Pickleheads Scores $2.5M to Elevate Pickleball’s On-Court Experience

Pickleheads, the leading platform for pickleball players to connect and organize games, is excited to announce the closing of a $2.5 million seed round.

This investment furthers their mission to enhance the on-court experience for players through technology, ensuring that every game is competitive, social, and fun.

Powering America’s Fastest Growing Sport

Pickleball is the fastest-growing sport for three consecutive years, now with over 36.5 million players in the U.S.—more than golf, tennis, and basketball.

All of that growth has created problems for players – court shortages, long wait times, and overwhelmed organizers.

Pickleheads solves these challenges and has quickly become the go-to platform for pickleball players nationwide.

• Nearly 9 million players visited Pickleheads to find courts, connect with others, and organize games.
• Ranked #1 Pickleball App on iOS and Android, with over 3,600 ratings and a 4.9-star average.
• 354,000 registered users, growing 405% year-over-year.
• Official court and game finder for USA Pickleball and the Global Pickleball Federation.

“Pickleball offers something we all need now more than ever — the joy of real-world connection,” said Max Ade, CEO and co-founder of Pickleheads. “It’s highly social, accessible to all ages, and a natural community-builder. That’s why we believe pickleball is destined to become the largest sport in the world.”

The Future of Pickleball – and Pickleheads

Pickleheads believes that every game should be a good game—fun, social, and competitive. While open play was once the gold standard, today’s players span a wide range of skill levels, making structured programming essential.

The company is now powering level-based formats of play that preserve the magic of open play while ensuring balanced, competitive games. Whether at a public park, YMCA, country club, or private facility, Pickleheads guarantees you’ll always find great games at your skill level.

“Many players know Pickleheads as the go-to court finder, but we’re quickly evolving into a complete platform to power rec play,” said Brandon Mackie, COO & co-founder of Pickleheads. “Organizers can set up games, collect payments, run round robins and recruit from our network of local players.”

The Financing

This $2.5M seed round was led by Overline, an Atlanta-based VC, with participation from Ardent, Oregon Sports Angels, Profluence Capital, Service Provider Capital, and Network Ventures. Additionally, Pickleheads welcomed over 65 new angel investors—many of whom are passionate players and advocates of the brand.

“Pickleheads is revolutionizing the on-court experience for players, and we couldn’t be more excited to support their vision,” said Sean O’Brien, Managing Partner at Overline. “We believe Pickleheads will become the go-to platform for pickleball players everywhere.”

Join the Pickleheads Team!

Pickleheads is growing and hiring a number of remote roles, including:

• Head of Engineering
• Product Manager
• Sales Representative
• Full-Stack Engineer
• Head of Content
• Event Marketing Manager

View all of the open roles at pickleheads.com/jobs