Alejandro Rioja Is Building the Club Operating System He Wished Existed

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 built 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 live in one place, but the part 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, instead of leaving a dashboard to interpret.

“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.”

Unlike most founders building software for an industry from the outside, Rioja 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 as a pilot bolted onto older tools, and has posted roughly a 25% revenue increase since making the switch — credit Rioja gives as much to the morning recommendations as to the booking flow itself.

His ambitions 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.’”

To learn more about Courtlines, visit courtlines.com. More on Alejandro Rioja at alejandrorioja.com.