I didn’t figure out membership retention overnight. My first program?
Had solid content, a decent number of sign-ups… and a massive drop-off after 60 days. People left faster than I could say “monthly value.”
At first, I blamed everything but myself: the platform, the price, the timing. But then I realized… I wasn’t actually talking to my members after they joined. I was emailing them when I wanted them to buy, not when they needed support, reminders, or encouragement.
Email marketing changed all that. It became the glue that held everything together. These 8 best practices helped me stop the churn and build a community that actually sticks. Here’s how I do it.
1. Send a Strategic Welcome Sequence
First impressions matter more than most people realize. When someone joins, don’t just hit them with a receipt.
I send a 3-part welcome sequence:
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Email 1: Welcome + What to Do First
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Email 2: Benefits breakdown + how to access them
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Email 3: Quick win or member success story
People are way more likely to stay when they feel like they’re already winning after signing up. Here’s a good guide on writing engaging welcome emails for customers that helped me craft mine.
2. Set Expectations Early and Often
Ever subscribed to something and had no idea what was supposed to happen next? That’s a recipe for cancellation.
In my early days, I didn’t tell people when to expect content. Now I spell it out:
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“New lessons every Monday”
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“Live call the first Thursday of the month”
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“You’ll get a recap email each Friday”
You reduce overwhelm and build trust when people know what’s coming.
3. Use Behavior-Based Triggers
This was a game-changer for me.
If someone hasn’t clicked a link in 30 days? They get a “Need help getting started?” email.
If they complete a course module? I send a “Great job — here’s what’s next” message.
These automated nudges help keep people engaged without me lifting a finger. Tools like ConvertKit, MailerLite, or ActiveCampaign make this super easy — especially when paired with a strong automated email sales funnel.
4. Share Recaps and Roundups
People are busy. Even your most loyal members miss stuff.
That’s why I send a monthly email with:
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Top 3 pieces of content they may have missed
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Upcoming events
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Popular questions from the community
It reminds them of the value they’re paying for and it works. Engagement always jumps after these go out. You can learn how I structure these from my monthly newsletter creation guide.
5. Celebrate Milestones and Anniversaries
I’ll never forget when a member emailed me back and said, “Wow, no one’s ever congratulated me for sticking with something before.”
Now I automate milestone emails:
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“You’ve been with us 3 months — look how far you’ve come!”
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“1-year member — you legend!”
These tiny touches create big emotional wins. If you want to take it up a notch, consider using storytelling in email marketing to make these moments even more memorable.
6. Collect and Respond to Feedback
You can’t fix what you don’t know is broken.
Every 60 days, I send a short feedback email. Sometimes it’s a survey. Sometimes it’s just a single question: “What would make this more valuable for you?”
Even if only 20% reply, those insights have helped me improve retention more than any course I ever took.
7. Personalize Everything You Can
Look, no one wants to feel like “Dear subscriber.”
I use:
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First names
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Membership join dates
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Tags based on activity (like what content they’ve accessed)
It’s not creepy — it’s just thoughtful. And it massively increases open rates and replies. If you’re unsure where to start, try segmenting your email list for better targeting.
8. Always Offer a Reason to Stay
Every email should remind members why they joined. Whether it’s:
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A new resource
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A bonus
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A sneak peek
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A success story
Give them something that says, “Hey, staying in this membership is a smart choice.”
I include at least one “don’t-miss-this” link in every member email. And yep — I track which ones get clicked.
Final Thoughts
Email isn’t just a marketing channel. It’s a retention engine.
When you use it with intention — to welcome, encourage, re-engage, and celebrate — you build relationships that last longer than any funnel ever could.
You don’t need to do it perfectly. Just start doing it consistently.
Because keeping your members? That’s where the real growth begins.
