Alejandro Rioja spent years running Pickleland, his indoor pickleball facility in Austin, before deciding the biggest problem in his business wasn’t pickleball at all — it was the software running it.
“Every booking system out there is the same — CRUD screens, a dashboard, good luck,” Rioja says. “None of it’s AI-first. I wanted something that runs itself and gets better on its own, not something I babysit.”
That frustration became Courtlines, a club operating system Rioja is now building for racquet and court-sport facilities — pickleball, tennis, padel, squash, badminton, with room to extend into adjacent spaces like volleyball and CrossFit. Booking, memberships, point-of-sale, and scheduling, all in one place.
Unlike most software founders building for an industry from the outside, Rioja’s been inside this one the whole time. “I wasn’t guessing at the pain points — I was living them,” he says. “Different kind of insight when you’re the operator, not just building software for one.”
The feature he keeps coming back to isn’t a screen, it’s a routine. Every morning, Courtlines’ AI advisor reviews a club’s numbers and tells the operator what to actually do about them.
“Favorite part’s the AI advisor — every morning it tells you what to actually do with your numbers instead of just showing you a dashboard,” he says. “Software that improves itself, not software you babysit.”
Pickleland runs on Courtlines end-to-end, not as a pilot bolted onto its old tools, and has seen roughly a 25% revenue increase since making the switch — a number Rioja credits as much to the morning recommendations as to the booking flow itself.
His ambitions for Courtlines go past racquet sports. “Short term, club OS for racquet sports,” he says. “Long term I want this running any small business that lives on time slots and memberships — gyms, salons, whatever. Started with courts because that’s the world I know. But the itch was never just pickleball, it’s ‘why is this software so dumb.’”
It tracks with how he talks about Pickleland itself, which he calls the hardest business he’s built. “High fixed costs, hands-on customers, nowhere to hide,” he says. “Building the software myself wasn’t a side project, it was the only way to get something that fit how we actually run things.” He’s spent the past year going deep on AI automation more broadly, and Courtlines is where that interest collided with his day job. “The advisor’s basically me handing other operators the same leverage.”
Courtlines is early. Pickleland is the proof of concept; the real test is whether it works as well for clubs Rioja doesn’t personally run.
