š§ Real PM Case Study, Week 4
This one shows up in interviews more than almost any other scenario and most candidates fumble it.
You're the PM for a B2B SaaS project management tool.
Your product has a free tier and a paid tier, and growth has been solid.
Then the data lands on your desk: free-to-paid conversion dropped 22% over the last 60 days.
Support tickets are flat. NPS hasn't moved. Users aren't complaining.
They're just not converting.
The funnel looks healthy on the surface. But something changed. And your VP of Product wants a plan.
My team had capacity for ONE initiative.
Here's what was on the table:
A) Paywall Repositioning Move the paywall trigger earlier in the user journey, surfacing the upgrade prompt at the moment of highest intent - like when a user tries to invite their third team member or set up an automation. Bet: users aren't converting because they reach the limit at the wrong moment, not because they don't see value.
B) Activation Audit Run a full audit of what free users do (and don't do) in their first 14 days, then redesign the onboarding flow to drive them toward the "aha moment" faster - the action most correlated with paid conversion. Bet: users are churning before they've felt the product's core value, so no paywall optimization will fix it.
C) Conversion Nurture Campaign Build a targeted in-app + email sequence for free users who are active but haven't converted after 30 days - personalized by use case, with a time-limited incentive to upgrade. Bet: the intent is there, but users need a nudge and a reason to act now.
Here's what I want to see in your answer:
- Which option do you pick, and why?
- What's the one assumption your entire decision rests on?
- What would you measure in the first 30 days to know if it's working?
Drop your answer below. I'll reply to every single one with real feedback.
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š§ Real PM Case Study, Week 4
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