How Pickleheads Turned a Free App Into Usage-Based Revenue

Max, founder of Pickleheads, a pickleball app, switched from free to usage-based pricing after three years. He built an entitlement system with Schematic that lets non-technical staff grant overrides and run pricing experiments. The platform integrates with Claude AI to handle customer support and resolve issues like promo-code bugs within a day.
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I'm Max. I'm the founder of Pickleheads. We are the number one mobile app for pickleball. So we help players find and organize games, round robins, leagues, tournaments, that kind of thing. And day to day, I'm a PM. So I spend my entire day pretty much making linear tickets, QAing changes, and talking to customers. I wear about 10 different hats, and it's great. So we started as a free consumer app, and you know one of the one of the reasons we founded the company is we were just really excited about pickleball, and we saw an opportunity to create a product. in a fast-growing market, but we had no idea how we were going to monetize it. And when we got 3 years in, we sort of hit a wall and said, enough's enough. We can't keep running on investor dollars and sponsorships. We need to get serious about how we're going to try and monetize it. None of what we do from a pricing standpoint would've been possible without Schematic because we wouldn't have been able to Do things like limit the number of round robins you can run in a given month, right? We would've just said, oh, you can only run round robins if you were on a paid plan. And a lot of people would, would've been outta here. We didn't want to re— we didn't want to build this whole entitlement system with usage-based pricing. And then we wanted the non-technical members on our team to be able to access things, right? Like, as a— when I'm doing customer support, I want to be able to go in and give somebody an override on something. That's really important to us because we have a very small team, small dev team. We have a lot that we're trying to do with our product. And so the last thing I want to do is have to constantly be going to the dev team and tapping them on the shoulder. I think of it as the source of truth for plans and entitlements. And so we, the way I use it the most is I have it hooked up to my Claude and my Claude is also does the first round on customer support too. So it'll get an email from somebody, it'll be able to look up their plan information. And then the way that I end up using it the most is is when my Claude is doing an investigation into, you know, a potential bug or whatnot, it'll go in, ask Schematic a lot of questions about different things, and then we'll figure it out from there. An override is, let's say there's a limit, we have a limit for a number of round robins per month, so you can get 10 on the Pro plan. Someone might write in and be frustrated about the limit and I might say, hey, I can give you 5 additional this month. And I can go in and say, let's up that to 15 and it'll expire at the end of this month. When you're first setting it up, you do think of it as like I'm building a feature and it's not really a feature. It's more like a product that you have to maintain and iterate on. So that's why a schematic is really useful because we can change things in one place that cascade. to everyone. We can migrate people from an old plan to a new plan. We can do usage-based pricing. Like all the things that would have to be built out manually in order to run different pricing experiments, it's all kind of, it all kind of comes out of the box with Schematic. The customer support is fantastic. I mean, like it's outrageously good. I mean, I'll just give you an example yesterday. we ran into an issue. We were trying to apply promo codes dynamically on the checkout component. And by the end of the day, there was a new version of the component we could install that solved the problem. So the response time, not only to answering questions, but also to feature requests, is really impressive. That's one thing that I mean, I've worked, we've obviously worked with a lot of different SaaS providers across the business and like you guys are by far the most responsive in terms of feature requests and support.
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