The Pricing Page We Changed Six Times (and the One Number That Mattered)
Tiers, toggles, annual discounts, a free plan and back again. What two years of pricing experiments actually taught us.
Founders love to tinker with pricing pages. I know because I changed ours six times in two years, each time convinced this version would unlock growth. Here is the honest history, with the numbers we saw.
Version 1: One plan, $49 a month
Simple and fast to launch. Conversion from trial to paid was 9 percent. Our problem was that tiny solo users and 40-person teams paid the same price. We were leaving serious money on the table with the bigger accounts.
Version 2: Three tiers
We introduced Starter, Team and Business at $29, $79 and $199. Classic stuff. Trial conversion barely moved, but average revenue per account rose about 35 percent. Good change. We should have stopped tinkering here for a while.
Version 3: A free plan
A competitor launched a free tier and we panicked. Signups tripled within a month. Paid conversion fell to under 3 percent, and our support queue doubled with free users asking detailed questions. Eight months later, free users made up 81 percent of accounts and 0 percent of revenue.
Version 4: Annual discount toggle
We added a toggle offering two months free for annual billing. About 28 percent of new customers chose annual. This one was genuinely helpful for cash flow and lowered churn, because people who prepay for a year tend to stick around.
Version 5: Usage-based pricing
We tried charging per active user. In theory it was fairer. In practice, customers hated not knowing their bill in advance, and our sales calls turned into maths lessons. We reverted after one quarter.
Version 6: Back to three tiers, no free plan
We replaced the free plan with a 14-day trial and kept the annual toggle. Signups dropped by half. Revenue grew faster than at any point before.
The one number that mattered
Through all six versions, the metric that best predicted our health was not signups, conversion or even revenue. It was net revenue retention: how much revenue an existing cohort produced a year later, including upgrades and churn.
When pricing nudged customers toward plans that grew with them, retention climbed above 110 percent, meaning a cohort was worth more each year without any new sales. When pricing attracted the wrong customers, as the free plan did, retention sank and nothing else could compensate.
What I would tell a founder today
- Change pricing rarely, and give each version at least a full quarter.
- Watch retention by cohort, not just conversion on the page.
- A free plan is a marketing decision, not a pricing one. Budget for it like one.
- Never copy a competitor's pricing without knowing their margins.
Your pricing page does not just set a price. It decides which customers you get.
We got that lesson the expensive way. You do not have to.
Cover: Photo by Angèle Kamp on Unsplash.
