How Slack Pivoted from Freemium to Free Trial to Fuel Revenue Growth | Q&A Shikha Kaiwar (Product Marketing & Growth Leader)
Shikha shares how Slack became one of the most successful PLG companies in history, running complex monetization experiments in the run-up to their IPO.
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:
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.
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.
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.
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.