Membership retention strategies for creators: 6 systems that keep members for years
If you run a membership, you’ve probably experienced this at some point: people join excited, then quietly disappear. There’s rarely a precise moment where things “go wrong.” But when you see that Stripe cancellation notice, it’s hard not to wonder whether your membership is actually working.
When churn shows up, many community builders look first to their marketing. They think about more promotion, launches, and visibility. Those pieces matter. Sustainable growth, though, also depends on what happens after someone joins and whether the experience gives them a reason to stay.
Josh Hall’s Web Designer Pro is proof. With just 250–300 members and no community manager, his membership generates $327K in annual recurring revenue and more than $817K over five years. These results come from a set of membership retention strategies built into the community from day one.
In this article, we’ll break down the exact systems Josh shared at Circle’s Future of Communities Summit in 2025. You’ll learn
- how to help members get value quickly,
- build ongoing relationships inside the community, and
- use Circle’s features to turn a small, creator-led membership into something people stay in, renew, and return to over time.
Why retention matters more in small communities
In a small membership community, a handful of cancellations can immediately affect monthly revenue, making every renewal matter more. That’s why online community retention isn’t a “nice to have” at smaller sizes. It keeps the business stable.
“When you think about a membership that’s knocking on the door of a million dollars, you probably think you need thousands of members,” says Josh. “That’s not the case. Depending on the price points and the experience you want to craft, you can do it with a very reasonable number of members, especially if you focus on retention.”
Josh built Web Designer Pro to fit his life, with his family and personal freedom as top priorities. He didn’t want a large, scaled community. His goal was a balanced business that could support his life while still creating meaningful value for members.
In small communities, retention compounds over time:
- Long-term members drive referrals and word of mouth
- Deeper participation leads to more meaningful transformation
- Less pressure to constantly launch or promote
So, what did Josh do to turn his small membership into a sustainable, compounding growth engine?
1. Nail the first impression
Josh’s philosophy is simple: onboarding is retention.
The first few days introduce members to how the community works and help them understand next steps. It can also directly affect whether they come back and start using the community in a meaningful way. If the start feels confusing or impersonal, many members never fully engage.
How Web Designer Pro puts this into practice
The fastest way to show a new member they matter is to acknowledge them directly.
In the early days of Web Designer Pro, Josh welcomed every new member with a short personal video.
What that looked like in practice:
- A quick Loom video sent after someone joined
- A personal note like, “Hey, I’m Josh. I checked out your site. Here’s what I noticed.”
- A simple question asking about goals and challenges
Today, Josh uses Circle’s automations to scale this while keeping the human touch, following membership onboarding best practices:
- An automated DM with a warm welcome video
- A prompt to reply with goals and current priorities
- A personal follow-up message or Loom once they respond
Why this drives retention
A personal welcome grounds the experience in a genuine interaction from the start. Seeing and hearing from the community leader helps new members recognize a face and name.
“I have so many members who got a video from me five years ago and still talk about it today,” Josh says.
That first exchange provides members with a clear point of contact and makes the community feel like a place where people notice when you show up.
How to implement this in Circle
2. Set up success pathways
After the initial welcome, members are more likely to stay engaged when they can see a clear next step.
“People don’t want more information. They want a result,” says Josh.
That starts with understanding where someone is in their journey and giving them a path that makes sense for that stage.
How Web Designer Pro puts this into practice
Over time, Josh noticed that most members fall into one of three stages based on where they are in their business, each with different needs:
- Builders are new web designers who are just getting started. They need fundamentals and quick wins that help them land early clients and build confidence.
- Growers already run a business and earn roughly $20,000 to $50,000 annually. Their path centers on pricing, positioning, and systems to reach six figures.
- Scalers run established agencies at six- or multi-six-figure revenue. They come for higher-level strategy, leadership advice, and coaching that fits a growing team.
Why this drives retention
Distinct success pathways mean members don’t have to guess where to start or scroll through an endless library of content hoping something clicks. Members know where they fit and what to focus on next.
The different member types also support one another.
“Builders help Builders, Growers help Builders, and Scalers help Growers,” says Josh. “But Scalers also learn from Builders because they’re experimenting with new tools.”
This structure drives retention because:
- New members get early wins tied to their stage
- People know which courses, community events, or conversations matter most
- Members learn from peers who are slightly ahead or trying something new
- Scalers stay involved because the community continues to stretch them
This supportive membership tiering is also exactly how Pat Flynn grew SPI to $1M+.
How to implement in Circle
Once you define your core member stages, use Circle to connect them to key actions:
- Use profile fields so members select a stage that reflects where they are right now
- For each stage, recommend specific resources, events, and spaces
- Create a simple “First 30 Days” checklist for early guidance
💡Map out your member success pathways with this framework:
3. Turn members into friends, partners, and teammates
At a certain point, retention stops being about features or programming. It becomes (and continues to be) about the people.
As Josh puts it: “Is there any better way to retain a member than for them to find their people?” Friendships and collaborations provide compelling reasons to stay.
How Web Designer Pro puts this into practice
The strongest retention loops form when members begin relying on one another. That’s a big part of how Web Designer Pro answers the question of how to reduce churn in a membership.
Josh points to Sam, a long-time member, as an example. Sam shared that Web Designer Pro “paid off in so many ways,” from making close friends with other entrepreneurs to learning from people with different specialties to hiring another Pro member as part of his team.
Web Designer Pro enables this relationship-building through several intentional strategies, including:
- Wins and Successes space that highlights progress and builds trust
- Pros for Hire space where members find collaborators and contractors
- Dedicated spaces where members share their unique skills and experience
- Weekly member hangouts and coaching calls
- Member-led workshops that turn expertise into shared learning
These patterns turn the community into a place where actual work and relationships happen.
Why this drives retention
Inside Web Designer Pro, members can find collaborators, specialists, and even teammates. Over time, that shared context builds. Staying means keeping access to people who make their work easier and better.
How to implement in Circle
Circle gives you the structure to help members build authentic, deep connections over time:
- Create a Wins space where members post updates and comment on each other’s progress
- Use custom profile fields or pinned threads so members can list their skills and what they’re looking for
- Host weekly hangouts or coaching calls where members can see each other regularly
- Invite members to lead workshops to share their expertise or solutions they’ve built
4. Reinforce member identity and ownership
At some point, members stop treating the community like a tab they open and start treating it like a place they belong.
It shows up in small ways. They reference it in conversation. They add it to their bio. They keep the hoodie in rotation.
Over time, the community becomes part of how members talk about their work and present themselves. Once that happens, staying doesn’t require convincing. It just makes sense.
How Web Designer Pro puts this into practice
You can spot strong online community retention when members carry the community with them, beyond the platform. They wear it, reference it, and use it as part of their professional identity. In a small membership community, that sense of ownership carries weight.
Josh leaned into this with Web Designer Pro in simple, practical ways.
“With Web Designer Pro, the easiest way is swag,” he says. “It helps that the brand looks cool on a shirt and is really recognizable.”
In one case, a member landed a $5,000 website project just by wearing her Pro shirt to the vet.
💡Pro tip: This is why naming your community can be so crucial. Branded swag with “Pro Web Designer” makes you look elite, while “WDP” will mean nothing to most.
Here are a few more ways Josh encourages members to represent the community publicly and professionally:
- Shareable templates, like a five-year anniversary graphic, that members can post publicly
- Badges and logos that members can add to their websites to signal credibility
- An affiliate program that lets members earn recurring revenue by recommending Pro
Why this drives retention
Those moments build both pride and practical value. Members gain visibility, credibility, and, in some cases, income through affiliate referrals. Over time, that personal upside makes staying feel worthwhile and easy to justify.
How to implement in Circle
Members are more likely to use community assets when they know where to find them and how to apply them.
Some ways to build this out in Circle:
- Create a Member Assets space
- Add badges, templates, and a simple brand kit
- Include short website blurbs and swipe copy that members can reuse
- Pin a post that explains when and where to use each asset
- Trigger a workflow to send promotional assets whenever a member levels up—whether through engagement milestones or tier upgrades
5. Create IRL opportunities for connection
A coffee meetup, a shared table at a coworking space, or a single day together can change how members relate to each other afterward.
IRL moments add context that’s hard to recreate online. Meeting face-to-face often helps members engage more easily. The community feels more tangible because it’s tied to a shared experience, not just a screen.
How Web Designer Pro puts this into practice
Josh plans in-person touchpoints to align with the community’s size and needs.
- Member-led local meetups which usually consist of two to six people meeting at a coffee shop or coworking space. Josh calls these “micro retention” moments.
- A small annual conference with around forty members. “It was absolutely incredible,” Josh says. “I’m still buzzed from it months later.”
- Online follow-up after in-person events, such as a group call where attendees reconnect and continue the conversation.
- Event logistics hosted inside the community, including schedules, RSVPs, and a private group chat for attendees.
Each touchpoint reinforces the others, connecting members before, during, and after in-person meet-ups.
Why this drives retention
IRL experiences often lead to genuine friendships and a stronger sense that the community fits into their real lives. Photos shared afterward, event recaps, and follow-up calls help sustain that momentum.
Even months later, shared memories keep members connected and engaged online.
How to implement in Circle
Don’t let IRL plans get lost in DMs or email threads.
Use Circle to keep everything organized and easy to find:
- Use Events to host local meetups and post-event reunions
- Create a Meetups & IRL space where members share plans and photos
- Add city or region tags so members can find others nearby
- Keep RSVPs, updates, and follow-ups in one place
6. Keep the door open for “boomerang” members
Cancellations aren’t always a sign of dissatisfaction. Often, they reflect timing, budget, or a change in focus.
“When somebody leaves, it doesn’t mean they’re never going to come back,” Josh says.
Seeing churn as a lifecycle makes space for return. Members can step away when needed and rejoin at their convenience, without starting from zero.
How Web Designer Pro puts this into practice
Offboarding is one of the most overlooked membership retention strategies, especially in small communities.
When someone cancels Web Designer Pro, they receive an automated message that still feels personal.
Here’s what Josh includes in his offboarding flow:
- A personal thank-you for their time in the community
- A simple question asking why it wasn’t the right fit
- Reassurance that the community keeps improving
- An explicit invitation to return when the timing feels right
The message also makes one thing clear: leaving doesn’t close the relationship.
“I want them to know Pro is always getting better,” Josh says, and that their input still matters.
Why this drives retention
Treating the cancellation experience thoughtfully makes a difference. When someone signals they want to return to the community, Josh sometimes offers a reason to come back sooner, such as a limited-time annual discount.
Staying visible through email, social media posts, and his podcast also keeps the community top of mind, making rejoining feel like a natural next step rather than a hard sell.
How to implement in Circle
Make rejoining easy by treating former members as part of your ecosystem, not a closed chapter.
A few ways to set this up in Circle:
- Tag members as canceled when they leave
- Trigger an automated message that thanks them and invites feedback
- Add them to a winback segment for occasional updates
- Share rejoin offers, significant improvements, or upcoming events
Putting it all together: Your retention system checklist
Josh built Web Designer Pro around a small set of systems that support members at different stages in their journey and reinforce one another over time.
The 6-part retention stack
Each lever works on its own, but they’re strongest together.
- Personal first-touch welcome. Send a short DM asking what they’re working on right now and why they joined.
- Success pathways. Group members by stage, and assign each group one clear next step.
- Collaboration and connection spaces. Create a wins space or a place to ask for feedback on real work.
- Identity and ownership. Give members badges, templates, or merch they can use publicly.
- IRL moments. Encourage one small local meetup or host a single in-person event.
- Offboarding and rejoin messaging. Thank members when they leave and invite them back when timing changes.
💡What to implement in the next 30 days. Pick one small action from each category, like a welcome DM, a stage-based path, a wins space, and a simple offboarding message.
How Circle supports member retention
Circle helps turn these ideas into repeatable systems:
- Automations: trigger timely messages without manual work
- DMs: create personal first touches and follow-ups
- Spaces: anchor habits like sharing wins or asking for help
- Events: coordinate recurring touchpoints, online or IRL
- Member tagging and tiers: reinforce identity and guide access over time
Build a membership that people choose to stay in
Retention isn’t a single tactic. It’s the result of many small, intentional choices that shape how members experience your community over time.
As Josh puts it, when people are learning, getting wins, and building real relationships, “they’re going to come back.”
Want a platform built to keep members, not just collect them? Start a free Circle trial and set up your welcome DMs, success pathways, and retention spaces in one place.
