Running a membership sounds fun, right? Build community, share your expertise, make recurring revenue. 🎉

But actually managing your membership? That’s the part no one talks about.

Because once you’re in it, you realize it’s less “laptop lifestyle” and more “chasing failed payments at 9pm while eating cold pizza” (I get it, cold pizza slaps).

And honestly, that’s why people start to regret their memberships. It’s not because the content is bad, or because your community isn’t engaged. 

It’s because of those little backend cracks in your systems that let energy, retention, and revenue slip away.

Let’s talk about the four sneaky troublemakers I see in almost every membership.

 

Top 4 Membership Management Problems

I’ve been managing membership systems since 2018, and let me tell ya, I’ve seen some things. 🙃

The kind of things that make memberships feel way heavier than they need to.

And nine times out of ten, it comes down to at least one of these four culprits: onboarding, payments, customer service, and offboarding. 

And where do most memberships spring their first leak? Right at the start – onboarding.

 

Leak #1: Onboarding That Sucks the Excitement Right Out

When someone decides to join your membership, they’re ready to dive in right now. They’ve already made the leap, the excitement is high … and then what happens?

They wait. Hours, maybe even days. Guess what sets in?

Buyer’s remorse and lost momentum.

I once waited a full week (!!) for access to multiple “instant access” purchases, sent multiple emails, and was this close 🤏🏻 to filing a dispute because I hadn’t heard back. Actually, this story fits in with TWO of these leaks … onboarding + customer service, but I digress.

And let’s not forget about the other side of onboarding that tends to lose people.

Even when access is instant, if they log in and feel completely lost, you get the same result. Excitement fizzles and once it’s gone, it’s tough to bring it back.

You might notice onboarding leaks if:

• You get “I don’t have access” emails shortly after someone joins
• People post in the community or email you saying “I’m sooo confused”
• New members don’t engage much in the community
• They cancel before they even really begin

A few simple ways to spice up your onboarding

• Automate the access (most platforms do this) AND routinely check in to make sure it’s working (especially if you’ve received emails about it).
• Add a Start Here checklist/guide or a short welcome video (or both!) I personally love a good brief walkthrough video when I get started.
• Even an automated “Day 1–3–7” email series starts new members off without confusion.

Deanna Seymour has an amaaaazing onboarding experience in her Playhouse community — I was hella impressed when I joined.

When onboarding is done right, it doesn’t just welcome people in. It gives them the confidence to keep showing up. And that one shift can turn a “meh, maybe I’ll cancel” member into someone who sticks around for the long haul.

 

Leak #2: Payment Tracking That Turns Into Mystery Money Problems

Expired cards, banks blocking charges, billing errors … it’s death by a thousand cuts. The worst part is, you might not even notice it’s happening until you’re missing hundreds of dollars.

That happened to a client of mine. She had numerous members accessing the content without paying, and we had to backtrack to try and recover her money.

Not only is that a total PITA, but it sours the member experience when it appears you don’t have your ish together.

You might have a payment leak if:

• You only hear about failed payments when a member emails you like, “uhhh why was I kicked out?”
• Revenue feels unpredictable, even when sign-ups look steady.
• You’ve been blindsided by mystery churn that you couldn’t trace back to anything obvious.
• You log into Stripe and notice failed payments, but you had no idea that was happening.

And then comes the awkward part: trying to chase people down after the fact. (Because nothing screams “fun” like sending “Hey, can you update your card?” emails on repeat 🙃).

Two simple payment systems I set up for clients:

• Automate the recovery process. Set up email reminders for members to update their payment before they get locked out. And for the love of cheese curds, include the direct link to update their payment (can’t tell you how many times I’ve had to dig).
• A simple Airtable tracker helps you keep track of failed payments so you can stay proactive in managing them instead of scrambling after the fact. It doesn’t have to be Airtable – you can set a similar system up on most platforms like Clickup, Asana, even Trello or Google Sheets.

When payment tracking is in place, you’ve got a quiet little safety net running in the background. Revenue feels steady, members stay supported, and you get to skip the cringe-worthy money convos altogether.

 

Leak #3: Customer Service That Gives You The Monday Morning Scaries

Picture this: it’s Monday morning. You grab your coffee, sit down at your desk, and brace yourself for whatever fresh hell is lurking in your inbox. Not exactly the energizing start you had in mind.

Between answering the same five questions over and over, dealing with complaints, and (the real fun) processing refunds or disputes … it’s enough to make anyone over it.

When members don’t know where to find answers, their first move is to email you. Or DM you. Or both. And while being helpful feels good in theory, the constant interruptions pull you away from the fun parts of your business.

You might have a customer service gap if: 

• Your inbox is overflowing with the same questions over & over, just worded differently.
• Members complain about slow support (don’t they know you’re just one person doing it all?!) 
• You feel like you’re running tech support instead of a membership.
• You simply can’t keep up with the number of emails coming in every day so you put them off, and get follow-up emails from frustrated members.

My story above? The customer service was seriously lacking. There wasn’t any communication until a week later when they let me know that I would have access now.

I truly get it – customer service can be really hard to keep up with. You didn’t start your membership to be glued to your inbox, fielding the same questions & issues day after day. Yet, here we are.

You’ll never truly get away from CS issues because that’s show business for ya … but you CAN make it a bit easier on you and your team.

How to set up customer service systems that support you:

• Start with a simple FAQ page that’s included in your Start Here guide – so members can help themselves when something comes up. You can even include it in your autoresponder in case they can answer their own question.
• Create saved replies/templates for common questions so you’re not typing the same thing from scratch a hundred times.
• If you’re feeling fancy, you can set up a ticketing system (Airtable, Google Forms, whatever works). It keeps everything in one place AND shows you which questions pop up the most so you can update your resources.

When you’ve got systems backing you up, members get their answers faster — and you get your time and sanity back. Cue the angels singing.

 

Leak #4: Offboarding That Slams the Door Shut

Cancellations happen. They’re part of running a membership. But how you handle that moment can decide whether a member leaves for good … or circles back later (maybe even bringing a friend with them 👀).

If your offboarding process is just a cold cancellation notice or an automated “your access has been revoked” email, that’s a pretty gnarly leak. 

You’re not just losing their payment — you’re losing feedback, goodwill, and the chance for a future re-join.

Offboarding leaks might show up like: 

• Cancellations that feel like a slammed door with no goodbye wave.
• Rarely hearing why people are leaving — they just ghost, and you have no idea what happened.
• Past members never return, even though they seemed to like your membership when they first joined.

Having a cold (or nonexistent) offboarding means missed insights, missed re-joins, and missed opportunities to end on a positive note.

How you can set up intentional offboarding:

• Add a one-question exit survey: “What made you decide to leave?” Sure, not everyone will answer, but the ones who do can give you some useful little nuggets.
• Send a simple thank-you email that leaves the door open: “We’d love to have you back anytime.”
• Bonus: create a “come back” offer for returning members who decide to give it another shot.

When you handle cancellations with intention, they stop being the end of the story. Offboarding becomes just another step in the member journey — one that protects your reputation, gives you valuable insight, and makes it easy for people to return when they’re ready.

 

Because Membership Mayhem Isn’t a Growth Strategy

There is no such thing as a bad time to set up membership systems. Sure, it’ll take less time if your membership is small but sometimes, you just don’t know what you don’t know. And that’s okay.

You’re thinking about those systems now and that’s why I wrote this so I would say that’s a big ol’ win! But if you’re still feeling a bit overloaded with the whole idea of setting up your systems (even if you start small) …

… that’s exactly what I do inside my Membership Systems Audit & Cleanup. I’ll walk through your full member journey, find the cracks, and clean up the messy backend pieces so everything flows.

Because when your systems work, your membership works. It feels lighter, easier, and way more sustainable.

Ready to finally fix the leaks? Book your Membership Systems Audit & Cleanup