Pricing Page Autopsy: The A/B Test That 2x'd Close Rates

A $280K ARR, three-person B2B SaaS team ran on gut-feel pricing for fourteen months while trial-to-paid conversion sat at 3.1% — less than half the ChartMogul 2026 median of 8.9% — until a first-ever MRR dip in month fifteen forced a systematic approach to pricing experimentation. This is the Wednesday episode for Week 20 of 2026. - How a tier restructure moved one feature down one level and lifted page-to-trial conversion by 18%, from 3.1% to 3.7%, on five weeks of thin but sufficient traffic - Why flipping the billing toggle default from monthly to annual pushed annual plan mix from 15% to 41% of new sign-ups in five weeks - How the tier restructure drove a 37% churn reduction by aligning feature packaging with solo-operator needs and opening meaningful expansion ARR growth in the following six months - Why the founder rejected usage-based overages to protect ARR predictability, and how a homegrown billing system collapsed under three concurrent plan versions before a three-week hard-stop fix restored order Guest: founder and CEO, ARR at time of recording $280K, B2B SaaS. If this episode changes how you think about pricing and growth, share it with one founder who needs it and subscribe on YouTube or your podcast app.