Chalk.com was making $3,000 a year charging individual teachers $30 each. Then a school in Texas requested 72 licenses in 24 hours - and that one phone call revealed B2B product-market fit. The real buyers were schools and districts, not individual teachers. That SaaS product-market fit insight changed everything. Ryan McKay-Fleming and his co-founder William built the first version at a kitchen table on a hunch, without talking to a single teacher. They made the product free for teachers to drive B2B PMF through word-of-mouth adoption, then sold premium collaboration features to schools. The product-market fit B2B strategy grew Chalk.com to 100,000 users. Ryan shares how two University of Waterloo students navigated education's seasonal sales cycles, why domain knowledge finds you when you need it, and what happens when you build for an industry you know nothing about. 🔑 Key Lessons 🎯 Your real buyer may not be your user for B2B product-market fit: Chalk.com struggled selling to teachers at $30/year but found PMF when a school wanted 72 licenses. The users were teachers but the buyers with budgets were schools and districts. 📉 Building without validation delays B2B product-market fit: Ryan and William built on a hunch without talking to a single teacher. The product combined day planning and lesson planning, doing neither well. 💰 Freemium can unlock B2B product-market fit at scale: Making the product free for individual teachers drove 100,000 signups through pure word of mouth with zero advertising spend. Revenue came from premium school plans. 🧠 Domain knowledge finds you when you need it: Ryan says advice and knowledge appear when you are ready for them. Chalk.com restructured its sales process years in using information that always existed. 🏢 Seasonal sales cycles require funding bridges: Education buying happens in spring and conversations start in fall, leaving months with no new revenue. This gap is why Chalk.com raised $500K. Chapters Introduction How Ryan and William came up with the idea Building the first product at a kitchen table Was it a business or just a project The first version of Plan Board Why they skipped validation entirely Discovering the product missed what teachers wanted Getting the first customer at a pitch competition Charging teachers $30/year and making only $3K The freemium pivot and business model The phone call that changed everything - 72 licenses How the school district model works Marketing channels and word of mouth growth Surprises from not doing customer development Education market fragmentation Seasonal sales cycles in education Building for an industry you know nothing about Tech stack - Ruby on Rails and React Lightning round Resources Full show notes: https://saasclub.io/108 Join 5,000+ SaaS founders: https://saasclub.io/email