How Front Succeeded with Its Partner Motion | Cailen DSa (Early GTM at Dropbox, Box, and Front)
An oft-overlooked channel, partnerships can be a high-ROI part of your early GTM strategy.
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:
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.
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.
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.