kenny sandon

proprise (yc s23) · 2024–2026

cutting churn and rebuilding onboarding

Monthly churn down more than 80%. Weekly active users up 64% in the three months after the Hot Spots launch. Onboarding cut from 48 hours of hands-on work to 2.

We were losing 3–4 customers a month and cancellation calls never told us why. So instead I dug through PostHog data and session replays, and interviewed the customers who stayed. Two problems kept coming up that nobody had mentioned on their way out: weak data exports and a frustrating map. We fixed both. Then a survey of every customer pointed at the feature people loved most, finding promising sub-markets, and we relaunched it as Hot Spots.

I was every customer's primary contact: about 200 users across 50+ firms. When something broke, my rule was to get the affected customer on the phone fast and tell them we were on it.

  • Onboarding rebuilt with Claude skills that read each customer's Excel model: 48 hours of hands-on work down to 2
  • Trained every new team live, and tested that they could run the product on their own before I stepped back
  • Support response under 30 minutes, on every channel
  • Hundreds of demos, onboardings, and retraining sessions
  • Onboarded Public Storage's two teams separately, since acquisitions and development use the product for different jobs