I used to think upselling inside a membership was kinda shady. Like, isn’t the whole point of joining a membership to get everything?
That was my mindset… until I launched my first membership program and left so much money on the table.
It wasn’t until a fellow creator casually asked, “What’s your upsell strategy inside the membership?” that I realized I had none. I was offering monthly content, resources, even office hours — but I wasn’t giving members the option to go deeper, faster, or bigger with me. And honestly? That was a disservice to them and to my business.
Since then, I’ve tested a bunch of different upsells inside my membership program — and the results have been wild. I’m talking higher retention, bigger revenue, and way more engaged members who are actually getting results. If you’re running a membership site or even thinking of starting one, let me walk you through five legit benefits of adding upsells inside your membership program.
1. Increased Monthly Revenue Without Needing New Members
This one hit me like a brick.
I kept thinking I needed more members to grow — but nope. I just needed to offer more to the people already inside.
After adding a “VIP Coaching Call” upsell ($97/month) to my $29/month membership, about 12% of members upgraded within 30 days. That’s pure extra income from people who were already paying me. No extra ad spend. No chasing new leads.
And it felt good, too — like, I was finally giving them a way to get more support instead of pretending one-size-fits-all content was enough for everyone.
If you’re still working on your structure, here’s a solid read on how to start a membership site in 9 simple steps to get your foundation right.
2. Better Member Retention (Because They’re More Engaged)
Here’s what surprised me most: people who upsell stay longer.
At first, I thought selling more might scare them off. But turns out, members who commit to a deeper level of support or content become way more connected to the community. They open emails. They show up to calls. They ask questions.
And yeah, they stick around.
One member told me, “Honestly, the upsell kept me from quitting. I finally got what I needed.” That moment made me realize upselling isn’t about pressure — it’s about providing options.
If you’re focused on loyalty, these membership retention strategies are a must-read to pair with your upsell system.
3. You Can Segment Members Based on Interest and Needs
Before upselling, I treated everyone the same. Same content. Same path. Same value.
But that doesn’t work long-term.
Some members just want templates and quick wins. Others want deep strategy and feedback. By offering upsells like a 1:1 audit, a private Slack group, or bonus trainings, I could segment my audience based on where they were at — without having to overhaul the core membership.
Now, I know who my high-intent buyers are. And I serve them so much better.
If you need content ideas for your offers, check out these best content types for membership sites that attract all kinds of learners.
4. Easier to Justify Higher Ticket Offers Later
This one’s huge.
Once someone’s bought a $49/month membership and then upsold into a $197 course, they’re way more likely to trust you with a $1,000 offer down the line. It’s like dating before marriage — they’ve already said “yes” in smaller ways, so a bigger commitment doesn’t feel scary.
I call it “micro-yes stacking.” Each upsell is a soft step forward, and if the experience is great? They’ll keep saying yes.
So if you’ve got big-ticket coaching or group programs, offering a premium add-on inside your membership makes the next step way smoother.
Need inspiration for how to roll this out? Here’s a great resource on creating a loyalty program for members that naturally feeds your upsell strategy.
5. More Flexibility Without Burning Out
This one saved me.
Running a membership can be exhausting if you try to give everything to everyone. But with upsells, you can shift the load. Instead of offering high-touch support to all members, you offer it to those who want and pay for it.
My time spent in support dropped 40% after offering a private Q&A tier. And I got paid more to support fewer people at a deeper level.
And if you’re selling through platforms like Payhip, here’s a guide on how to use Payhip for membership sales including managing upsells seamlessly.
Final Thoughts
Look, if you’re running a membership and haven’t added upsells yet… I get it. It feels weird at first. But I promise you — it doesn’t have to be sleazy or pushy.
It can be generous. Like saying, “Hey, if you want more, I got you.”
The key? Keep your core membership valuable on its own. But offer next-level support, content, or access for those who want it. Make it easy to say yes. And then watch your revenue and retention grow — without adding a single new member.
If you’re wondering how to structure your upsells or what to offer, hit me up. I’ve tested it all — and I’d love to share what’s worked (and what flopped, too).
