The Cohort Challenge

Good morning! Now that so many of you are tuning in every Sunday, let's get to know one another. How about we start with an icebreaker? I picked this one up from a founders event I attended recently, run by the folks over at Cosmic Collective: How did you make your first dollar??(any and all currencies count, I just default to my home country Canadian dollar when I talk ??)

For me, it goes way back to 2nd grade, when my best friend and I spent afternoons making colourful friendship bracelets... You know the ones made out of carefully knotted embroidery thread? We sold them to classmates and used the profits to buy even more craft supplies, expanding our little "business". It was a simple venture, but looking back, it taught me the basics of creating something with value and growing from there.

From first dollar to first cohort

That memory got me thinking about another first—our earliest ProdPad customers. Some of them are still with us today, 10+ years later (a huge thank you to you awesome early adopters!).

Early adopters are a special breed. They're willing to put up with your scrappy MVP because they believe in what you’re building (did you know that Simon Cast and I built ProdPad ourselves? I had to learn some pretty hacky JQuery to get it out the door!) Your early customers stick with you through growing pains because they can see the long-term vision.

But when you're new, you only have one cohort—your current users. They don't have years of experience with your product, so you can focus on their immediate needs and learn alongside them.

Balancing old and new cohorts

As you grow, it gets trickier. You're no longer just serving one group of users; you have multiple cohorts. Your early adopters have become seasoned users—they're asking for advanced functionality and finding workarounds faster than you can build solutions. At the same time, you're constantly bringing in new users, who need a simple, intuitive onboarding experience.

Managing this balance is challenging. You need to keep things simple for newcomers while delivering deeper functionality for your long-time users. If you're not careful, this can result in a slump! Friction in onboarding results in less conversion and growth, slowing down your business just as it takes off. It did for us, a few years into our growth story. We had an overcomplicated product and lost sight of the simple onboarding that we previously offered to our earliest cohort. It took months for us to spot and correct this, but we did, through a series of experiments and tight focus on the problem. This is where our magically extending free trial comes from, among other I actually spoke about this at the time, this "Power of Product Focus", as the efforts we put in resulted in us taking off and getting to where we are today (the rest is history, they say!)

But ultimately, if I've learned anything from this age old problem that hits every growing SaaS business, it's encapsulated in these tips:

Segment your users: Don’t treat everyone the same. Understand where each group stands and tailor your communication and feature rollouts accordingly.

Example: At ProdPad, we use segmentation to communicate effectively with different user groups. For example, when we introduce a new feature like Objectives and Key Results, we tailored the message for advanced users by focusing on how they can integrate OKRs into their existing workflows. Meanwhile, for newer users, we focused on a simpler onboarding message, guiding them on how to set their first objective and align their roadmap around it.

Optimize onboarding: Make sure new users don't feel overwhelmed by advanced features. Introduce them to the product progressively.

Example: ProdPad's onboarding guides users step-by-step through the core features first—like adding ideas and building a Now-Next-Later roadmap—without immediately diving into more advanced functionality like integrations or automations. We also use in-app tooltips and contextual help to offer deeper explanations when users are ready for them, making sure the learning curve feels gradual.

Create learning paths: Help your experienced users discover new features and push the limits of your product with advanced tutorials or case studies.

Example: For seasoned users who have been with ProdPad for years, we offer in-depth webinars and case studies that show how companies use more advanced tools like Signals, CoPilot, or integrations with Jira and Slack. This helps them uncover new ways to maximize ProdPad’s capabilities, like automating workflows or refining their product strategy.

Communicate clearly: Keep everyone informed about changes. Explain why new features are valuable for different user groups.

Example: As we launch CoPilot, our AI tool, we're rolling it out gradually, first letting advanced users try it out in a beta phase (happening now if any existing users want in!). We're using this time to gather feedback and explain how the tool helps power users by taking on repetitive tasks. For newer users, we're framing it in the launch as a helpful guide that reduces the overwhelm of managing feedback and roadmaps, highlighting how it could accelerate their learning process.

Keep the MVP clear: Don't neglect the core product experience. Revisit it regularly to make sure it stays simple and valuable. Your job isn't to constantly add new features, but to run experiments—sometimes those experiments should be to remove features!

Example: At ProdPad, we periodically revisit the basics, making sure that adding ideas, building roadmaps, and collecting feedback remains intuitive and easy. Even as we’ve layered on advanced tools, we’ve kept our focus on making sure new users can quickly grasp the fundamentals and start getting value from day one without feeling like they need to learn everything at once. Tools like Mixpanel are your friend here! Use a mix of quantitative/behavioural as well as qualitative feedback to get a sense of what's being used and what's actually adding value.

Your turn

Now, back to that icebreaker—how did you make your first dollar? Jump into the comments and let me know! I’d love to hear your stories. And if you're grappling with multiple cohorts, old and new, let's talk about how that's going, what you've done to cross that chasm.