Ops, Honesty, and the Truth About Keeping Subscribers with Hattie Gilpin of Wellbel
Some people talk about retention. Hattie Gilpin actually lives it. This week on Above the Fold, I sat down with Hattie, director of operations at Wellbel and co-founder of HAM. Someone who understands the messy, unglamorous, insanely important operational layer every subscription brand depends on but rarely talks about out loud. If you care about churn, subscriber health, or the real levers behind a strong subscription business, this episode is one you’re going to want to sit with.
What I loved about this conversation is how honest Hattie is about the reality of running a high-growth subscription brand in a saturated category. We got into the core metrics operators actually use, the decisions that buy time for product efficacy, and the parts of retention brands love to ignore until their churn rate smacks them in the face. It’s one of the most tactical, insightful conversations I’ve had about the operator side of growth.
The Retention Metric Operators Really Care About
Hattie doesn’t waste time. When I asked her what she looks at first, she immediately said time to churn. Not because it’s trendy, but because it tells the truth. Time to churn reveals the exact moment customers bounce, which means it reveals what went wrong: education, expectation, product, timing, or operations. And that’s where things get interesting. She uses it as a map. Once you understand when people leave, you can finally understand why.
This is something so many brands skip. They guess, they assume, they build retention strategies off vibes. Hattie breaks down exactly why those early cohorts tell the whole story and how you can dissect them without drowning in a hundred spreadsheets.
The Case for Quarterly Subscriptions
We talked a lot about billing cycles and how switching from monthly to quarterly can actually transform your retention. Most brands don’t realize how much friction they're creating with monthly renewals, more emails, more charges, more reminders, more opportunities for someone to say “I’m over it.”
For a product like Wellbel, where results take around three months, quarterly isn’t just operationally smarter. It’s psychologically smarter. You slow down the reminders, reduce the touchpoints, increase the chance customers will actually see results, and suddenly retention starts looking healthier without a single discount added.
The Operational Failures No One Wants to Admit
I loved this part. Hattie gets real about the operational side of churn, the stuff marketers never talk about because it’s not sexy. Slow shipping. Bad SLAs. Fulfillment mistakes. Failed payments. Confusing customer portals. Poor communication. These things break trust quickly, especially in a subscription model, and they’re major drivers of churn even when the product itself is solid.
Hattie spends an enormous amount of time inside cancellation reasons, warehouse relationships, and process breakdowns because that’s where the truth lives. And honestly, she’s right. Sometimes churn isn’t emotional or complicated. Sometimes people cancel because their order was late. It’s that simple.
Buying Time for Customers to See Results
Wellbel is a great example of a category where education matters. People need time to see progress, which means ops and CX have to work together to create an experience that earns patience. Hattie walked me through everything from packaging updates to educational inserts to segmentation inside email and SMS, and why every single touchpoint needs a purpose. Not noise. Not filler. Actual value that reinforces consistency.
It made me think a lot about how many brands try to “fix retention” with copy or discounts when the real solve is experience. The way something arrives. The timing. The clarity. The care.
The Hard Truth: You Have to Talk to Your Customers
Hattie and I are deeply aligned on this. If you don’t have data, talk to people. Literally call them. DM them. Ask real questions. So many founders skip this because they think “real” data lives in dashboards, but nothing gives you directional clarity faster than a conversation. If you want to know why someone didn’t subscribe, call them. If your buy box is confusing, ask them. This is basic, and yet almost no one does it.
It’s probably the most undervalued retention strategy in the game.
Why Billing Reminders Matter Way More Than You Think
One of my favorite moments was when Hattie went off (in the best way) about billing reminders. Most brands treat them as a “heads up,” but she sees them as a huge lever. The language, the timing, the format, all of it impacts churn. The difference between “your card will be charged” and “your next shipment is on its way, stay consistent” is massive.
She’s actively A/B testing these flows and watching churn shift immediately. It’s wild how many brands overlook this.
The Story Behind HAM
We also dove into HAM, the analytics platform she co-founded out of pure operator frustration. If you’ve ever tried to manually piece together subscription data from Shopify, Recharge, Skio, Stay, whatever, you know the pain. HAM is built specifically for subscriptions. No ecommerce fluff. No irrelevant dashboards. Just real clarity for operators who need to understand billing cycles, retention by cohort, revenue per customer, and all the details that drive decisions.
It’s scrappy, smart, opinionated, and exactly what subscription brands need.
The Reality of 3PLs and Partnership
Another thing Hattie said that stuck with me: she chooses fulfillment partners based on communication and accountability. Not price. Not perfect software. She needs partners who think like operators, who tell her the truth, and who solve problems instead of sliding them across the table. Because fulfillment errors happen. SLAs slip. That’s life. The way a partner responds is what matters.
Again, simple, but not common.
The Unboxing Details That Actually Matter
We got into packaging and unboxing too, and this part made me laugh because she’s right, the best unboxing experiences are the ones that don’t overcomplicate things for the warehouse. Beautiful, branded, but simple enough that mistakes don’t happen. It’s about streamlining without losing the magic. And honestly? Most brands get this wrong.
Her Advice as an Investor
Hattie invests very early, and she shared what she actually looks for: not fancy metrics, but people with grit. Realistic plans. Clear thinking. The ability to get things done without chaos swallowing the whole company. Early-stage investing is about the operator behind the idea, not the deck.
I co-sign that deeply.
The One Action Every Subscription Brand Should Take Today
At the end, I asked her for one single piece of advice she’d give an operator trying to cut churn. She didn’t hesitate.
Test your billing reminders.
It’s simple. It’s immediate. It’s actionable. And it works.
If you’re building a subscription business, trying to strengthen your retention, or curious how real operators think beneath the surface, Hattie brings so much clarity and lived experience to this conversation. It’s tactical, smart, honest, and exactly the kind of perspective that makes you rethink how your brand actually runs behind the scenes.
