Matt here with your weekly Subscription Prescription 💊

This week’s dose is a hard-hitting call out for those areas you should be worrying about to keep subscribers: cancellation flows, onboarding emails, and loyalty redemption.

This week’s dose is an interview with Lydia Farmer, head of retention at DIME Beauty. She drops some absolute gems, it is worth a listen on your favorite platform:

Join Us Tomorrow: Great Subscription Experiences

This is an incredible panel! Subscription experiences from different industries coming together to talk about how the right experience drives both growth and retention.

Plus - it’s on my birthday! No need for a cake or present, just attend. ;)

This will be a great opportunity to share how brands are using experience as a differentiator.

💊 Why Your Subscription Strategy Falls Apart After Signup

We all want our subscriptions to be invisible—in the best way. Set it, forget it, and drive retention like clockwork. But behind the scenes, what makes a subscription actually work isn’t as glamorous as a flashy “subscribe and save” button.

In this week’s dose, I’m breaking down three critical—but often overlooked—subscription truths I’ve seen across brands doing retention right. Whether you're scaling a high-growth brand or trying to fix a leaky bucket, these are foundational.

Let’s dig in.

1. Your cancellation flow is where retention is won—or lost

There’s no sugarcoating this: If your cancellation flow is weak, you're leaving money on the table. Way too many brands are treating this like a throwaway moment, when in reality, it's one of the most powerful touchpoints in your entire subscription lifecycle.

Most churn comes down to a handful of reasons—too much product, not enough usage, not seeing value. But here’s the thing: if you know the reason, you can fix the problem. We've seen huge wins by offering options tailored to those exact concerns—offering schedule changes, showing people how to use the product better, and even integrating win-back offers right into the cancel process.

Discounts can help (and yes, they often work), but it's just as much about clarity, control, and customer trust.

2. Education is the best churn prevention strategy you’re not prioritizing

You can’t build a retention engine if your subscribers don’t know how—or when—to use your product. And this is one of the most common causes of churn I see, especially with products like skincare, supplements, or anything where results build over time.

If someone doesn’t know how long a bottle is supposed to last, or how often they should use it, they’re probably going to unsubscribe when they feel like they have too much. That’s not a product problem. That’s an onboarding failure.

What actually works is weaving education into your emails, SMS, and even your product pages: “This bottle lasts 30 days when used AM and PM.” This stuff is easy to overlook, but it's often the difference between someone staying subscribed or bouncing after month one.

3. Loyalty only works when it’s visible

Loyalty points don’t retain customers if they don’t know they exist. I’ve seen brands put tons of effort into loyalty programs, only to find that subscribers have no idea they’re earning points—let alone how to use them.

Here’s the fix: make loyalty part of the experience. Add it to your billing reminders. Show it inside the customer portal. Let people redeem points with one click during the subscription flow. When we implemented this with a client, we saw a major lift in engagement and retention, just from one simple addition to their reminder SMS.

Your best subscribers are also your most loyal. So make it easy—and rewarding—for them to stick around.

Bonus: Give your retention team the breathing room to think bigger

One last thing I have to say—and this one's for the founders and heads of marketing reading: your retention lead can’t be your strategist if they’re also your full-time campaign builder, portal manager, and part-time data analyst.

If you want big ideas—things like cohort-led winback campaigns, dynamic cancellation flows, loyalty-led onboarding—you have to give your retention team the bandwidth to think creatively. Great retention isn't just about plugging in flows. It’s about designing an experience. And that takes space.

So if you’re wondering why your subscription strategy feels flat, take a look at your team’s calendar first.

Until next Tuesday, that’s your Subscription Prescription. 💊

 - Matt Holman 🩺

The Subscription Doc