400% subscription conversion in six months

The problem

Conversion from free to paid sat well below benchmark for a freemium product with Doodle's top-of-funnel. Two things were structurally wrong. There was a free trial sitting inside a freemium product, which asked people to start a trial of something they already had a version of. And the only way to pay was a twelve-month commitment, on a product many people needed intensely for three weeks and then not at all.

What we did

• Killed the free trial. Conversion went up 15%.
• Built monthly plans. Aligned billing, finance, marketing, product and the exec team on the rationale and the cannibalisation risk before a line of code got written, because the finance objection to monthly pricing is always the same one and it's cheaper to have that argument early.
• A/B tested three monthly price points against the annual control, and picked on the balance of conversion, retention and MRR rather than conversion alone.
• Tracked the cohorts for a full year on retention and NPS, so the decision could be reversed if the smaller commitment turned out to buy worse customers. It didn't.
• Ran 19 experiments on the free/paid feature boundary. Thirteen shipped.

The call I had to make

We mocked up an ad-free tier at three price points and sold it to real users, who quietly got full premium instead. Conversion went up. It also would have cannibalised the plan above it and dropped MRR. So we killed a tier that tested well, on a spreadsheet, and saved months of engineering.

Impact

• Subscription conversion up ~400% in six months
• Monthly plans alone: conversion doubled, MRR +260%
• Free trial removal: +15% conversion
• MRR up ~450% across the period
• Retention and NPS held across a full renewal cycle