Dose #176: Retention Strategy, Not Just Tactics

Matt here with your weekly Subscription Prescription 💊

This week’s dose is all about strategy and reducing complexity. You need more than just someone to ‘do the work.’ You need someone to analyze, think, and plan! We also dive into oversegmentation, and how you can never really do too much education for your subscribers.

This week’s dose is also a full podcast interview with Sonja Grasser from Wellbel. Listen in on your favorite platform:

🎯 Retention Strategy, Not Just Tactics

Most brands think they need an operator when what they really need is a strategist.

Retention isn’t just email and SMS. It’s not just tweaking flows after the fact. If your entire retention plan is based on backend automations, you're going to miss the bigger picture and leave a lot of money on the table.

After working with dozens of brands on their subscription strategy, here are three things I’ve found that most brands are either missing completely or misunderstanding altogether:

1. You can’t operate your way out of a strategy problem

When headcount is tight, brands tend to hire doers. People who can write the emails, build the flows, and launch the campaigns. There’s nothing wrong with that, but if nobody’s thinking about how the whole retention system fits together, from acquisition quality, subscription setup, usage habits, upsell timing, and more, you’re going to end up spinning your wheels.

I’ve seen brands with a great product, strong CAC, and healthy traffic still fall flat because they weren’t connecting the dots. The strategy layer is what tells you where to look, why something isn’t working, and how to make it better. Without that, even the best operators are just patching holes without fixing the leaks.

Simple solution: look at fractional subscription leaders. You get an incredible bang for your buck, because they’ve worked with (or are working with) enough brands doing different things to have a clear view of what’s working.

Sonja, who we interviewed on this week’s dose, is one of those. Joe Siegel from a past episode as well. And, don’t forget to check out our friends at hirethestarters.com - they have a ton on that platform.

2. Most segmentation is wasted or nonexistent

It still surprises me how many brands send the same email to every subscriber on their list. No segmentation by behavior. No consideration for lifecycle. Not even a simple split between new and repeat buyers.

Everyone thinks that personalization and segmentation are this incredibly complex and sophisticated experience. You can do that, but I wouldn’t. You don’t need 27 segments to get started. But you do need at least three:

• Never purchased

• Purchased once

• Purchased more than once

From there, add timing. Someone who purchased once 10 days ago is very different from someone who purchased once 90 days ago. If you’re not tracking your time-to-second-purchase, you have no idea when that critical window is closing. Once they’re gone, they’re likely not coming back.

Start simple. But start segmenting.

3. Educate, remind, reinforce (and do it often)

If your customers aren’t hearing from you between charges, they’re forgetting why they subscribed in the first place.

Retention is a habit game. In CPG especially, the best way to reinforce value and reduce churn is by helping customers use the product. Tell them how it works. Show them how to get results. Remind them why they bought it in the first place.

The brands I see doing this well send weekly or monthly updates, or blog content to subscribers. Not salesy. Just useful. When your product becomes part of their routine, your subscription becomes harder to cancel.

Also: don’t be afraid of transactional emails. Renewal reminders and post-purchase surveys are underrated opportunities to drive engagement, gather insight, and build trust.

Getting retention right doesn’t mean having the flashiest flows or the lowest churn rate. It means having a plan that actually matches how your customers buy, use, and think.

If you’re only optimizing what happens after the sale, you’re already too late.

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

 - Matt Holman 🩺

The Subscription Doc