How Pickleheads Turned a Free App Into Usage-Based Revenue

Case study·Aug 24, 2026

Pickleheads is the number one mobile app for pickleball. Players use it to find and organize games, round robins, leagues, and tournaments, from a weekly neighborhood game to facilities running full schedules on the platform.

Max Ade, founder of Pickleheads, talked with us about the shift from a free consumer app to paid subscriptions, and how to make that shift without stalling a product that grows on network effects.

Limits instead of paywalls

Pickleheads ran free for three years with no monetization plan. When the team decided it could not keep running on investor dollars and sponsorships, it chose subscriptions. The catch: the app grows because players invite other players, so gating features outright would cut off growth. People needed free access to core features and a taste of advanced ones before paying. Usage limits made that model possible.

None of what we do from a pricing standpoint would have been possible without Schematic. We wouldn't have been able to do things like limit the number of round robins you can run in a given month. We would have just said you can only run round robins on a paid plan, and a lot of people would have been out of here.

Pricing changed in the first week

Subscriptions launched in mid-December, which meant putting features behind a paywall that organizers already used every week. The team got on Zoom calls with customers, collected a wave of feedback, and changed the pricing model within the first week. One change stuck: small groups could not qualify for a free organizer subscription, so Pickleheads reworked the rule. That rework became the center of the whole strategy. Organizers and facilities get everything free when all of their players subscribe, whether that is five players or five hundred.

When you're first setting it up, you do think of it as building a feature. And it's not really a feature, it's more like a product that you have to maintain and iterate on.

The source of truth for plans and entitlements

Max wears about ten hats, and most of his Schematic usage now runs through Claude and the Schematic MCP. His Claude does the first round of customer support, looks up plan information, and pulls usage logs during bug investigations. When a customer says they never ran ten round robins this month, he can check their billing period and see exactly when each event fired.

We do most of our work now starting in Claude. I spend very little time even in the Schematic UI. Just having a way to get in there and find information is incredibly valuable.

Overrides keep customers happy

Pickleheads runs on a small team with a small dev team, so exceptions cannot depend on engineers. When someone burns through their round robin limit on a test, Max raises their limit for the month himself, with an expiration date, and explains how the limits work. He can also make an override permanent for a customer he wants to reward.

Anytime somebody is frustrated with a limit on their plan, I'll give them more that month and explain the limits again. It's huge for customer support because I would have no way of making those things right otherwise.

Max's advice to other founders comes from watching a fellow Atlanta founder run pricing experiment after pricing experiment: pricing is not something you set and forget. Schematic is what lets Pickleheads change things in one place, migrate people between plans, and run those experiments without building the machinery first.

We've obviously worked with a lot of different SaaS providers across the business, and you guys are by far the most responsive in terms of feature requests and support.

Watch the full conversation: How Pickleheads Turned a Free App Into Usage-Based Revenue.