging days, and wanted to bring that down to hours, so our sales ops manager Aaron and marketing ops manager Johnna delivered project after project to bring that connect time down to hours.

By my sixth month mark at the startup (and our growth squad’s fourth month in existence), we’d managed to double our mid-six-figure spend while simultaneously reducing CAC.

Mistake #3: Leaders Don’t Actively Depriorize

When you’re changing how teams are managed and measured, there can be a tendency to keep stacking new “top priorities” on top of one another. What’s important is that you also make it clear what it’s okay to stop doing.

As a leader, it’s important you also actively depriortize. I loved this Masters of Scale interview where General Stanley McChrystal said:

The real courage in a leader is not in telling people what to do. It's telling them what it's okay not to do, because there's a whole bunch of other things that they kind of think they should do and the leader has to sign up and say, "If you don't do any of these, I'm okay with that, as long as you do these things that really matter.

I once worked with a consumer SaaS business where 90% of our customers churned with the first year. I was also aware that our top of funnel SEO advantage, which had sustained our acquisition growth for years, was starting to lose ground to competitors. I banged on the table in department heads meetings, explaining that we urgently needed to implement SEO fixes, but with such a small engineering team, there were always too many competing priorities, the team was unfocused trying to solve acquisition, conversion, and retention, all at once, and we weren’t making substantial gains on any front.

The mistake I made is that with such a large leak in the bottom of our funnel, I should have said it’s okay to fail at acquisition as long as we succeed at retention. The model I later built showed quite clearly that if we doubled acquisition, the business would double within 4 months, and then plateau once again. We needed to let the acquisition fire burn and focus putting out the retention fire.

Mistake #4: No Framework for Prioritizing Projects Rationally

I see two things happen pretty often with growth teams. First, when growth teams are staffed by folks who are new to growth, they sometimes gravitate toward shiny objects, like a SaaS company launching a referral program or a contest. Second, the decision on what to pursue ends up being governed by HiPPOs, which I recently and delightfully discovered refers to “Highest Paid Person’s Opinion.” The solution is the same: a prioritization framework rooted in math and experiment data.

Let’s take our simple growth model above. Let’s say our growth squad is focused on improving the MQL > Opportunity lever. They might brainstorm many projects to move that lever. The goal is to use historical experiment results and the team’s experience to estimate the level of effort and impact of each idea. Then we prioritize the ideas that are the highest leverage, meaning they achieve the highest impact at the lowest effort. This framework has been floating around for years, but here’s my personal Growth Playbook Template.

Mistake #5: Org Structure Slows-Down Execution

Jeff Bezos made famous the idea of 1-way and 2-way doors. His thesis: if the decision is reversible, reduce decision-making rigor and prioritize speed. Similarly, Netflix made famous a hiring approach to hire the highest quality talent and empower them with fewer layers of oversight and rules. The thesis: great people self correct, so reduce oversight and prioritize speed.

Similarly, I would argue organizational design is a tool we can use to promote speed, rather than retard it. Let me share an example that will likely sound familiar: when Bloc was small, I’d grab the nearest engineer and ask for help doing whatever needed doing. As the company scaled, our first PM suggested a weekly planning meeting where stakeholders could come together, discuss project priorities, and decide what to tackle.

The team grew further: now we had the Heads of Customer Success, Design, Marketing, the COO, both founders, and a handful of stakeholders from individual teams all lobbying, every week, to get their engineering tasks prioritized. We wanted to be data-driven, so stakeholders were encouraged to bring data. On numerous occasions me or my directs would spend hours prepping charts and graphs for the meeting, when completing the engineering work itself would’ve taken 30 minutes. The problem looked similar at SoFi and Rafter before that, and similar at Codecademy afterward. The solution, it turns out, is another of Bezos’s greatest hits: the two-pizza team.

As soon as a startup scales to the point where you have many stakeholders chasing engineering priorities, it’s time to sub-divide into squads. Others have done a fine job of documenting the data backing-up two-pizza teams but Bezos sums it up well:

“Communication is a sign of dysfunction. It means people aren’t working together in a close, organic way. We should be trying to figure out a way for teams to communicate less with each other, not more.”

The more nodes we have in the team, the more coordination is required. When the nodes have competing north star Metrics, thrash increases, and throughput declines dramatically.

So how should you organize your two pizza teams?

Around your North Star metrics of course!

Depending on the North Star metric, the cross-disciplinary talents you need on each squad will vary. In Kieran Flanagan and Scott Tousley’s Growth TL;DR interview, Calendly’s VP of Product Oji Udezue says Calendly added representatives from Product Marketing and Customer Support to every squad within the company. (Sidenote: I listen to tons of podcasts. Growth TL;DR has been the most consistently helpful as a startup marketing operator!)

For the example above, I can imagine stakeholders across both marketing and product working together on a top of funnel growth squad whose North Star metric is growing MQLs per month, while a second squad with Product and Customer Support folks might join a Customer Retention squad whose North Star metric is Month 1 NPS.

Mistake #6: Reorganizing Squad Members and North Star Metrics Too Frequently

You’re likely familiar with the life-changing magic of OKRs. Codecademy had an incredibly talented team and worked hard to be the best-run startup possible. As we scaled past 75 people, we started involving the whole organization in OKR planning. The leadership team set company goals, then each department set goals, then each individual. This meant spending a week meeting and planning, then another week aligning across teams. Squad assignments needed to get adjusted, and squads might be merged or split in two. And before we knew it, the process was taking 3 weeks, leaving just 9 weeks per quarter to execute. Once plans were settled, it would take time for teams to build-up context before they could start shipping. And just as the team was starting to pick up momentum, the quarter ended, and the process started over! Blast!

Our mistakes were twofold:

• First, our goals were shifting too aggressively each quarter. It’s healthy to grade and tweak OKRs quarterly, but changing key levers entirely or forming new squads should not be happening once every twelve weeks. By doing that we were crushing the team’s momentum just as they hit their stride.

• Second, we were sensitive to team members who wanted to rotate rather than being pidgeon-holed into one area of the business. Engineers were attracted to obscure technical challenges rather than the levers that really drove the business. Designers glorified product design rather than conversion optimization. And as a mission-driven freemium education startup, folks across the board were keen to work on the free courses, but uncomfortable thinking about paid conversion.

One solution is to make growth squads permanent. Calendly’s Oji Udezue argues there are speed benefits that come from engineers with specialized domains, and designers can leverage hundreds of hours spent interviewing a single customer persona to solve problems faster and better. The added upshot of making squads permanent at a mission-driven startup is that candidates know the team they’ll be working on before they join, so when you hire a growth designer or growth-engineer, they go in fully-aware they’ll be working on growth.

Conclusion

Now more than ever we need to build growth into our operating systems: our goals, processes, and organizational structures. When we do this right, we unlock enormous speed, achieve a greater business impact, and ultimately build sustainable organizations that will leave a lasting impact on our world. Here are six rules one more time:

• Rule #1: Get your whole organization aligned on the model and the levers that drive success

• Rule #2: Organize teams around each lever, and choose north star metrics that’s are broad leading indicators rather than narrow siloed metrics

• Rule #3: Actively de-prioritize: help your team focus on the north star metric by making it explicit that it’s okay to fail or delay other things

• Rule #4: Fight the HiPPOs! Create a quantitative, rational framework for evaluating projects, and weight them by the leverage gained

• Rule #5: Too much collaboration can make teams slower. Set your team free by sub-dividing into cross-functional two-pizza teams

• Rule #6: Let your squads stay the course for multiple quarters or years so they can build domain expertise and move faster

I hope these mistakes were as helpful to learn from as they were rough to re-live.

Prasid Pathak is a 3-time CMO and 2-time CRO, specializing in building high-performing revenue engines. As a revenue architect, he helps companies optimize their go-to-market strategy and drive scalable growth. With a proven methodology that has consistently helped businesses increase revenue by +20% and +50%,

Prasid works with teams to ship iteratively and deliver results. Follow him on LinkedIn or learn more about his agency Airframe Labs. If you’re looking to transform your business, feel free to get in touch.

That’s why I’m super-excited that today’s post showcases our new operating model: the fractional growth team.

This was our third time using this model to help a founder go-to-market and build a high-performing revenue engine. If you need help scaling your business, feel free to get in touch.

Vinu Natarajan, founder and CEO of Consolidate Health, had spent the past year assembling a team of product, design, and engineering folks, and had been building an app to help patients and doctors manage medical records.

They were almost ready to go-to-market.

Normally, Vinu would have hired a head of marketing, and would have started building out a growth team.

Next, they would have started evaluating tools, buying them, and stitching them together.

And finally, they would have needed to measure their impact, and would have probably relied on a CTO or Head of Data Science to build data pipelines and dashboards.

Except Vinu didn’t have time for any of that. He needed to show traction, fast.

So he accelerated the GTM journey by hiring us to be his fractional growth team.

As Vinu put it:

“Airframe’s team helped us ship faster and achieve traction faster. By showing us how to implement tools like Intercom and PostHog, they let our core engineering team stay focused on the product.”

We operated exactly as an in-house team would:

• We had Consolidate Health emails, we were on Slack, you could book our calendars

• Unlike an agency, there was no predefined “scope of work:” we’d work on any problem, any tool, any challenge, to get the job done

• And unlike most agencies I’ve worked with, we were the ones driving meetings, driving projects, driving results, and pushing to go faster

And unlike most in-house growth teams, we’d done all of this before. In fact, this was my 7th time running a zero-to-one go-to-market like this. And I was going to make sure it was our best one yet.

Do you want to hire Prasid & Airframe Labs? We’ve helped YC-backed startups like Scribd, scale-ups like Booksy, and Fortune 500 companies like SiriusXM. In every case, we’ve helped them grow revenue, fast. And we can do the same for you.

Work with Prasid

Challenge #1: Choosing the Right GTM Strategy for a Marketplace Startup

When Vinu first approached us, the original plan was a Direct-to-Consumer (DTC) go-to-market where we would get tens of thousands of patients using the app, and then would approach the other side of the marketplace: clinical researchers.

So my first step upon joining was to build a model for Vinu. This exercise uncovered two critical obstacles:

1. DTC Acquisition costs would be quite high: The cost to acquire a healthcare patient through digital channels varied depending on the specific channel and type of healthcare practice. Here are some average patient acquisition costs for digital channels:

• Paid Search (PPC): $342

• Meta Ads: $577

While those types of acquisition costs could have made sense when you’re selling a paid product, they didn’t make sense for Consolidate Health’s free-to-use patient tool.

2. Traditional online acquisition channels were too blunt

Consolidate Health’s model required a critical mass of patients with the same disease in order to match them with research studies.

But there weren’t great ways to target people in specific diseases with online ads.

So to get a critical mass of 1000 patients with the same disease, we might have had to acquire 100,000 patients.

The Pivot: A B2B2C Approach That Scaled

Instead of chasing patients one by one, we proposed a B2B2C model. What if we provided a free tool for doctors to manage their patients’ data? By reframing the audience from patients to providers (i.e. Doctors offices), we could acquire patients for free. And by targeting doctors with a specific speciality, we would reach our critical mass of patients much sooner.

Challenge #2: Shipping v1 of the GTM Engine

At Consolidate Health, the team’s instinct was to build—a natural reflex for a team with deep product experience at larger companies.

Because we had tremendous zero-to-one startup experience, we were able to guide the founding team toward a different approach: conserve engineering resources for core product. For the rest, leverage off-the-shelf parts. This approach helped them ship faster, and reduced time-to-value.

Overview of our Revenue Tools Stack

1. ActiveCampaign: This HIPAA-certified marketing automation tool saved Consolidate Health at least $10K annually compared to Salesforce. It offered the functionality they needed—campaign automation, patient communication, and provider engagement—without unnecessary overhead.

2. RudderStack: Integrated data streams across the patient and provider journey, reducing manual data wrangling and freeing up engineering hours.

3. Intercom: Provided live chat, in-product notifications, and ticketing capabilities—essential for optimizing patient engagement and activation rates.

4. PostHog: Delivered granular product analytics. The auto-tagging and self-serve tagging functionality meant that we didn’t need the engineering team to code conversion events manually. Our team could create events ourselves, and build all the dashboards the marketing and product team’s needed.

By adopting this build-vs-buy philosophy, we accelerated CH’s time-to-value while keeping their core engineering team focused on what mattered: the product.

Challenge #3: Choosing A Marketing Automation Tool Juggling Privacy, Compliance, and Other Landmines

Healthcare isn’t like other industries. So for Consolidate Health, privacy wasn’t just a checkbox; it was critical. We needed to find tools that were economical but also HIPAA-compliant.

We demoed multiple platforms, including Salesforce, HubSpot, Paubox, and Iterable, to find the right fit.

Salesforce: We had seen a ton of startups lock themselves into Salesforce because they thought “they should.” The reality was that today the time-to-value and maintenance costs for Salesforce were much higher than alternatives.

And once you chose a CRM, you almost never migrated away. So we were able to dismiss Salesforce fairly early in the investigation.

Hubspot: Hubspot was my favorite of the bunch, but it was about as expensive as Salesforce, making it too expensive for where Consolidate Health was in their journey.

Paubox: Paubox was the only vendor we looked at that marketed itself as being healthcare-specific. When demoing Paubox, we asked if they had an integration with other tools we were using. They said they didn’t have any native integrations, but promised that “you can integrate anything with our API.”

This was exactly the type of hidden engineering cost that our team was here to protect against. We pushed back and moved-on.

ActiveCampaign: Eventually ActiveCampaign emerged as the clear winner for its balance of affordability, functionality, and compliance.

We automated the demo request process to ensure that potential providers and partners received immediate responses and clear next steps. This reduced friction in the sales funnel and helped accelerate provider adoption. Below was how the request and response flow was structured.

Request A Demo

Request a Demo Automated Response

Challenge #4: Shipping Product Analytics and GTM Reporting v1

Let’s talk about dashboards.

In many startups, data takes a backseat until a data science team joins a couple years in. Until then, data is usually ad hoc reports coming out of disparate tools, and if they’re cobbled together at all it’s in spreadsheets.

But not here.

We leveraged RudderStack and PostHog to build multiple dashboards for the multiple GTM motions.

This funnel illustrates the patient acquisition journey, from initial outreach to full activation. By leveraging a combination of marketing automation (ActiveCampaign), website interactions (Webflow), data tracking (RudderStack), and in-product engagement (Intercom), we ensured a seamless and data-driven onboarding experience.

We were able to answer questions like:

• Which patient acquisition channels are driving conversions? Flyers in doctor’s offices? SMS campaigns? Email?

• Where are patients dropping off during the activation/onboarding journey?

• How do patient cohorts compare across pilots and over time as our onboarding methodology evolves?

Granular doesn’t begin to cover it. With over 50 charts (yes, 50) and graphs, we gave Consolidate Health the tools to adapt and optimize every step of their funnel.

The Results: Speed and Focus

Consolidate Health had more than just a GTM plan—they had momentum.

• Faster GTM: Tools like Intercom and PostHog allowed them to execute in weeks what might have taken months.

• Significant Long-Term Cost Savings: In the long run, implementing tools like RudderStack and Intercom would likely save Consolidate Health thousands of engineering hours.

• Data-Driven Decisions: Dashboards provided sharp insights into what was working with each pilot, and helped us iterate on our PLG patient-activation and onboarding journey.

A Full-Stack Marketing Partner for a Fast-Paced Startup

At Airframe Labs, we didn’t just act as consultants for Consolidate Health; we became their full-stack fractional marketing team. From strategy to execution, we handled every critical piece of their go-to-market puzzle.

We started with strategy—challenging their DTC assumptions and pivoting to a more targeted and cost-effective B2B2C approach. Once the roadmap was in place, we shifted to execution, standing up a robust RevenueTech stack tailored to their specific needs. Our expertise in marketing operations ensured that every tool, from ActiveCampaign to Intercom, was implemented seamlessly and optimized for HIPAA compliance.

But our involvement didn’t stop there. We built the dashboards that powered their data-driven decisions, giving them granular insights across the acquisition, onboarding, and provider engagement funnels. To round it all out, we provided content support, crafting messaging that resonated with both life science companies and the patients they ultimately served.

In essence, we acted as CH’s marketing backbone—bringing the strategy, tools, and insights of a large-scale revenue organization to their lean, fast-moving startup. It wasn’t just about helping them ship faster; it was about helping them ship smarter, with every component aligned to drive sustainable growth.

Prasid Pathak is a 3-time CMO and 2-time CRO, specializing in building high-performing revenue engines. As a revenue architect, he helps companies optimize their go-to-market strategy and drive scalable growth. With a proven methodology that has consistently helped businesses increase revenue by +20% and +50%,

Prasid works with teams to ship iteratively and deliver results. Follow him on LinkedIn or learn more about his agency Airframe Labs. If you’re looking to transform your business, feel free to get in touch.

Superhuman is known as the premier email app for individuals who craved speed, efficiency, and elegance.

I was an early-adopter and still love it today.

But like many successful scale-ups, it faced a critical question: how do you sustain top-line growth when you start saturating your initial market?

Most startups in this position try to move up market, adding a sales-led motion. Superhuman knew that this would be important, but recognized that there was more to be done. So, in addition, they rethought the core product's role, introducing multiplayer collaboration. This carefully considered set of moves helped set them apart from competitors, and added new viral growth loops.

Here, Gaurav Vohra, founding growth leader at Superhuman, shares the story of how this strategy came to life.

Setting the Stage: The Challenge of Scaling

Prasid: Paint a picture for us—what did Superhuman look like at the time? What was the team structure, and where was the company in terms of growth and revenue?

Gaurav: At that point, we were a startup moving into growth, with just over 100 people. Our marketing team was small—around four full-time employees and three contractors. The growth team wasn’t fully formed initially but eventually converged into about eight engineers, two PMs, one designer, one data scientist, one customer support lead, and one growth PMM.

The initial core team, though, was lean—just a PM, an engineer, an analyst, and a designer.

Prasid: What was the state of the business, and what challenges were you facing at that stage?

Gaurav: When you have a product that performs well, like Superhuman did, you achieve one milestone—stable single player retention in the first year. But then you hit another gravity trap: long-term churn. This is the kind of churn that slowly eats away at cohorts. An example is customers changing jobs every few years and some percentage of them stopping using your product. Eventually your churn and newly acquired cohorts equilibrate.

At this point, you risk growth slowing. We knew we needed to pull levers to get ahead of this.

Exploring the Options: The Paths Considered

Prasid: Before deciding on multiplayer, what other paths did you explore to address these challenges?

Gaurav: There are a few typical moves at this stage:

1. Building new products for new use cases: This is common when you hit saturation. You create new products and charge for them. It’s a way to establish deeper, entrenched network effects across multiple products.

   • Take Readwise, for example. It started as a single product and then launched Reader—a concept that’s 10x more ambitious, better than Pocket and Instapaper.

   • Adobe is another example, with a suite of products that complement each other.

2. Expanding existing product into adjacent categories: If you’re a consumer/prosumer product, you can unlock growth by tailoring your product to meet broader business needs. This could mean adding features for larger teams or, improving security and admin. This requires a lot less R&D than launching an entirely new product. Notion exemplifies this by evolving from a collaborative workspace for teams into a tool an entire organization can adopt. For us, it made more sense to focus on making what we’d already built work for teams. It required less R&D than launching entirely new products, and it aligns with our vision of scaling Superhuman.

Introducing Multiplayer: What Superhuman Built

Prasid: So you made the decision to introduce multiplayer features. What did you build?

Gaurav: Adding team purchasing, team features, and product-led sales was pivotal. This allowed us to go up-market and improve retention, not just at an individual level but for entire organizations.

We built a set of features for teams to collaborate over email, getting more done while saving time and money.

In particular, Superhuman allows users to share email threads with anybody in the world. Others on the team can view and comment on the email directly—without the need for clunky forwards or external tools. It’s a clean, efficient way to collaborate, and it fits right into the workflows our users already rely on.

Prasid: Many productivity tools already cater to teams. What was different about Superhuman’s approach?

Gaurav: Other email tools like Outreach, MixMax, and Salesloft all cater to the sales team. While effective for their purpose, they don’t inspire the kind of love that comes from dramatically improving an individual’s life. Superhuman approached multiplayer differently. We brought our robust individual-focused experience to teams, amplifying what makes Superhuman exceptional.

Prasid: What specific pain points were you addressing?

Gaurav: One of the biggest was how teams collaborate over email. People were screenshotting emails, forwarding threads, or using Slack to share context—painful and inefficient workarounds. We validated this through hundreds of user conversations. Once we knew the problem was real, the question became: how do we design a seamless, cohesive experience that makes collaboration frictionless?

Prasid: What did the implementation look like?

Gaurav: An iterative approach is crucial. We shipped small multiplayer features early—for example, shared snippets, shared read statuses—and iterated based on user feedback. Once we saw traction, we built more comprehensive functionality, like thread sharing and collaboration.

Structuring for Success: Designing Growth Pods

Prasid: Great. So the product team has their vision of what they’re going to build. On the growth side, you now have to build a team to distribute it. How did you structure the growth team?

Gaurav: I led the formation of two growth pods:

1. Expansion Pod: Focused on team growth through multiplayer, virality, and surfacing sales leads.

2. Activation Pod: Constantly improving the new user experience to improve activation, reduce churn, and drive virality.

These pods worked closely with our core team, who builds functionality. For example, the core team ensured features like thread sharing and commenting work seamlessly, even offline. Meanwhile, the growth pods drove adoption by surfacing these features, educating users, and creating viral loops.

Key team members included Growth PMs, tightly aligned with Core PMs. Within sales, we needed Rev Ops and a Head of Sales who truly “gets” both product-led growth (PLG) and product-led sales (PLS). Data scientists supported marketing, growth, and sales, ensuring tight coordination between these functions.

Prasid: What did you look for when hiring for the growth pod?

Gaurav: We needed people who could ship fast—that’s the key DNA element we looked for.

We also sought individuals who could think beyond their domain. For example, engineers who think like product managers, PMs who think like designers, and analysts who can write code. This cross-disciplinary mindset not only speeds up the process but also ensures team members can pinch-hit when needed and challenge each other effectively.

Prasid: Tell us more about what the expansion pod worked on.

Gaurav: Expansion in particular has been focused on driving the multiplayer viral loops.

Their Core team counterpart is deeply focused on making the actual functionality work.

But even with the functionality you still need to do all the following:

• Draw user attention to thread sharing and commenting

• A surface area for not-yet-users to engage with shared threads

• Make the act of sharing or commenting send compelling notification emails

• Efficient conversion paths from being a 'casual' engager to actually being a user

This is a classic “Core creates value, Growth distributes value" split. 80% of the value that is built can be left on the table if you don't have a group focusing on distributing value.

Prasid: This viral loop is a cool idea—the idea of a "surface" so that you don't need to be a paid subscriber of Superhuman in order to collaborate on a thread that's shared with you. This is true PLG as opposed to marketing-led growth.

Prasid: You had also previously mentioned standing up a PLS motion - which is not something Superhuman had up to this point. How did PLG and PLS work together?

Gaurav: Think of it as an escalator. PLG drives self-serve adoption and tees up customers for PLS. We approached PLS in two stages:

• Echelon 1: This stage focused on engaging users who showed strong signals of interest, like specifically requesting to talk to sales—referred to as 'hand raisers.' We staffed a sales team—including account managers, CSMs (Customer Success Managers), and SDRs (Sales Development Representatives)—to directly handle these high-potential leads. This lets us capitalize on the strongest opportunities effectively.

• Echelon 2: This stage targeted users exhibiting weaker signals of interest. Unlike Echelon 1, this approach leaned heavily on data-driven plays to identify potential opportunities and automated outreach. Conversion rates in this stage were typically lower, as the leads were colder and less engaged. Many companies make the mistake of starting here, but it’s far more effective to focus on Echelon 1 first.

Multiplayer functionality sped up every part of this escalator, making the system more efficient and scalable.

Measuring Impact: Success Metrics

Prasid: How did you measure success? Can you share any specific metrics or outcomes that highlight the results of this strategy?

Gaurav: The results were significant:

• Launching thread sharing and commenting saw the highest weeks of expansion revenue in Superhuman’s history.

• Teams that adopt collaborative features grow seats and revenue at twice the speed of teams that do not.

• At the same time, we began closing some of our largest enterprise sales opportunities, showing clear traction with bigger customers.

What worked best was we introduced viral loops and workflows that didn’t previously exist, and they drove engagement in ways we hadn’t seen before.

However, there were challenges. We were building something quite radical, and there was inherent risk. Creating a way for teams to collaborate on email required us to pay extra attention to user education. We included in-app warnings and heads-ups to help users understand what was at stake—guiding them through these changes without overwhelming them.

And taking these updates to customers needed nuance. Collaboration doesn’t dominate the zeitgeist right now. People are focused on AI.

Prasid: Did this influence how you positioned Superhuman during the rollout?

Gaurav: Absolutely. Our core promise remains saving users four hours per week—making Superhuman the most productive email app ever made. We adapted this messaging to reflect what’s relevant today: “Collaborate faster and get more done with AI-powered email.” We placed collaboration and AI on the same level in our messaging hierarchy.

Lessons Learned and the Future of Growth

Prasid: What are your biggest takeaways?

Gaurav:

1. Start on core swings early—they’ll take longer than you think.

2. Avoid over-optimizing one area of the growth funnel. There are diminishing returns, and it’s better to take a holistic approach.

3. Speed of iteration / speed of shipping is the most important leading indicator. Teams that proactively find ways to ship faster will win.

Superhuman’s expansion to multiplayer wasn’t the next logical step in a standard SaaS playbook—it was a bold move to evolve what an email tool is. Superhuman deepened its existing offering, showcasing a thoughtfulness that’s a core part of their identity.

For companies, the lesson is clear: the best growth solutions often involve changes to the product. Start with first-principles, look for the road less traveled, and let the customer be your guide.

Gaurav Vohra advises startups on growth — including product, marketing, and analytics. He is a growth specialist, leader, and advisor. He has built Superhuman from the ground up — having led Growth, Product, Marketing, and Analytics. Currently, he advises founders on growth. His focus is Product-Led Growth SaaS. Follow him and connect on LinkedIn.

Stop Thinking You’re Too Small for Partnerships

The startup world loves its playbooks: raise funding, build a product, hire an outbound sales team, and pray you start getting customers. Partnerships? That’s something to think about when you’re a 500-person company with a BD team and ample time to build integrations.

Except that’s not true.

The conventional playbook says to wait until you’re “big enough.” Cailen DSa disagrees. He believes Partnerships can be a multiplier for scrappy startups striving to punch above their weight. Below Cailen shares how he took what he’d learned at Box and Dropbox to lead early GTM partnerships at Front.

Why Startups Get Partnerships Wrong

Prasid: Let’s start with a common misconception: partnerships are often seen as something for later-stage companies. Why do you believe startups should prioritize them early?

Cailen: Most early-stage founders think, “We’re too small to partner with anyone meaningful. We don’t have anything to offer.” But that’s not true. Partnerships aren’t about size—they’re about alignment. If you find just a few partnerships with incredible alignment, even a small startup can offer value to much larger players.

At Front, when we were just a 50-person team with $5-6 million in ARR, we started investing in partnerships. This contrarian bet paid off big. Partnerships became Front’s highest converting channel and drove 40% of our top-of-funnel (TOFU) leads, outperforming paid acquisition. What made it work was a narrow strategic focus. We didn’t invest massive resources; we just needed to solve a real problem for a single partner.

How Front and Talkdesk Built a Win-Win Partnership

Prasid: So take us back. What’s the situation at Front just before you launched the partnerships strategy?

Cailen: We had about 5,000 customers, and we were just starting to see some organic growth. But we didn’t even have a marketing team yet. We were thinking about hiring one, but for the most part, it was all very scrappy. The sales team was incredibly lean but resourceful. We had 15 reps, and I assigned three of them to different projects that would improve some metric or process. The sales team also had a team-wide goal, which helped focus everyone’s efforts.

It wasn’t just sales—we were doing everything we could to generate growth. I was running events out of the sales team. It was all about finding ways to make things work without relying on big resources or budgets. Partnerships fit right into that scrappy mindset, but it also gave us a path to scale.

Prasid: I love this. It sounds like in a lot of ways you were sort of a “full stack” GTM leader - not just driving sales but also driving event marketing and now BD.

Cailen: Coming from Dropbox and Box, I already knew how impactful partnerships could be. It wasn’t an original idea I came up with—just something I had seen work before. At Box, we started building partnerships when we were about 50-60 people, and at Dropbox, we implemented a different flavor of partnerships later on.

At the time, Front was primarily an SMB-focused customer support ticketing product. We had a long-tail customer base and small ACVs. Talkdesk, on the other hand, was a voice-based contact center solution targeting the mid-market and enterprise segments. They were bumping up against a product gap at the time related to their integration with Zendesk.

But to do that, Talkdesk needed to show they had a ticketing integration to round out their solution. By partnering with us, they were able to “check the box” and enhance their value proposition. On our side, the partnership allowed us to move up-market and land enterprise customers that were previously out of reach and difficult to engage.

Prasid: So you decided to pursue a partnership with Talkdesk. What was step one—how did you implement it?

Cailen: Step one is always finding the right people to talk to. In this case, I think we got connected to Tiago, their CEO, through a mutual investor. But before we even reached out, we already had market signals pointing us in their direction.

Customers were asking us, “Do you have a Talkdesk integration?” This feedback wasn’t just anecdotal—we had built a system for tracking feature requests across tools like GitHub and Jira. Our PMs wanted us to systematically and programmatically track these requests, so anytime a customer asked for a specific feature or integration, it went into a feature request repository. We also tracked this data in Salesforce, so we had a clear view of what was blocking deals.

When we stack-ranked these requests, cloud call centers consistently came up. That gave us confidence that partnering with Talkdesk wasn’t just a guess—it was grounded in real customer demand. Armed with that data, we reached out and set up an initial meeting with their head of partnerships.

Prasid: What did those early conversations look like?

Cailen: Because we were the B-side in this equation based on revenue scale, they were essentially the A-side— hence we approached it strategically. Our pitch was simple: “This is a one-plus-one-equals-three situation.” Talkdesk was looking to fill a product gap, and we could deliver on that. We positioned ourselves as a partner that could help them compete more effectively by rounding out their offering via partner vs build.

It’s worth noting that at this stage, we’d never done real partnerships before. A little bit of it was posturing—we’d say, “Yeah, we’re heading in this direction too,” while piggybacking on their strategy. Our main goal was to get them interested enough to integrate with us because we knew it would unblock deals and address a clear market demand.

Ultimately, I think we got lucky that they saw the mutual fit. At the time, they already had integrations with Zendesk and Desk.com (owned by Salesforce), and partnering with us aligned with their strategy of working with companies that could complement their core product.

In my opinion, when you’re a startup, you often have more to gain than the larger company does. It’s not always easy, but sometimes you can convince them by showing how you fill a clear product gap for them today, while also making the case that in two to three years, you’ll be a much larger player. It’s about demonstrating both immediate value and long-term potential.

Prasid: Once the partnership was underway, how did you manage the technical integration? What steps were involved in getting both product teams aligned?

Cailen: The first step was working closely with our product team to figure out who was going to build the integration and how it would work. We had to assess things like:

• What technical requirements were needed for the integration?

• Do they have open or public APIs?

• What parts of their API are exposed, and what’s required to connect our two systems?

It was really about doing our due diligence on the technical side, determining who would handle what, and connecting both product teams to collaborate.

Prasid: Since you’ve mentioned being the B-side in this relationship, did that mean taking on more of the development work?

Cailen: Yes, absolutely. As the smaller player, we were willing to take on more of the development. In this case, they already had most of the APIs we needed because they’d built an integration with Zendesk. That made things easier for us. We took on most of the integration work, and it went pretty smoothly.

It took a little while—the partnership cycle, so to speak, lasted around 6 months. But while we were working on the integration, we were also building the relationship, so it wasn’t just about the tech. It was about aligning our teams and strategies along the way.

Building a Partnership Framework That Scales

Prasid: Partnerships often feel overwhelming for startups. How did you approach building a framework that could work for a small team like Front’s?

Cailen: It’s all about focusing on what matters and starting small. Partnerships don’t need to be perfect from day one, but they do need to deliver value on both sides. For us, the strategy came down to three key principles: (1) align on strategic value; (2) target partners 10x bigger; and (3) start small and build trust.

Talkdesk needed an alternative ticketing partner to Zendesk. Someone that had no ambitions to get into call centers. We became that alternative by providing exactly what they lacked.

The alignment didn’t just create new opportunities—it drove some of Front’s largest logos over time. Complementary value is unlocked when two products connect in a way that amplifies their respective strengths. Talkdesk brought voice to the table, and we brought ticketing.

Prasid: Starting small sounds simple, but what does that actually look like?

Cailen: We didn’t ask for a full product integration on day one. Instead, we focused on low-lift efforts that built momentum and trust:

• Co-branded materials: We created one-pagers and cheat sheets to make it easier for both teams to communicate value to their audiences.

• Conference collaborations: We shared stages at events, presenting the partnership as a united front.

• Co-selling motions: Both sales teams were incentivized to share intelligence, refer prospects, and eventually walk opportunities in the door.

By starting small, we avoided overwhelming our product and engineering teams. It also gave us early wins to show both teams that the partnership was worth investing in.

Prasid: How do you structure incentives to make partnerships successful? For example, how do you ensure both your team and the partner’s team see value in referring or closing deals?

Cailen: There are a few frameworks you can use for partnership incentives, and it really depends on the type of partnership and what works best for both sides.

The first is a revenue share or referral model. In this setup:

• The rep who successfully refers the deal receives a payout, which is typically a percentage of the deal’s revenue.

• On the low end, this could be 3% of the deal, while on the high end, it might be up to 30%, depending on your gross margins. But the standard is usually around 10% of first year revenue.

• Some companies structure this to apply only to year one of the deal, while others might extend it to perpetuity. Personally, I try to avoid perpetuity deals and stick to year one to drive higher LTV.

The partner’s team can decide how to allocate the revenue. Often, they’ll split it: part of it goes to the partnership team to demonstrate profitability (so they can justify being a profit center, not a cost center), and the rest might go toward spiffs for account executives who referred the deal. It’s all about showing the value of the partnership and making the incentives clear.

Another framework is a deal referral model without revenue sharing. In this case, the partners simply refer deals to each other without a financial incentive. This is simpler but relies heavily on mutual trust and alignment of goals.

A third option could be a distribution partnership, which might apply more to consumer-facing models. For instance, if one partner drives a certain threshold of sign-ups or new user volume, the other pays a predetermined amount.

For me, the priority is always to make it lucrative and a no-brainer for the partner. At the end of the day, as the smaller company, I have more to gain than they do. My goal is to show we can drive qualified opportunities for them, which is what they care about most—more deals for themselves or improving their win rates because we’re filling a critical gap.

Addressing Internal Resistance

Prasid: If I were the CEO, I might worry that incentivizing partner co-selling could be a distraction from actually hitting sales numbers. How did you handle concerns like that?

Cailen: That’s a common objection—sales teams worry it distracts from hitting quotas, and product teams think integrations pull focus from the core roadmap. Here’s how we thought about it:

1. Start at the right time: We started making this partnerships bet at $2-3M in ARR. By then, we had a healthy-sized team of about 50 people—25 in engineering and product, and 25 in the sales org.

2. Start small: We didn’t ask for a full product integration. Instead, I convinced the new VP Marketing to do some partner enablement: 1-pagers, a landing page for partners, and enablement collateral for both sides.

3. Focus on 10X opportunities: At that stage, the board was pushing us to grow faster. Just grinding-out every-deal to hit quotas wasn’t going to cut it. But we didn’t create a holistic partnership program with 10 partners. We focused on a single partner that was 10X bigger, where there was incredible alignment and a similar ICP. It was a way to open up a completely new channel, expand our marketing reach, and engage their existing enterprise customers.

The Long Game: Why Partnerships Matter More Than You Think

Prasid: What happened once the partnership with Talkdesk took off?

Cailen: It became clear that partnerships weren’t just a growth channel—they were a growth multiplier. At Front, the Talkdesk partnership created a ripple effect:

• Introductions to new players: Talkdesk’s network became a bridge to customers, partners, conferences, and analysts.

• Social proof: Being endorsed by Talkdesk gave us credibility with larger customers and partners.

• Compounding ROI: Each new integration multiplied the channel’s impact, creating long-term growth far beyond the initial investment.

Partnerships don’t just add value—they multiply it over time. For these prospects that were getting walked in the door, the conversion rates were 10X higher, resulting in a CAC that was much better.

Prasid: Just stepping back for a moment, it’s kind of rare to see a head of sales take on things like running events, making swag, and then launching partnerships themselves. That’s pretty cool.

Cailen: Yeah, I guess a lot of that comes from being a 0-to-10 or 0-to-20-million-dollar ARR VP of Sales. That’s the stage I’m best suited for and where I enjoy working the most. It’s more freeform, and you can be creative and think outside the box. Once you move into the 20-to-50 range, the playbook becomes more predictable, and while I’ve done it, I find the earlier stage more exciting.

But there’s also another layer to it. If you don’t hit your number, you’re fired. Your back is against the wall constantly every quarter, and you have to be thinking thinking 12 months in advance because you know quotas and targets are only going to keep going up. There’s a kind of desperation that forces you to ruthlessly experiment. That mentality drove a lot of our approach.

It’s also ego, to some extent. You want to prove you can survive and thrive in the role. The average tenure of a CMO or VP of Sales is 16-18 months because we’re all signing up for quantitative targets. My personal goal was simple: survive longer than the average—I can last 4 years at a company—and leave knowing I added value. By the time I left, I knew my stock was a lot more valuable than it was when I joined.

From Front to RevenueCat: Scaling the Framework

Prasid: Have you applied this framework elsewhere?

Cailen: Absolutely. At RevenueCat, we tackled a very different market but applied the same foundational principles. RevenueCat’s core ICP was developers—almost every developer working on mobile apps that use subscriptions. These developers faced a huge infrastructure challenge: syncing subscription states across iOS, Android, Roku, Amazon App Store, and other platforms.

It’s a lot of work to keep the subscription states in sync with the app store, and many developers had to build custom code just to poll devices and make sure subscription states were active. This wasn’t just tedious—it was distracting developers from focusing on their core product.

RevenueCat had already built integrations because developers were asking for them. But here’s the insight I gained: The reason devs were asking wasn’t just technical—it was because their business counterparts wanted full-cycle & funnel attribution. For example, if someone ran an install ad, they wanted to see downstream data that showed whether it worked. Without integrations, teams had to build custom tools internally to get this data.

That’s where partnerships came in. To solve this, we ended up building an ETL pipeline that made it easy to cut the data in different ways. Once we had that infrastructure in place, we partnered with tools that complemented developers’ workflows—helping them solve attribution and reporting challenges at scale.

The result? These partnerships didn’t just fill a gap; they continued to drive significant TOFU growth for RevenueCat. I’ve heard it still drives a lot of TOFU for them, which goes to show that once you get partnerships right, they create leverage far beyond the initial investment.

Final Thoughts: Start Now, Start Small

Prasid: What advice would you give to early-stage founders who are hesitant to pursue partnerships?

Cailen: Stop waiting. Too many startups think partnerships are something you do when you’re bigger. That’s not true. You can take lower-lift actions even before building integrations. Start with affiliates, lead referrals, or revenue-share agreements. Partnerships don’t take as many resources and cycles as people think.

The key is alignment. Try to find someone where you’re filling a gap for them in their ecosystem. If you can identify what your potential partner truly needs and deliver on that, you create more than just growth—you create leverage. Partnerships have the power to multiply over time, opening doors to new ecosystems, building credibility, and delivering long-term returns far beyond your initial investment. You don’t need to overcommit on day one. You can start small, iterate, and scale as you go.

Cailen DSa is the Founder of T2D3—a COO/CRO consulting firm supporting founders, executives, and employees from $0 to $100m+ ARR. He is also the Co-Creator of Silicon Sands, a private San Diego Founder/Exec/VC Network with over 200+ members. Follow him and connect on LinkedIn.

Slack revolutionized workplace communication, becoming a household name among collaboration tools. But when it came to generating revenue, Slack faced a unique challenge: how to monetize a free product that was already delivering so much value. As the company prepared for its IPO, the pressure increased —the monetization team needed to show Slack could accelerate revenue growth without causing churn.

Enter Shikha Kaiwar and the Monetization team, who turned Slack’s freemium model on its head.

In this interview, Shikha shares the story behind this pivotal moment—at the heart of their strategy was a shift from freemium to free-trial. It was a high-stakes move that required cross-functional collaboration, sharp user insights, and a willingness to challenge assumptions. It was risky. It was necessary. And it worked.

Pricing: A Transformative Lever for Revenue Growth

Prasid: Shikha, what was the boldest initiative you led at Slack, and why did it stand out as a turning point?

Shikha: I was part of the Monetization team at Slack. The shift from a freemium model to auto-enrolled trials was the most transformative project I worked on. We had a strong culture of experimentation, with shared metrics between product and marketing teams. But over time, the smaller, incremental experiments we had been running began showing diminishing returns.

We realized we needed a bigger bet. That’s when we proposed testing a 30-day free trial, where users were automatically enrolled into the paid version of Slack upon signup. It was a significant departure from our freemium model, but we took an experimentation-first approach, validating it on a smaller scale before rolling it out.

The results were incredible. It became a North Star for the company, driving a 20% increase in paid teams within the first year and reshaping how we thought about monetization.

Rethinking Trials for a Freemium Audience

Prasid: Many companies use free trials. What made Slack’s approach unique?

Shikha: Most free trials follow a conventional playbook: set a standard duration, require credit card information upfront, and rely on generic user flows. But Slack’s freemium model was different: the free tier was already so robust that users often didn’t feel the need to upgrade. The free version was “good enough,” so we had to rethink every aspect of our pricing and the paywall to address that mindset.

For example, we asked ourselves:

• Would requiring a credit card discourage Slack users from engaging with the trial?

• How long should the trial be to showcase the full value of the product?

• What’s the right balance between educating users and overwhelming them with prompts?

Instead of copying what other companies were doing, we tailored every decision to Slack’s unique audience.

Prasid: How did you figure out the answers to those questions?

Shikha: As a product marketer, I needed to understand the user journey inside and out—what they were thinking, what they needed to know, and when they needed to know it. For example, if users were highly active in the product, we leaned into in-product prompts. If they were less active, email became a key channel for re-engagement.

Implementing Experiments And Collaborating Across Teams

Prasid: Tell us about what you implemented, and how you coordinated such a big change.

Shikha: Our team consisted of the lead product manager, product designer, engineers, and me - the growth PMM. We worked closely with Customer Support and Marketing Ops such as the email team.

I also owned other out-of-product touchpoints such as the Help Center, and creating a new landing page.

We iterated on the trial a couple of times before rolling it out. Our talented design team made a prototype that we validated with some users, and we also used UserTesting to understand the perception of the trial and the value prop to shape the messaging.

Then we rolled it out in waves over a few weeks, staying very close to catch any bugs or feedback. I was in every discussion regarding the product and I owned all messaging and marketing comms around the trials. I created new onboarding emails and led all content inside the product as well.

Prasid: What were some of the challenges with the roll-out / experiment?

Shikha: One of the biggest challenges was balancing the needs of different teams. For example, our sales team had concerns about how the trial might impact their pipeline, while customer support wanted to make sure the messaging was clear enough to minimize confusion. We had to address these concerns collaboratively, ensuring everyone was aligned on the bigger goal.

A second challenge was user education. A free trial only works if users understand the benefits of the paid tier. We focused on showing users what they could achieve with features like unlimited message history, Slack Connect, and advanced admin controls.

Moreover, it was less about simply tracking how many users were on paid plans versus free ones and more about understanding what paid users were doing within Slack. For example, with a feature like Slack Connect—where users can share a channel with other companies—we saw high engagement in the metrics and user feedback. This joint input from product and marketing indicated that Slack Connect was truly valuable. From there, we worked backward and decided this was something that should be part of the paid experience.

Prasid: You mentioned the pricing page. Did you conduct any specific tests on that page to improve conversions?

Shikha: Yes, we ran a significant number of tests on the pricing page—many of which were driven by marketing but informed by product insights. These experiments covered everything from plan descriptions to the ordering and sequencing of features.

One key area we focused on was ensuring users understood each feature’s value. For instance, if we highlighted ‘Slack Connect’ as part of a premium plan, we had to assess if users actually knew what it was and why it mattered. If there was any ambiguity, it became a priority for us to clarify that value proposition.

Measuring Impact and Iterating

Prasid: What results did you see after rolling out the trial, and how did you continue improving it?

Shikha: The trial drove a 20% increase in paid teams within the first year, which was a huge win. But we didn’t stop there. We continued testing and refining the experience, focusing on the messaging and feature highlights that resonated most with users.

Having shared metrics with the Product Team was instrumental in us working together. Increasing monetization was not a product or marketing problem, it was a team problem, and it allowed us to collaborate and put the customer first to create a delightful experience.

We aligned on a joint metric: increasing the number of teams converting to paid plans each quarter. For example, our goal was to have 100 more paying teams than the previous quarter, with each department accountable for contributing to that growth.

A collaborative metric allowed us to design a user experience that felt cohesive and engaging. Pricing, while a product-driven metric, requires a seamless handoff from in-product experience to out-of-product education. Discussing pricing details in-product can interrupt the user’s experience, so instead, we leveraged marketing channels—like email—to add context. The goal was to empower users to see the product’s value first and then recognize why upgrading was worth it. Through this, we created a journey where marketing educated and guided, and the product experience spoke for itself, leading to an increase in user satisfaction and revenue alike.

Prasid: What insights did you gain from testing different pricing strategies? Were there any surprising results that shaped your approach?

Shikha: One of our more interesting findings came from experimenting with two paid plan options—a standard tier and a second, more premium option. We initially tried positioning the second tier as the ‘Most Popular’ by adding a tag to encourage more users to choose it over the free version. However, this actually had an unintended effect: it ended up cannibalizing overall monetization. Users started choosing the middle option over both the free plan and the highest tier, which completely removed demand for the top tier.

We didn’t expect it to impact existing customers on the higher plan, but it even created challenges downstream for our sales team, who struggled to upsell users to the premium tier. By signaling that the middle plan was the most popular, we unintentionally devalued the top option.

This experiment taught us a valuable lesson about positioning and user perception. Rather than pushing users toward the middle tier, we realized we needed to articulate the specific value of the premium option. Helping users understand the distinct benefits of each tier allowed us to strike a better balance between plans and improved overall conversions.

Lessons for Growth Teams

Prasid: You’re now doing growth and product marketing consulting for startups like Dive, Easol, Graphy, AppliedXL, and more. What advice do you give to other companies looking to drive revenue growth through experimentation?

Shikha:

1. Tailor your strategy: While transitioning from freemium to free trial is a common SaaS pricing journey, the details of how you do it should be totally unique to the context of your customer pain points and your solution. Understand your users, the benefits that most-resonate, and then tailor your pricing tiers.

2. Don’t underestimate email: When users are new, chances are they aren’t spending much time in your product. Email is a great channel to engage them and get them the info they need to start using it. Even when users are in-product, interrupting them to talk about pricing can be awkward. Once again, emails, driving to a pricing page, can be a more elegant way to bring-up pricing.

3. Align metrics across teams: Shared metrics foster collaboration. At Slack, product and marketing worked together towards the same goal, which made our efforts more effective.

4. Think big, validate small: It’s easy to start testing everything and end-up seeing only small incremental gains. To see big impact, you need to design big bold experiments. But always validate your big ideas on a smaller scale before going all-in.

Prasid: For the startups you advise today, that maybe don’t have a team as big as Slack’s, how is the approach different than big companies like Slack?

Shikha: For early-stage or founder-led companies, I often suggest starting with qualitative insights. Talking directly to customers can provide a sense of what resonates, even if it’s not a formal A/B test. Observing patterns in customer feedback, like recurring questions or common themes, can be incredibly valuable.

When full-scale experiments aren’t feasible, I advise companies to focus on smaller indicators of engagement. Are users asking follow-up questions? Do they show active interest, or are they disengaged? Tracking these signals and keeping a log of feedback over time can help identify what’s working and inform the next steps, even without large datasets.

Prasid: This is such an important point. Everyone says you need to talk to your users, but even so, it’s sometimes intimidating, or it can feel time-consuming, and so it often falls by the wayside.

Shikha: Making such a big change taught me how to use experimentation in a smarter way. A lot of growth culture tells us to “test everything.” But every test costs time. With Slack’s journey we needed to show explosive revenue growth, which meant you have to do something big. This test also marked the first time we leaned into marketing to educate users on the value of Slack, especially using email. Email became a big driver of monetization, ironic for a product that is supposed to be an email replacement!

Ultimately, it’s about building an iterative mindset. Even if you can’t run massive experiments, consistently gathering insights, testing new ideas, and listening closely to your users is how you build a product that people love.

Shikha Kaiwar is a Product Marketing, Lifecycle, & Growth Consultant. She has built product and growth loops by taking control of the funnel: solid user personas, messaging that users actually understand, and delightful customer experiences. Her clients include Dive, Easol, Graphy, AppliedXL, Leaf, and Too Good To Go. Follow her and connect on LinkedIn.

Being a revenue leader means living with constant pressure: your targets keeps climbing, you’re perpetually overbooked, but the business is counting on you to bring purpose and energy to every meeting. At some point, sheer hustle stops working. You need tools that amplify your impact without burning you out.

Over the years, I’ve developed a personal tech operating system that helps me manage time, energy, and priorities. This isn’t about trendy apps—it’s about ruthlessly optimizing your day to gain leverage and maximize your impact.

📌 The contrarian rule of tools: Use fewer, use smarter

In a world obsessed with productivity, there’s a dangerous tendency to believe that more tools equal better results. But the truth is that every app you add to your stack incurs hidden costs. Time to learn it. Time to integrate it with your workflows and those of your team. And remember: every moment spent migrating between tools you’re actually driving backwards paying down debt instead of moving your business forward.

Instead of chasing the latest shiny app, focus on building a lean, tightly integrated system.

Here’s what I’ve found:

1. Integration is king. The best tools aren’t just great at their core function—they play well with others. Your calendar should talk to your task manager. Your emails should integrate with your CRM. Every piece of your system should fit together.

2. Eliminate overhead. The fewer tools you use, the fewer notifications, updates, and logins you have to deal with. Simplicity reduces cognitive overload, freeing your brain for the work that matters.

Here’s how I scale myself:

◾️ (1) Motion: Automate scheduling of tasks, protect your priorities

If you’ve read the best productivity books like 7 Habits or Getting Things Done, you’ll know that one key tenet is that it’s not enough to have task lists, you need to schedule tasks.

Motion doesn’t just schedule—it adapts, protects, and optimizes your time.

• Tasks get auto-scheduled and re-scheduled: When I decide I need to get a task done, I’ll add it to Motion. Motion automatically blocks-off time for that task on my calendar. And if a meeting gets booked over it, the tasks automatically floats down to the next available spot.

• Multi-calendar automation: Similar to Calendly, I can share a single booking link via Motion that pulls availability from all my calendars (one per client, plus personal).

• Floating gym sessions: My 75-minute workout block floats to the next available slot if a meeting overlaps. If there’s no free time left, Motion locks the calendar to prevent overbooking. This means self-care gets the same respect as any board meeting.

Most people think productivity is about packing more into the day. Wrong. It’s about ruthlessly protecting the things that matter most—and automating the rest.

One big negative of Motion: It doesn’t integrate with Asana, which is where the Airframe Labs team stores our tasks. This is definitely a big drawback: I have to manually move “Today’s” tasks from Asana into Motion every day.

◾️ (2) Notion AI: The fast-track to better first drafts

Notion AI is a content force multiplier. Unlike ChatGPT, which isn’t familiar with my voice and my content, Notion has all our LinkedIn content from the past 6 months, and all my Substack content from the past 7 years.

• Search: I’m always recycling concepts. Notion makes it easy for me to search “Prussian General” (I can never remember his name) to find that concept I love about the benefits of lazy generals.

• Generating new content: Unlike ChatGPT, Notion AI leverages my existing writing database, drafting LinkedIn posts, Substack articles, and outlines that I refine into my authentic voice.

• Editorial calendar: With my team, we’ve built a shared system in Notion to organize ideas, track drafts, and surface stories worth retelling.

I heavily rewrite everything, but Notion gives things a good jumpstart.

◾️ (3) Superhuman: For Pre-Written Snippets, AI-Scheduling, Keyboard Shortcuts, and so much more

Superhuman isn’t just faster email—it’s a mindset. I originally migrated because tabbing between 4 Gmail accounts was super-slow. I just wanted a way to quickly toggle.

• Snippets save time: Pre-built templates for everything from candidate responses to introduction emails eliminate repetitive typing. I’ve created these “snippets” (templated content blocks) that I can drop into emails like a standard response for candidates to schedule interviews, or a standard response for making intros.

• AI-powered scheduling: The “Create an Event with AI” feature slashes the back-and-forth of finding meeting times.

• Keyboard Shortcuts: these were probably always a thing in Gmail and Outlook, but Superhuman really pushed me toward a mouse-less email experience.

One big shortcoming: 10 years ago, email was our primary work “inbox.” But today SMS and Slack are just as big if not bigger. If Superhuman doesn’t figure out a way to add value on top of SMS and/or Slack, I don’t know that it will remain a big part of my tech stack.

◾️ (4) Asana: Asynchronous Coordination and Better Alignment

Asana isn’t just a task manager; it’s a delegation tool that ensures alignment and clarity.

I’ve got separate Asana projects for each person on my team and each Customer we work with. Before, I’d often delegate something, and get something back that went way above and beyond the quick-and-dirty solution I was looking for.

• Billable hours field: This custom field helps me right-size effort to impact, preventing over-engineered solutions for small tasks.

• Quick task capture: Context switching between businesses is taxing. So rather than relying on my memory, I store all deliverables in Asana so I know what I owe, and when. From there, it’s also really easy to add it to someone else’s Project, so that I remember I want to discuss it in our next 1-on-1, and they know this delegated task is coming.

• Async updates: Because you can see a log of changes on an Asana card, as well as comments, it’s easy to see where a project is in the process. It’s way better to have all that meta-data living on the project card vs. all over email + Slack.

• Jump into work without thinking: Context-switching between meetings and between the different businesses we work with is incredibly taxing. Rather than having to sit down and think about what i should work on next, if I have 10 minutes free between meetings I can just grab what’s on-top in Asana.
  
  I triage once a day. And I try to break big tasks into smaller things, so that when I have 10 minutes between meetings, I don’t have to think about what to do next, I just pick something up.

◾️ (5) Fathom: Never Take Notes Again

If you’re like me, meetings can be a double-edged sword. They’re critical for driving decisions and alignment, but they also demand a lot of focus—and trying to take notes while staying engaged is nearly impossible. That’s why Fathom can be an indispensable part of one’s tech stack.

• Stay present and let AI handle the notes: Fathom records, transcribes, and summarizes meetings in real time. Within 30 seconds of the call ending, I can have a detailed summary in my inbox. No scrambling to remember key points or action items—it’s all there, ready to go.

• Sharing made simple: If you dread summarizing meeting highlights for your team, with Fathom you can share specific video clips of key moments instead of writing lengthy recaps. It’s especially useful for dropping context into Slack or follow-ups.

• On-demand insights: Fathom’s AI assistant is a game-changer. If you need to reference a decision or action item from a previous call, you can just ask, and it delivers the answer instantly. It’s like ChatGPT, but for meetings.

I’ve realized that the value of a meeting isn’t in the time spent—it’s in the follow-through. Fathom ensures you can capture every critical detail without sacrificing your focus during the call. By freeing up mental space, you can focus on the bigger picture while ensuring no detail gets overlooked.

Why this matters: Scaling yourself is the growth leader’s edge

Tools don’t scale you—systems do. The right tech stack, used with intention, can transform how you work, allowing you to focus on high-impact activities while staying sane in a demanding role.

If you’re a growth leader, it’s time to stop thinking of productivity as a hustle game. Instead, think of it as leverage.

The goal isn’t to have the most powerful tools. It’s to have the right tools used with the least friction. A lean tech stack forces you to be intentional, prioritize clarity, and focus on what really drives outcomes.

Start by auditing your current stack. Ask yourself:

1. Does this tool solve a critical problem?

2. Do I use it daily or weekly, or is it just taking up space?

3. Can I consolidate its functionality into another tool?

Cut ruthlessly. Simplify unapologetically. You’ll discover that fewer tools don’t just make your life easier—they make you more effective.

What’s your go-to tool for scaling yourself? Drop your thoughts in the comments or hit reply—I’m always looking for smarter ways to work.

Enough about Big-Hairy-Audacious Goals. Let’s stalk about small consistent habits that compound for big impact by 2025:

🟠 Team & Task Management: Driving Efficiency and Motivation (4 habits)

1. Celebrating Small Wins Builds Belief in Our Agency

The mistake I see leaders make is setting Big Hairy Audacious Goals and then failing to hit them.

This erodes the team’s belief that they can actually do what they set out to do, creating a negative feedback loop where they get demoralized and become less ambitious.

Instead, continuously remind them of the milestones they’re achieving to build momentum toward the big goals.

2. Delegating Everything Feels Icky But Can Actually Empower

Avoid giving yourself action items.

When I was younger, I wanted to show my team nothing was too big/too small for me. That I could roll-up-my sleeves.

The mistake I see leaders make is when they’re pulled in so many directions, they become a bottleneck on projects. If folks see the same projects stalled week after week because the leader isn’t prioritizing it, it hurts morale and normalizes missing deadlines.

The solution: don’t allow yourself to have any action items. Focus on having output through others. It can feel icky: it almost seems like you’re trying to avoid work, but it can be a relief to your team, who is now able to ship faster and feel more accomplished.

3. Focus on Trends, Not Snapshots

Don’t report on what the KPI is today - report on the trend line over time.

Snapshots don’t show progress. Every team should have a north star metric and know how it’s trending.

When reviewing metrics, ask your team to answer 3 questions:

• Is this moving positively or negatively over time?

• Why is it moving that way?

• What are we doing about it?

This does three things:

1. It forces the team to get better week after week

2. It forces understanding: if they don’t understand why the number is moving the way it’s moving, how can they hope to improve it

3. It forces projects to intersect with impact. If the answer to “what we we doing about it” is “we don’t have time because we’re busy doing projects that don’t move the needle” then either you’re not working on the right projects, or your not measuring the right impact.

4. Align Effort with Impact

Align effort-to-impact by assigning project impact estimates upfront.

I get frustrated when I see team members dumping 20 hours into something low-priority. I realized it happens because they either don’t have as strong an instinct about what’ going to move the needle, or they don’t have as clear visibility into all the other things we could be working on that could drive more impact.

Now iI try to nip this in the bud with a growth prioritization process like ICE, so everyone can see all the projects we considered and what we chose to prioritize. By establishing what each project is “worth” upfront - the team can right-size their effort to the impact.

🟠 Growth & Learning: Creating Opportunities Beyond the Office (1 habit)

5. Make Time for In-Person Events

I work remotely, so in-person meetups are hugely enriching and lead to new opportunities.

Whats unique to me, is that as a growth consultant, in-person networking is driver of net-new opportunities for our business.

But regardless of your role, I’ve found networking events also give me a place where I can funnel people who I want to see but don’t have time to grab 1-on-1 coffees with.

🟠 Personal Growth: Habits for Self-Improvement and Team Connection (2 habits)

6. Ask Every Team Member to Talk to At Least One Customer

I ask every new marketer joining my team to do a research project.

I pick a question we’re currently grappling with - like “What’s the top reason people churn in week 1?” Then I ask them to interview 3-4 customers and bring back an answer.

It’s an invaluable source of raw signal, and it builds empathy.

Most importantly: interviewing customers is intimidating - you may not know where to get contact info, what permissions you need, or how to run an interview. But my team has gone through it once, they realize it’s not so bad, and they’re far more likely to interview customers again when a new question arises.

7. Stack Habits to Build Reflection Into Your Day

I struggle to make time for things that are perhaps important but not urgent. So to counteract this, I habit-stack.

I have to log my billable hours in a spreadsheet - I’m updating it multiple times a day. So I added my daily log of “did I write?” and “did I meditate” to the same spreadsheet. That way when I’m doing one thing, it triggers doing the other.

These habits may be small, but applied consistently, they’ll transform your productivity and mindset.

Recommended reading:

• When I was talking about Big-Hairy-Audacious Goals, I was referring to Tiktok’s October Theory. Here’s an interesting take from Mark Travers via Forbes where he notes that turning goals into habits might be better in the long run.

• The power of small, consistent habits is transformative, not only for personal growth but also for scaling your startup. A great example of this is focusing on foundational elements, like messaging, which can drive growth across all customer touchpoints—from your homepage to sales decks. Here’s a helpful guide by Alex Estner on building a SaaS messaging framework that strengthens your sales and marketing assets. And if you’re ready to push further, check out his 100+ actionable, proven SaaS growth tactics to accelerate your growth journey.

• Kristi DePaul of Harvard Business Review has highlighted the importance of habit formation in leadership development.

• The Startup CEO discusses the framework of atomic habits in the context of decision-making, emphasizing the importance of tying habits to identities rather than just outcomes.

The first 10 years of my career I was unemployed A LOT. The second 10 years, I’ve done a ton of career mentoring for others. Here’s a framework I invented to help you land hard-to-get jobs. I call it the Tarzan Career Framework:

Think of switching jobs like you’re Tarzan swinging on vines from tree to tree. The more leverage you have, the easier it is to swing to hard-to-reach trees (hard-to-reach jobs).

But how do you create that leverage? Here are three key strategies to help you build momentum and land high-value opportunities.

1. Swing Down to Swing Up: To Get Promoted, Target Companies That Admire Your Current Employer

When you’re looking to make get promoted (perhaps from IC to Team Lead), think about the relative height of the trees you’re swinging between. In this framework, a Team Lead is technically a “higher branch,” but if the next tree is much smaller, you might still have enough leverage to make it.

Target companies that admire your current employer. They’ll naturally view you as bringing valuable experience and insight and put a premium on you relative to someone with the same experience coming from elsewhere.

2. Branch Out Strategically: Specialize to Stand Out

As employees we often focus in growing vertically, which can be tough. Instead, think about how you can grow “out” toward the edges of the tree, by specializing. It’s sometimes easier to climb out on a limb than climb up higher. Specialization creates leverage by distinguishing you from the competition.

Example: Let’s say you decide to specialize in Activation/Onboarding. There might be 10,000 great PMs on the market. But only a handful will position themselves as having that specialization. If I’m a hiring manager considering a PLG go-to-market motion, or I have a PLG motion that’s not firing on all cylinders, you’ve not shot to the top of my list.

Gary Vaynerchuck started as “the wine guy.” Nobody even remember that early positioning anymore. But that early positioning allowed him to stand-out, build a reputation, and then he broadened it from there.

Specializing helps you shorten the distance you need to swing. When you’re known for a skill, you bring a distinct advantage to companies with that pain point.

3. Swing the Shortest Distance: Target Similar Companies and Roles

Whenever possible, optimizing for swinging the shortest distance will give you the most leverage. Target companies or roles that are super-similar, and underscore those similarities in the interview process. In the mind of the hiring manager you’re bringing your current tree closer.

Imagine that you’re applying for a highly-sought-after job at Google. There’ll always be someone smarter, who went to a better college, or worked at a fancier company.

Now let’s say it’s a role on the Google Play Store, covering the EU. And let’s say that you’ve worked for an EU-based company once before, and you’ve worked on mobile app analytics at a BI company. But by underscoring those similarities, you can sitll position yourself as the “best fit.”

During the interview process, ask open-ended questions about the pain points the team is experiencing. Then talk about how you’ve solved similar problems, and connect it back to those two previous roles. You’ve now de-risked your candidacy: of all the candidates, you’re the one most likely to hit the ground running and add value on day 0.

Conclusion

The Tarzan Career Framework is all about creating leverage—using what you already have to reach for the best roles you can swing.

So next time you’re considering a career move, think like Tarzan. Build momentum, create leverage, and swing confidently into the opportunities that await you.

Coding Dojo had hit a wall.

They were a growth stage startup, bootstrapped. A team of 200. They were investing a quarter-million a month on paid ads, had hired a new head of sales, but it wasn’t showing up in revenue.

What happened next is a lesson in how “revenue architecture” - or rethinking data, process, and tools together — can transform your trajectory. I think most marketing teams are too-focused on the upper-funnel. That makes sense - it’s mostly within our control. But a lot of the leverage gets lost in the hand-offs from marketing to SDRs to AEs. By architecting the revenue funnel with a first-principles, aligned approach, we drove significantly more revenue from the same media spend.

Below you’ll find, in great detail, the five specific optimizations we made to our GTM engine that allowed us to double revenue and eventually sell the business.

Do you want to hire Prasid & Airframe Labs? We’ve helped YC-backed startups like Scribd, scale-ups like Booksy, and Fortune 500 companies like SiriusXM. In every case, we’ve helped them grow revenue, fast. And we can do the same for you.

Work with Prasid

The Problem: Stuck in the Growth Plateau

Coding Dojo had a solid product—offering high-ticket online coding courses priced around ~$15K. But despite investing more media spend and expanding the sales org, revenue was flat.

When I first started advising the CEO Richard Wang and mentoring the VP of Marketing Stephen Sinco, it became clear that something else was going on beneath the surface.

The marketing and sales teams seemed to be collaborating well, but in terms of real-time data and process, they were actually operating in silos.

This disconnect is a silent killer of growth.

According to a study by HubSpot, businesses with strong marketing-sales alignment achieve 208% more revenue from their marketing efforts. Not only that: “Organizations with good alignment not only achieve 27% faster three-year profit growth, they also close 38% more deals.”

The Complexity: When Leads Become a Dead End

When I spoke to the VP of Marketing, he told me about the volume of leads they were generating and the number of “application forms” being filled-out.

But here’s the rub: marketing had no visibility into what happened to the leads after that.

Meanwhile, the head of sales complained lead quality was declining, but couldn’t really show in any structured way that the quality had changed.

Another challenge: in this sort of business, the sales cycle could be weeks or months. That’s too long of a feedback loop for marketing to optimize on (we’ll come back to this problem later).

The Solution: The Power of Faster Feedback and Smarter Automation

The answer wasn’t in getting more leads or more applications. It was in identifying the moments that truly mattered in the customer journey, starting to track those moments in a structured way, and move users through those moments faster.

Optimization 1: Putting Structured Data around Key Funnel Moments

When I arrived, the two key KPIs that marketing was measuring were Leads (i.e. email captures) and MQLs (i.e. application form submissions). And sales was moving people through poorly-defined Opportunity stages, and mainly measuring Closed-Won Deals.

The first opportunity: nobody spends $16,000 without have a conversation with a human being. But we weren’t tracking how many conversations we were having in the CRM.

After a prospect submitted an application form, they were invited to book a sales call referred to as as an “interview.”

So our first order of business was to start measuring scheduled interviews and completed interviews.

This sounds so boring and simple in theory but is unbelievably powerful in practice. You have a complex pipeline, with a hand-off from marketing to sales. Before it was a black box. But by adding structured data on how many prospects make it to each stage in the pipeline, you can start to isolate the breakdown and then solve for it. Once it’s in the CRM in a structured way, you can slice and dice it 100 ways (i.e. scheduled-interviews by-channel, by-time-of-day, or by-landing-page, etc.). Suddenly you’ve isolated the problem! It’s so powerful, and I’m always blown away at how few teams do it.

As soon as we implemented this, the problems in the funnel lit up like a christmas tree. As paid spend had increased, the conversion rates from Interviews Scheduled to Interviews Completed was crashing. Prospects from paid channels were ghosting us at a higher rate.

Optimization 2: Creaeting a Feedback Loop for Lead Quality from Sales back to Marketing

The sales team (like every sales team 😉 ) was complaining about the quality of leads. So we worked with them to create a more rigid definition of what constituted a Sales Accepted Lead (SAL).

We introduced 4 qualification questions every rep was required to ask. To be considered a SAL, they had to meet 3 out or 4.

Next, I created a new CRM Opportunity Stages for Interview Scheduled, Interview Completed, and SAL.

To get the sales team using these new stages, we created hygiene dashboards and would chase-down anyone whose interview date had passed whose status hadn’t changed.

The result was a powerful new feedback loop: now instead of finger-pointing between marketing and sales, there was a shared framework for what “qualified leads” meant.

And instead of having to wait 2-12 weeks to know if a lead had become a customer, the marketing team could see within 1-2 weeks of lead creation how many leads had converted to SALs.

I also worked with the marketing team to overhaul their reporting dashboards.

We added Interviews Scheduled, Interviews Completed, and SALs to marketing’s dashboards. Previously, their success was measured by the number of Leads, Applications, Cost per Lead (CPL), and Cost per App.

But I stress-tested the new SAL field. And sure enough, the conversion rate to Customer was dramatically higher when someone was a SAL. So rather than Lead and Cost per Lead, SALs and Cost-per-SAL became the new north-star metrics for marketing.

It took a few months to retool the entire reporting system, but eventually, we could break down CP SAL for every channel (i.e. Paid Search), every campaign (i.e. Competitor Terms), adset (i.e. “General Assembly”), and even individual Google Ads keyword (i.e. “General Assembly tuition”).

Optimization 3: Massive Unlock: Better Data Feedback Loop for Meta Ads

This next bit resulted in its own double-digit improvement in revenue/CAC:

Instead of optimizing for Leads, we were now optimizing our campaigns for SALs. But this was happening through manually adjusting spend. We had a hypothesis: could we train the Meta algorithm to optimize for quality too?

Context: Normally when you drive ad traffic to your site, you’ll fire conversion event back to Meta when someone submits a lead form. Essentially you’re training the algorithm “Hey algo, you scored a point for that lead! Good job, go find more of those.”

But we don’t really care about leads, we care about customers. Why not train our friendly algo for something lower-funnel that’s more highly correlated to customer?

We did this using something called “server-side conversions,” triggering a conversion event for every Interview Scheduled, Interview Completed, and SAL.

There wasn’t enough weekly volume of SALs for the algorithm to learn from, so we told the algo to optimize for Interviews Scheduled.

Next, we designed a proper split-test:

• For 50% of paid spend, we told the algo to optimize for Leads

• For the other 50%, we told the algo to optimize for Interviews Scheduled

We had to run it for 6 weeks to get to stat-sig. But the results was massive: for the same spend, leads went down ~10%, Interviews Scheduled went up ~24%, and Customers increased ~12%.

Optimization 4: Speed-to-Lead to Increase Win-Rates

The upper-funnel was now firing on all cylinders. But we had a new mid-funnel problem emerging.

Prospects would click an ad, fill out the lead form and schedule an Interview all within minutes, but the next available Interview appointment might be a week away. And the further away it was, the worse the Interview show-up rates seemed to be. They’d dropped from 60% to 30%.

We couldn’t hire more sales reps, so we needed to find a way to make sure only the best leads made it to the sales team.

To address this, we implemented Chili Piper, a smart-routing tool that prioritized leads based on their qualification.

We created three distinct “lanes” to manage the flow:

• Fast Lane: Highly qualified leads could request an immediate callback from a sales rep

• Medium Lane: Moderately qualified leads could book an appointment within a few days

• Slow Lane: Lower-quality leads were routed away from sales to a webinar instead

Next, we shifted to a two-step lead form. We added those BANT questions directly into the form. Now we could qualify SALs without talking to a person, and dynamically route SALs to the fast lane and non-SALs elsewhere.

We ran this one one as a split-test too, and found a 20% improvement in No-Show Rates.

Optimization 5: Meeting People “When” They Are

We made another discovery pertaining to show-up rates: we weren’t available “when” customers were thinking about us. This whole time the sales team had been working normal US business hours. But if you looked at the distribution of when leads were coming in, it was quite a lot of nights and weekends, when sales wasn’t working.

You could see this show up in the conversion rates to SALs by day-of-week and time-of-day.

After presenting this data, we managed to come to an agreement with our Director of Sales. We couldn’t expect existing hires to shift their schedules dramatically, but for all new sales hires we’d set expectations they’d need to work nights and weekends. Eventually we moved the entire team to shifts so we’d have coverage 13 hours per day, 7 days a week.

The Results: 2X Revenue Growth and an Acquisition

By improving the hand-off between marketing and sales, introducing automation, and speeding up lead management, Coding Dojo saw a dramatic improvement in revenue:

• Lead-to-SAL conversion rate: Skyrocketed as leads were prioritized and engaged more quickly.

• Time to first call: Moved the average time from Form Submission to Call Completed from 7 days to 4 days.

• Win rates: Increased substantially. Taken together, all these changes resulted in more than doubling our revenue run rate, all while keeping the Customer Acquisition Cost (CAC) steady.

Right around this time, Coding Dojo began entertaining acquisition offers and eventually sold to Perdoceo Education.

Conclusion: More Leads Is the Wrong Answer. Growth Comes from Working the Leads Smarter, Together

What Coding Dojo teaches us is this: a marketing approach that focuses exclusively on upper-funnel is doomed to be inefficient. Todays marketers must be full-funnel.

We formed a cross-functional pod of marketers, sales folks, rev ops, and data analyst. We spent over two years optimizing the customer journey, shipping iteratively week after week.

By rethinking data, process, and tools we transformed Coding Dojo’s trajectory—not through launching new marketing channels or bringing in more leads, but through measuring shared metrics, working the leads smarter, and through marketing and sales alignment.

Did you know Netflix was still shipping DVDs until 2023? One of the biggest mistakes I see startup leaders make: letting perfect be the enemy of the good. Forget perfection—embrace the mess.

Story time:

When it comes to building a successful startup, it’s easy to fall into the “should” trap of thinking that - all the things you “should” be doing. All the plans you “should” be executing flawlessly on.

So let’s examine two stories —one from Netflix and another from Codecademy—that show why it’s better to embracing imperfection.

The Netflix Qwikster Debacle: A Lesson in Navigating Imperfection

❌ Conventional wisdom: Perfect your strategy and then pursue it ruthlessly.

🌱 Reality: You can’t be so narrow-minded — you might need to support multiple strategies for a decade longer than you thought.

In 2011, Netflix wanted to split-off their DVD business into a separate “Qwikster” service so they could focus on the future: streaming.

It made strategic sense and would help them internally and operationally, but customers revolted.

They lost subscribers and their stock price declined by 50%.

Quickly scrapping the idea of Qwikster, Netflix reversed course publicly. But internally stayed focused on streaming.

CEO Reed Hastings admitted:

“Sometimes, the thing that makes you great, your speed, can trip you up… we need to be more thoughtful as we move.”

Long-term the shift to streaming was correct, but the market in 2011 simply wasn’t ready.

They had to live with the mess and keep supporting the DVD business for another 12 years before finally sunsetting it in 2023.

Overplanning at Codecademy: Why Momentum Beats Perfection

❌ Conventional wisdom: Run quarterly and annual planning processes. Create cascading OKRs that ladder-up elegantly from team goals to department goals to company goals.

🌱 Reality: Annual plans are too long - things change too fast in a startup. And it can easily take weeks to perfect those cascading OKRs: time you’re not spending shipping. Meanwhile quarters are too short to truly ideate, adjust teams, and still make substantive progress.

At Codecademy, I remember spending 3 feverish weeks on annual planning.

We built company level OKRs that cascaded down to teams. Every department spent time horse-trading to get each other’s dependencies added to each others OKRs.

When we finally rolled-out the cross-functional teams that would pursue each big objective, we were already into February.

OKR best practices say leadership should define the “desired outcome” and let teams figure out “how we get there.”

That means each cross-functional team now needed to run their own planning process to ideate, gather context and data on their area, and talk to customers, and write a roadmap for how they get there.

By the time they started picking up momentum actually shipping, it was the end of March. And we started rejiggering OKRs and adjusting teams all over again.

No bueno. 🙅‍♂️ 🌮

Too much planning can kill momentum.

Instead of such a rigorous process, be okay with some mess.
Write six month plans instead of annual plans. Long enough for teams to build momentum but short enough to adapt.

Keep teams stable for at least six months so they can build-up context and pick up momentum, even if it’s sub-optimal. As a leader this might feel like you did a slap shod job, but people are resilient and it’s better to be moving than at a stand-still waiting for the plan to be perfect.

"You can’t steer a parked car." Taking action and making adjustments along the way beats being perfectly-aligned before moving.

The Power of Imperfect Action: Keep Moving Forward

Both Netflix and Codecademy learned that the some motion beats perfect direction.

In a startup, flexibility and momentum are your greatest assets.

If you worked in startups from 2009 to 2015, you’ll know things were tough. Maybe tougher than now. I did a LOT of job-hunting.

And since then, I've also done a lot of career coaching for others. Here are some of my favorite lesser-known wisdom-nuggets to network like the best.

1. Shift Your Focus to Helping Others As a Way to Overcome Networking Anxiety

Personally, I’ve always been intimidated by networking events. I'd often sink into self-consciousness. But a mindset shift that helped was to shift my focus from "attendee" to "helper."

In Never Eat Alone, Keith Ferrazzi suggests that when meeting someone new, skip the small talk.

Instead, ask what they’re passionate about. When they answer, think about how you can help them. And then offer that help.

2. Take Control of Key Communications Infrastructure, Then Leverage It to Your Advantage

During his 1973 military coup, General Augusto Pinochet of Chile prioritized quickly taking control of the national TV station. But why a TV station? There’s no military importance.

Pinochet knew that if you control the airwaves, you can shape the narrative. And as for the airport? Well, that’s your golden ticket to decide who gets to join the party—or who has to leave.

Now, I’m not suggesting you overthrow a government (let’s keep this legal, folks). But there’s a lesson here: if you can become connected to key social infrastructure, you have access to opportunities that others won’t.

That's why post-pandemic I decided to start hosting startup marketing meetups. I was part of a Slack community that hadn't met IRL in 3 years, so I took it upon myself to host one myself.

At a minimum, this completely changed my mindset at the event. Instead of being an attendee, I was now the host. And I was so focused on if everyone else was okay that I forgot my own social anxiety.

But the benefits have gone further: folks from that community have referred clients my way, I’m often invited to other tech and VC events, and I now feel a sense of belonging in NYC's startup community.

Another great example is my friend Jameel who graduated from MIT and started working at Microsoft. Jameel volunteered to help Microsoft’s MIT recruiter with her on-campus recruiting. When Jameel visited campus, he showed the recruiter he was still tied into clubs and the greek system by helping to drive turnout for recruiting events. Soon-enough Jameel was the recruiter’s go-to person and he was getting flown-out to Boston.

On the other side of this hiring marketplace was current MIT students. They wanted jobs, and he was helpful in advising them and connecting them. Whether they joined Microsoft or someplace else, Jameel’s network of MIT alumni working in tech exploded.

By being helpful to both sides, Jameel put himself at the center of a key piece of infrastructure: the MIT <> Microsoft hiring pipeline. He got free trips to visit friends in Boston, an expense account to entertain them, and a powerful alumni network.

3. To Build Meaningful Friendships, Invite Bar-Friends to An After-Party

In high school in Dallas, TX, I was a self-proclaimed nerd and spent weekends with my best friends talking about Star Trek and competing over SAT scores. After college, three of those friends moved back to Dallas. And that first year back was pretty rough.

They’d go out to bars. They might see an acquaintance out, and have a friendly chat. They might even get introduced to someone new. But there was no good way to convert these friendly acquaintances into real friendships.

The answer, my three friends taught me, was SGI.

Small. Group. Interaction.

They started inviting folks out for a pre-game at their apartment. Or when the bars were closing, they’d propose going to Big Wong’s for late-night chinese. On the way, they’d carpool.

This pre- or post-bar “Small Group Interaction” changed the psychology of the night in an important but subtle way. Now, instead of “I saw them at the bar.” The night became “we all went out to the bar together.”

This pre- and after- framework was a game-changer. One of them met his wife that year in Dallas, and they just celebrated their 10-year anniversary.

4. Personal Branding Widens the Upper-Funnel of Your Career Opportunities

Naval Ravikant had an equation for Luck Surface Area. The idea is that so much of success is luck. But that you can increase your surface area for luck by having more access to opportunities. Naval uses the example of literally starting multiple businesses to increase your surface area of luck.

But a “higher-funnel” approach might be to increase the number of opportunities you have access to. Cody Sanchez says “Be easy to find, but hard to reach.” She runs an online program for people who want to buy or own businesses. So she pumps out free content on Twitter, LinkedIn, YouTube, and elsewhere so that when someone is finally starting to think about a business, her program is the first one they think of.

5. The Average Job Tenure Continues to Decline: So Always Be Closing

Final thought.

Having a network isn’t enough. You need to be using it and putting it out there that you're open to opportunities.

The average tenure for American workers is less than 4 years and dropping. We'll hold on average 12 jobs in our lifetime — up from 10 a decade ago!

I used to think: “I know people, and people know me, so when I need a job, I’ll just ask around and find one.” But with companies showing less and less loyalty to their employees, and tenures shrinking, you should be testing your market value often.

As a consultant, at least 10% of our engagements have come from situations where initially it wasn't a fit, but we reconnected months or years later.

The truth is that you need to be constantly evaluating your market value, constantly be investing in yourself, and constantly be open to new opportunities, so that the day you actually want to close a deal, you’re already 80% of the way there. In effect: always be closing.

So, there you have it—my roadmap to building a powerful network. Start by paying it forward and giving more than you take. Then, take charge of the “infrastructure” around you, whether it’s organizing events or volunteering your skills. Remember, real connections often come from small group interactions, so don’t overlook those pre-game drinks or after-dinner coffee chats. Personal branding is your megaphone; use it to widen your reach and be top-of-mind for new opportunities. And, most importantly, always be open to possibilities.

Now, go out there and put these strategies into practice. You’ll not only grow your network but also turn it into a true asset that works for you. Here’s to building connections that last and seizing the opportunities that come your way.