Dose #194: The Email Strategy You're Getting Backwards

Matt here with your weekly Subscription Prescription 💊

One of the biggest mistakes I see in subscription retention is email strategy. Often, it’s a complete lack of strategy, but most of the time it’s a misunderstanding with what is effective for new subscribers. Onboarding, great billing reminders, and opting new subscribers out of ongoing campaigns.

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This week I'm picking a fight with your email agency.

I see this pattern constantly when working alongside email teams on subscription programs. The standard playbook for subscriber communication is almost always wrong. Not because email agencies are bad at what they do. They're great at campaigns, abandoned carts, and browse abandonment flows. But subscription retention is a different animal, and most agencies treat it the same as everything else.

Here are three things I think most brands get backwards when it comes to email and subscriptions.

Your onboarding emails are too spread out.

The typical play is a welcome email after purchase, then something a few days later, then another one 10 to 15 days out. The logic is that you don't want to overwhelm new subscribers.

I think that's nonsense.

Here's why: the most important thing after someone subscribes is getting them to actually use the product. And that window is narrow. They're excited when they buy. They're excited when the product arrives. That's maybe two to six days depending on your shipping times.

After that? Motivation drops off a cliff.

So I want to send an email every single day between purchase and delivery. A welcome email 10 to 15 minutes after checkout. Then daily touchpoints covering things like:

• Why your product is different (and worth the price)

• How to use it properly

• What to expect and when

• Your founder story and brand mission

Once the product is delivered, send one or two messages about usage and consumption. Then leave them alone.

Yes, any individual email can cause churn. You're reminding people they have a subscription, and some of them will cancel. But the right test isn't "did this email cause cancellations?" The right test is "did this cohort retain better into month two, three, and four?"

And the answer is almost always yes. A strong onboarding series improves renewal rates across the board, even if individual emails trigger some early churn.

Takeaway: Front-load your onboarding emails into the excitement window. Test the whole series against overall retention, not individual email performance.

Your billing reminder email is doing nothing for you.

This one frustrates me. The billing reminder is the single biggest piece of real estate you have to re-sell someone on their next renewal. And most brands treat it like a transactional receipt.

"Your order is renewing in 3 days. Here's what you'll be charged."

That's it. No benefits. No reinforcement. No reason to stay.

Your email agency probably built this once and never touched it again because they're busy optimizing campaign flows. But this email goes to every active subscriber before every renewal. That's an enormous opportunity.

If people cancel because of cost, use this email to reinforce value. If people are skeptical the product is working, remind them what to expect and how long it takes. If your product has a compelling story, tell it again.

The billing reminder should feel aspirational, not transactional. It should remind people why they subscribed in the first place.

Takeaway: Audit your billing reminder email this week. If it reads like a receipt, rewrite it as a retention tool.

You're afraid of SMS but not afraid of daily promo blasts.

This is the weirdest paradox I come across. A brand tells me they don't want to send billing reminders because it might cause churn. But that same brand keeps every subscriber in their daily campaign flows getting emails about sales, new products, and promotions.

Think about that. You won't remind someone their subscription is renewing, but you'll email them every day trying to sell them something new.

If you're worried about over-communicating, start by opting subscribers out of general campaigns for month one or two. Then look at building campaigns specifically for subscribers. They're your warmest audience. They deserve offers designed for them, not the same blast going to your 120-day active list.

Things like quick-action links to add a product to their next order. Or subscriber-exclusive pricing on new products. These convert better and they solve the "how do I run a 50% off sale without losing my subscribers" problem.

And on SMS specifically: I've seen it work as a retention tool over and over again. SMS gives subscribers control. They can delay, swap a flavor, or adjust frequency without ever seeing a cancel button. Our research across hundreds of thousands of subscriptions showed that subscribers who make frequency changes have higher LTV. SMS is the best way to enable those changes.

Takeaway: Stop treating subscribers the same as your general list. Build subscriber-specific campaigns and consider SMS as a control tool, not a churn risk.

Bottom Line

The conventional email wisdom for subscriptions is too conservative in the wrong places and too aggressive in others. Front-load onboarding. Transform your billing reminder. Be strategic about campaigns. And don't be afraid of SMS.

Everything I laid out here is testable. Run the A/B tests. Look at cohort retention, not individual email metrics. And if you've seen something work differently, I genuinely want to hear about it. Reach out on LinkedIn or email me at [email protected].

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

 - Matt Holman 🩺

The Subscription Doc