Clarity on what to do first

The problem

A bootstrapped, founder-led company in revenue enablement had a compelling new AI product vision: measure sales skills from real calls and tie them to revenue. It also had nine adjacent opportunities competing for attention, and a retention problem the founder considered the company’s biggest risk.

Everything felt urgent, and nothing had an order. The founder personally made every product call. Sprint planning and backlog grooming ran as one unstructured meeting, and decisions were made on conviction rather than evidence.

What I did

• Found the real retention drivers. I set out eight retention hypotheses and tested them against recorded customer calls, account-health data, and months of field-team feedback. The strongest signal was cohesive team usage, not raw logins. I also found a risk factor the health model couldn’t see: whether a services consultant was embedded in the account.
• Set the order of work. I built a roadmap ordered by what each step makes possible, not by feature priority, and named the one thing to do first. The founders closed four blocking decisions that had been open for months.
• Installed a product rhythm. A weekly cycle of hypothesis → prioritize → design → build replaced the blended meeting. Customer calls now start with a stated hypothesis.
• Coached the next product leader. I coached a principal designer through the move into product management: roadmap, discovery interviews, prioritization, and running the weekly product meeting.

What changed

• The team narrowed nine bets to one platform thesis and is now shipping the strategy we set.
• The founder moved from making every product call to staying informed while the team drives.
• Customer evidence became a company-wide habit, with call clips shared at the weekly all-hands.
• The team asked customers the question they’d been avoiding and got their first clear answer on how they differ from the category leader.