Here's how to get your whole pickleball setup on autopilot. This is where most organizers end up, and it works the same whether you're running round robins, open play, weekly drop-ins, or anything else.
Let me paint a picture for you:
- Your sessions are on an automatic weekly cadence.
- Your group gets auto-invited the moment a new session goes up.
- Your waitlist does the backfill work for you when someone bails.
- Payments are collected at RSVP, so no more chasing $15 on Monday morning (optional).
- You communicate easily with two built-in chats: one for the whole group, one for the players who RSVP'd that day.
Less time planning and more time playing. A few quick steps will get you there – let's dive in.
The setup
1. Create your group and add your players
Start with your group. This is what makes every future session auto-invite your players. Set it up once, and you won't have to build an invite list from scratch again.
In the app, create a new group and give it a name. Set it to public (anyone can join) or private (you approve who joins). Then get your players in using whichever option fits:
- Invite link. Paste it into your existing text thread or email list with your own context.
- QR code. Print it or show it at the courts for players to scan.
- Bulk invite (paste a list of emails or phone numbers all at once).
- Search and invite. Find players by name or skill level and send direct invites.
💡 Good to know: bulk invite is desktop-only. If you've got a list of contacts to import, do it from your laptop.
Once your players are in, come back here to set up your session.
For the full walkthrough on groups, check out our groups video series.
2. Set up your weekly recurring session
With your group in place, it's time to set up the session that runs on repeat. Set the schedule once and each week's occurrence generates itself automatically.
💡 Good to know: weekly recurring sessions are a Pickleheads Pro feature. If you're not on Pro yet, here's what's included.
Create a new session and choose Weekly game. Configure:
- Start date and an optional end date (leave the end blank if the series runs ongoing).
- Days of the week, start time, and number of courts.
- Player limit: this activates your automatic waitlist, so extra signups land in line and get promoted the moment a spot opens (learn how the waitlist works).
- When future invites go out (up to 7 days before each occurrence).
- Whether you auto-add yourself to each session (toggle off if you don't always play).
Hit Create session to create the series. You'll land on the invites screen next.
3. Turn on auto-invites for your group
On the invites screen, tap Invite groups and select your group from the list. A toggle for Invite every week will pop up – keep it on and hit Save.
Every weekly occurrence will now auto-invite your whole group. No manual work from you. Your weekly series is live.
4. Familiarize yourself with your new setup
Your session is live and your players are getting invited automatically. Before you close the app, take a quick look around your group so you know what's at your disposal.
Group chat. Lives on your group page and includes everyone in the group. Use it for broad announcements: "Next month's league is up," "Courts resurfaced, looking great," "Anyone want to sub in Saturday?"
Session chat. Lives on each individual session and includes only the players RSVP'd for that day. Use it for day-of logistics: "Running five minutes late," "Courts are wet, meeting at the covered ones," "Anyone find my water bottle?"
Group settings. Tap Edit on your group page and you'll find controls for adding co-admins, adjusting privacy, setting home courts, and managing who can message the whole group or invite new players.
The session page. For each week's session, you'll see the confirmed player list, the waitlist, and the session chat all in one place.
If you've been running your community in WhatsApp or iMessage, these chats don't have to replace that. Most organizers keep their existing thread for social chatter and move logistics, payments, and "who's in?" here, where that kind of traffic tends to pile up.
💡 Pro tip: you can lock group chat so only admins can post, which keeps announcements clean. Regular members can still react.
Want to Collect Payments?
If you're charging for your sessions (or want to start), you can turn on payments from the session settings. When a player RSVPs, their card gets charged at that moment and the money lands in your bank account. No more tracking who owes you, no more awkward payment reminders, no more no-shows who never paid.
First time turning on payments? You'll connect your bank through Stripe as a one-time setup. After that, every paid session auto-collects, including waitlist promotions.
💡 Good to know: you keep 100% of the price you set. Players pay a 7% service fee (capped at $10) plus Stripe's processing fee (around 2.9% + $0.30) on top of your price, so factor that into what you advertise.
For the full walkthrough, see collecting session payments.
Ready to Get Started?
Here's the action order once you're in the app:
- Create your group and get your players in.
- Set up your weekly session and attach your group in the invite settings.
- Connect Stripe and turn on payments for the session.
- Set your player cap so the waitlist can do its thing.
Not on Pro yet? Weekly recurring sessions unlock with Pro. Find out what's included in Pickleheads Pro.
Let it run for a few weeks. That's when the 10 minutes you just spent really start to pay back. You're good to go.
