GETTING STARTED WITH USAGE-BASED PRICING

Summary from the TLDR Founders newsletter

AI features create a pricing nightmare because some customers barely touch them while others 10x their usage overnight. Kyle Hart built Toast's pricing playbook from $0 to $100M ARR and says customers claim they want usage-based pricing but actually hate the variability. His approach is similar to how you'd test a new feature. First, audit what you have - which features do reps discount most? What are customers actually using? Then, form 2-3 mock pricing pages to test in real sales calls. Slowly build your conviction over time before making the swap.