Alejandro Rioja didn’t set out to become a software founder. He set out to run a pickleball facility, and Pickleland — his indoor court operation in Austin — turned into the hardest business he’s built. High fixed costs, hands-on customers, no room to coast. What broke his patience wasn’t the pickleball, it was the software running the business underneath 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 complaint became Courtlines, a club operating system Rioja built for racquet and court-sport facilities — pickleball, tennis, padel, squash, badminton, with room to stretch into volleyball and CrossFit. Booking, memberships, point-of-sale, and scheduling all live in one place, which isn’t the differentiated part. The differentiated part shows up every morning: an AI advisor reviews a club’s numbers overnight and hands the operator specific, ranked actions — reopen this time slot, adjust that price, reach out to these lapsed members — instead of a dashboard he has to interpret himself.
“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.”
What separates Rioja from most founders building club software is that he isn’t guessing at the workflow from the outside. He was the customer first. “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.” Pickleland runs on Courtlines end-to-end — not a pilot, not a demo account — and has posted roughly a 25% revenue increase since the switch, a number he credits as much to the morning recommendations as to the booking flow itself.
The roadmap doesn’t stop at racquet sports. “Short term, club OS for racquet sports,” Rioja 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.’”
Courtlines is early, and Rioja knows it. Pickleland is the proof of concept. The real test is whether an AI advisor built on one operator’s data holds up across clubs he’s never set foot in.
Follow Courtlines: courtlines.com · Alejandro Rioja: alejandrorioja.com