Matt here with your weekly Subscription Prescription 💊

Great products need better subscription experiences. This is what great brands do consistently - onboard, communicate, and get customers using their product.

This week’s dose is also an interview with Thomas Lalas, the founder of the Art of Ecom. Tons of retention experience and worth a watch or listen:

💊 What Great Subscription Brands Get Right

The deeper I go into subscription retention, the clearer it becomes: most brands don't fail because their product is bad. They fail because they never gave the customer a reason to believe in it in the first place.

What separates brands that retain well from those that constantly churn and burn. It’s not the price. It’s not the packaging. It’s how well they guide the customer after the first purchase.

Here are three things I’ve seen move the needle most:

1. First-week engagement isn’t optional — it’s an extension of the product.
The moment someone buys, they enter what I call a “skepticism window.” They’re unsure if they made the right call. They’re watching their inbox and wondering what happens next. Most brands go quiet here. But this is exactly when you should be reinforcing trust.

If your product takes time to work, this is where you explain why. If your product delivers fast results, this is where you highlight what to look for. Video walkthroughs, founder notes, milestone tracking - anything that reduces doubt helps you keep that customer.

One brand I’ve seen execute this well is Everyday Dose. They use a founder-led video immediately after purchase to explain how the product works, what effects to expect in the first week, and how long it usually takes before the deeper benefits kick in. It’s not flashy, but it’s real, and it immediately reframes the first few days as a journey instead of a gamble.

2. The billing reminder is your most misunderstood retention tool.
Too many brands treat billing reminders like a legal obligation instead of a strategic touchpoint. If your email says “You’re about to be charged,” don’t be surprised when people cancel.

What works better is reframing. “Your next freebie is unlocking soon.” “Your journey is progressing.” “Your order is ready - here’s what’s inside.” You can still give customers options to delay or cancel, but when you pair that with upgrades, referrals, or education, you’re not just reminding them, you’re re-engaging them.

Obvi does a solid job with this. Instead of sending a plain transactional email before renewal, they frame it as a moment of progress. The messaging highlights what’s coming in the next box, includes an optional bonus product the customer can add with one click, and ties it back to the larger transformation the customer signed up for. It becomes something to look forward to, not avoid.

3. Product adoption drives everything — and cadence is king.
If someone doesn’t use the product consistently, they won’t stay subscribed. It’s that simple. So I’ve started building onboarding education around this core idea: teach cadence.

Quick wins help. Bite-sized video “masterclasses” work even better. Not only do they make customers feel like they’re learning something, but they also deliver a sense of progress before the product has had time to work. And yes, the data shows that customers who engage with this kind of content click more, stay longer, and make more purchases.

Bumpin Blends absolutely nails this. Their post-delivery education includes a short series of SMS messages and emails with quick smoothie tips, best practices for storing blends, and how to make the most of your subscription. They even ask for feedback early to spot customers who need support. The result? Better usage, better reviews, and longer retention.

Conclusion

Subscriptions don’t thrive on hope. They thrive on structure. You don’t need to manipulate or hide the cancel button. You need to educate, engage, and guide.

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

 - Matt Holman 🩺

The Subscription Doc