What's the pricing mistake you'd go back and fix first if you could?
We launched with seat-based pricing because that's what everyone else in our category did. Seemed logical. Our free users were mostly solo operators who would never add a seat. They hit the paywall, saw 'add team members,' thought it wasn't for them, and churned quietly. No rage. No feedback. Just gone.
Switched to usage-based. Conversion rate doubled in a quarter.
The hard lesson: your pricing structure tells users who the product is for. If the upgrade logic doesn't match how free users are already getting value, you're not solving a conversion problem. You're solving a product-market fit problem disguised as a pricing problem. Those are very different things to fix, and confusing them will waste you a year of experiments that go nowhere.