Dose #177: The 3 Subscription Mistakes You Should Fix Before BFCM

Matt here with your weekly Subscription Prescription 💊

I’m typically a pretty positive person, but some things just drive me nuts. No, I’m not talking about Utah drivers in this week’s dose. Instead, these are my three subscription pet peeves: treating subscriptions like a retention play, sending bland, lifeless billing reminder emails, and not using a founder video in the cancel flow.

This week’s dose is also a full podcast episode. Listen to my endless complaining this week on your favorite platform:

🎯 Fix These Three Mistakes TODAY

This week’s dose is personal. I’ve worked with hundreds of subscription brands at this point, and look at hundreds more, and there are a handful of things that I hate seeing.

If you’re doing any of these, don’t take offense. Just take action. Fixing even one of them can have a big impact on how your program performs heading into Q4.

1. Thinking subscriptions are a retention play

This one might be controversial, but I stand by it. Most brands treat subscriptions like they live entirely downstream. Someone buys once, then you try to convince them to stick around.

But the truth is, subscriptions are won or lost at acquisition. If your subscription team isn’t involved in conversion rate optimization, testing offers on PDPs, or designing the buy box, you’re making it harder to grow.

Some of the best lifts I’ve seen lately come from simple, smart offer strategies. A bulk subscription that gives the customer two months’ worth upfront. A gift with purchase that adds perceived value. A “starter bundle” with a built-in onboarding flow.

All of these help you acquire subscribers who are more committed, better educated, and more likely to stick around. Retention starts with who you’re bringing in and how you’re framing that initial purchase.

If you’re trying to grow your subscriber base, then get more involved in how you acquire them.

2. Sending lifeless billing reminders

Nothing kills momentum like a subject line that says, “Your subscription order is about to renew.”

That kind of transactional messaging doesn’t add value. It triggers anxiety. It gives people a reason to think, “Wait, do I still want this?”

Billing reminders are one of your best opportunities to talk to customers. Use them to remind people why they subscribed in the first place. Whether it’s ethically sourced ingredients or the freshest coffee in the game, lead with that value.

Most modern subscription platforms now offer quick actions directly in the email. Add buttons to skip, delay, or swap; the actions people actually want. Don’t just funnel them to a subscription portal where the cancel button is front and center.

If you're using Zaymo or another embedded experience tool, you can make that email feel like a concierge service, not an invoice.

3. No splash screen or video in the cancel flow

If your cancellation flow doesn’t have a splash screen with a video, you're leaving subscription saves on the table.

I’ve seen brands go from a 5% save rate to 16% just by adding a short video. Another client saw a jump to 23% by adding a simple splash screen that offered to delay before asking for cancellation reasons.

It doesn’t have to be fancy. A 60-second video from the founder talking about why the brand exists, what subscribers get, and what they’ll miss out on. You can also include options to skip or delay right there, before they even choose a cancel reason.

Want an AI prompt for your own founder video? Grab this guide for free.

This humanizes your brand at a key decision point. It can literally save thousands in revenue every month.

If you fix just one of these three things before the holiday rush, your subscription metrics will thank you. If you fix all three, you’ll head into Q4 with more momentum than you’ve had all year.

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

 - Matt Holman 🩺

The Subscription Doc