Dose #143: To Send or Not to Send, That is the Question [Upcoming Billing Reminders]

Matt here with your weekly Subscription Prescription 💊

Many growing subscription brands don’t send an upcoming billing reminder. They don’t do it to keep churn lower than it would be had you not sent it. In this week’s dose, we dive into why that short-sighted behavior is costing you money.

This week’s dose is also a full podcast interview! Give it a listen on YouTube, Apple Podcast, or Spotify:

Why Sending Billing Reminders is Better for Your Business

This week, I’m tackling a common debate: Should you send an upcoming billing reminder to subscribers—or skip it to avoid cancellations?

Some brands worry that sending these emails will remind customers to cancel, so they opt out of sending them altogether. But based on everything I’ve seen in subscription businesses, sending billing reminders the right way actually leads to higher lifetime value (LTV) and fewer chargebacks. Let’s break down why.

1. The Chargeback & Customer Service Nightmare

If you don’t send a billing reminder, your customers still get a notification—it just comes in the form of an order confirmation or a surprise charge on their credit card. And when that happens, three things can go wrong:

1️⃣ They contact customer service, frustrated, asking for a refund. Best-case scenario, you issue a refund and lose revenue. Worst case? The product has already shipped, and now you’ve lost fulfillment costs too.

2️⃣ They file a chargeback. Chargebacks aren’t just a lost sale—they damage your payment processing health, increase declined transactions in the future, and in some cases, customers can successfully dispute multiple months at once.

3️⃣ They cancel immediately. Without a proactive message from you, they’re just reacting to a charge they weren’t expecting. This means they’re less likely to accept retention offers and more likely to leave for good.

Skipping billing reminders might delay churn, but it doesn’t prevent it. And when those cancellations do come, they’re often more damaging.

Important Question: If you’re not tracking how many people ask for a refund after their order processes, do you even know if you’re getting a net revenue bump by not sending them?

2. The Missed Opportunity to Drive More Revenue

A billing reminder isn’t just a notice—it’s a touchpoint to engage with subscribers before they make a decision about their next order. If you’re not sending one, you’re also missing a chance to:

• Remind them why they subscribed in the first place. A message like "Another month of better sleep is on its way!" reinforces value, instead of just saying "Your order is processing soon—click here to manage your subscription."

• Offer self-service options. Tools like Zaymo let customers adjust frequency, skip a month, or swap products without ever seeing a cancellation button. If you’re worried about churn, give customers better control instead of keeping them in the dark.

• Drive upsells and upgrades. I’ve seen brands increase LTV significantly by using billing reminders to offer product add-ons or upgrades to longer subscription commitments (like switching from monthly to quarterly).

If you avoid sending billing reminders to "hide" the subscription from customers, you’re also hiding the revenue-generating potential of that email.

3. The Best Subscription Brands Send Billing Reminders

Some growing brands avoid billing reminders because they see a spike in cancellations when they send them. But here’s the truth: Larger, more successful subscription brands send billing reminders.

Why? Because higher LTV beats short-term revenue bumps.

If your churn rate is already high, avoiding a billing reminder won’t fix that—it just delays the inevitable. Instead of worrying about short-term cancellations, focus on building a better customer experience that:
✅ Makes it easy to adjust frequency instead of canceling
✅ Creates upsell opportunities inside the billing reminder
✅ Reinforces why the subscription is worth it

And for those who are going to churn? They’ll cancel either way—you just get to decide whether they cancel before the charge (where you can influence their decision) or after (where you have little control).

Final Thoughts

At the end of the day, the goal isn’t just to keep subscribers for one extra month—it’s to maximize LTV and create a better customer experience. And sending well-crafted billing reminders is one of the easiest ways to do that.

If you’re currently avoiding them because of cancellation fears, test a smarter approach:
1️⃣ Improve the messaging so it reinforces product value
2️⃣ Add self-service options so customers can skip instead of cancel
3️⃣ Include an upsell offer to capture more revenue before the charge

Want help optimizing your billing reminders? Reply to this email or send me a DM—I’m happy to share examples that work.

That’s it for this week’s dose—see you next Tuesday for #144!

 - Matt Holman 🩺

The Subscription Doc