How to earn more money using Pickleheads payments

As rec pickleball gets more serious, there’s a real hunger for well‑run events — and people will pay for them.

This guide shows how to ride that demand with formats people happily buy, and how to run them end‑to‑end in Pickleheads so you keep the experience smooth and the admin light.

If you’re reading this, you’ve probably either received your first payment or you’re ready to flip the switch. This guide is the playbook I’d hand to any organizer who wants to turn that interest into dependable revenue using Pickleheads, without becoming a full‑time administrator.

Along the way, I’ll point to what’s working for high‑volume programs and share what we’ve learned from Pickleheads organizers who have scaled their business.

If you haven’t used the Pickleheads payment feature, here’s how it works. It starts by connecting a Stripe account to your Pickleheads account. Once that’s set up, it’s as simple as toggling on a switch on your next pickleball session.

You set the price and details on your event. Players pay right on the Pickleheads event page — we accept card, Apple Pay, or Google Pay — and you see payouts land in your bank each week.

Rosters, receipts, reminders, and check‑in all live in the same place, so you’re not juggling forms and group chats. Turn on waitlists, and you can backfill no‑shows automatically.

Organizers pay $0 in fees to use Pickleheads payments. Every extra spot you sell actually lands in your pocket.

Serious pickleball players pay for one primary thing: match quality. Formats that sort by skill and keep rounds on time win repeat players.

No matter the style of play, your description should make it obvious who it’s for (3.0–3.5, 3.5–4.0, 4.0+), how long it runs, and what “good” looks like. That’s how you build trust—and a habit.

Bonus points if you can start to build community, too. Till Schmidt, who scaled from one court with four friends to three Sunday sessions and nearly 100 players, said it best: “The biggest growth driver was a group photo every week—tag everyone, post to Instagram, and link the next session.”

Below are the workhorse formats for any paid pickleball session on Pickleheads. I’ll share where each shines, what people typically pay, how to handle skill levels, and how to run it on Pickleheads.

Pricing varies by market, but you can use these as starting points and adjust once you hit steady sellouts.

If your crowd skews mixed‑level or social‑first, start here. Run 90–120 minutes with rotating partners and short water breaks. Keep the cap tight to avoid long waits.

Typical pricing lands between $10–$20 per player, though big‑city evenings can stretch to $25+. If you want a little extra sizzle, set aside $5 optional prize money for a fun MVP or winners’ pot.

Skill levels: List “All levels welcome” but mention simple level cues at check‑in—wristbands or tags so players self‑sort without awkwardness.

Run it on Pickleheads: Create a Popcorn round robin, set 10-12 minute rounds, and let the Round Robin Tool handle rotations and court assignments.

Skill-based round robins promise variety and fairness without tournament overhead. Organize by level (3.0–3.5, 3.5–4.0, 4.0+), run to 11 or on a timer, and take a quick podium photo at the end. That gives everyone shareable proof that the night had a finish line.

The typical two‑hour entry fee is $15–$25 per player. If you want to bump demand, earmark 10–15% of entries as prize money for the top finishers.

Skill levels: Enforce gently but clearly. If someone signs up out of range, move them before the night of the event so trust stays high.

Run it on Pickleheads: Set up a Gauntlet on the round robin tool, or try one of our other formats. The app generates matchups by seed and results each round and tracks live standings. Aim for 4–6 rounds.

Ladders are the best answer to “I just want fair matches.” Start with a seeded order (self‑reported, organizer ranked, or results from last week), then promote and relegate based on wins.

Players love the upward path, and you get predictable weekly revenue. Drop‑ins typically run $10–$20 per night; seasons (6–8 weeks) often price $60–$175 per player depending on venue costs.

Skill levels: Set divisions (e.g., 3.0–3.5, 3.5–4.0). Movement rules should be public so players trust the system.

Run it on Pickleheads: Use the Round Robin Tool and choose a format with a seeded set-up. You can arrange the week one seeding, then let results move players up or down courts based on performance.

Ratings are no longer just for tournament players. A dedicated DUPR night gives people a clear payoff: competitive games plus verified scores that count. Two hours, tight pacing, and clear instructions on how results are recorded are the keys.

Typical pricing is $15–$25 per player; you can charge more if you’re offering formal evaluations.

Skill levels: Gate by band (e.g., 3.5–4.0), but welcome unrated players. Their first results will create a rating.

Run it on Pickleheads: Record scores each round and submit verified results to DUPR from your event dashboard. I recommend using the Up & Down the River format. It’s the gold standard for DUPR because it’s the most fair. Players are grouped by level, and they play with every person on their court before moving up or down.

Consider a small prize purse for top aggregate wins to nudge sign‑ups.

When players want to pair off in teams and compete for glory, this is the format to use. Run pool play into a bracket final that will yield a champion.

The typical entry is $20–$35 per player; if you advertise prize money, set aside 10–20% of entries for the purse.

Skill levels: Make sure you have balanced pools with players that have about the same average rating. You don’t want to have a 4.0 pool and 3.5 pool that both feed to the bracket – turn that into two separate tournaments.

Run it on Pickleheads: Our mini-tournament format is perfectly set up for this.

Start near your true costs if you’re building trust. Once a session sells out three weeks in a row, nudge the price $1–$2.

Prime evenings can carry a small premium; mornings a small discount. Early‑bird tiers reward the players who book first and help you forecast demand.

If you’re offering prize money, be explicit about the split and keep it simple. Protect margins with a clear 24‑hour cancellation policy and let the waitlist backfill no‑shows automatically. Long waitlists are your signal to raise prices or add a second wave on the same courts.

Pick one anchor slot and make it a habit. Publish it weekly and keep the copy consistent so players recognize it.

When you’re reliably full, add a second wave (same night, later start) or test a weekday morning for your die‑hards. Recruit a trusted regular to handle check‑in and start the first round so you can host, greet, and keep courts moving.

That’s how Till scaled Sundays to three sessions across 6–8 courts each without losing the social feel that made people stay.

The players are ready. They’re taking the sport seriously and they’ll pay for formats that deliver fair, fun, on‑time play. Your job is to set a clear promise, enforce skill levels kindly, and let Pickleheads handle the heavy lifting—payments, reminders, rosters, matchups, standings, and DUPR submissions.

Pick one format. Pick one time. Publish it with payments on. Take the photo at the end and link next week. Do that three weeks in a row and you’ll feel the momentum kick in.