Replace the free trial with a short paid pilot, or an annual contract with an opt-out, so "customer" is the default.
Clever, the education software company, never offered free trials. Co-founder Tyler Bosmeny sold annual agreements to the learning-software companies that paid for it, with an opt-out if they were not happy in the first 30 or 60 days. He argued that a free trial gives you none of what you need from a new customer: commitment, validation and revenue (Stanford CS183B lecture, 2014; Y Combinator Startup School, 2018).
By 2020 Clever served half of US K-12 students and 65% of US school districts, and Kahoot! bought it in 2021 for up to $500 million including performance payments (Kahoot!, 6 May 2021). Clever was free to schools, and its exit cannot be put down to its contract terms alone.
B2B services and SaaS closing first contracts, and anyone whose free trials rarely convert.
A pilot only means something if the customer has paid for it and agreed what success looks like. Y Combinator's Tom Blomfield sets out the mechanics: price the pilot at an amount the champion can approve personally so it skips procurement, book the post-pilot review before the pilot starts, check in every couple of days, and convert into a recurring contract with a 30 or 60-day opt-out (Startup School, August 2025).
Even serious pilots stall: in Madrona's survey of 150 senior leaders at enterprises with more than $500 million in revenue, 83% said fewer than half their AI pilots became scaled deployments in the past 12 months, mostly because of integration and security hurdles (Madrona, August 2026).
Self-reported. Tyler Bosmeny's and Tom Blomfield's Y Combinator talks (2014 to 2025). Reported. Kahoot!'s acquisition of Clever (May 2021). Vendor. Madrona's enterprise AI survey (August 2026).
Cost to test. No cash cost: the pilot pays you. The cost is the risk of a smaller first deal.
Kill it if after five proposals no prospect will pay for a pilot, which usually means the problem is not urgent enough.
The pilot has to deliver quickly, so pick the narrowest problem that hurts. Be careful reporting revenue still inside an opt-out period as recurring. Some large buyers have procurement rules that block paid pilots, so ask early.
Trigger Outreach, Built For You, The Roundtable Series
A 30-minute call first. If it fits, two calls in one week and a written growth plan you keep.