What worked pricing with one simple annual plan

We had monthly, annual, and a fake "enterprise" tier that confused everyone. Support questions were mostly "which plan do I need?" Conversion was flat. We collapsed to one annual price with a 14-day trial. Monthly stayed hidden unless someone asked. Checkout completion went up because the decision was binary: try it or don't. Annual cash upfront also changed how we thought about support—we could afford to help customers succeed instead of churning them monthly. Simpler pricing was a positioning move as much as a UX fix.