Dose #193: Education, Cross-sells, and Winbacks

Matt here with your weekly Subscription Prescription 💊

A big part of retention is timing. Not just how often you communicate, but what and when. In this week’s dose, we dive into some critical pieces of the subscription retention puzzle: education, timely upsells, and winbacks.

This week’s dose is also a full podcast interview with Jade Moffatt from Dirtea. She’s a killer retention expert with a background in CX, so listen in or watch on your favorite platform:

Let the Paper Run

Paper Run has reimagined direct mail specifically for subscription brands. It helps brands like Grüns, Neuro, Create, Ancestral, Heights, Spacegoods, and many more identify, reach, and convert customers who aren’t opening their emails by sending them physical mail.

In a world where email and SMS are can no longer be relied on to reach every customer, subscription brands are turning to Paper Run en masse to pick up the slack.

With native integrations in Recharge, Autoship Cloud, SKIO, Stay AI, and Loop, Paper Run helps brands build automated, measurable direct mail flows that print and deliver every day - ensuring brands can always get the right message to the right people at the right time.

How subscription brands are using Paper Run:

• Win back cancelled subscribers who can’t otherwise be reached

• Increase second-order rates for one-time purchase (OTP) customers with replenishment reminders

• Retarget abandoned carts, checkouts, and site visitors who can’t otherwise be reached

Paper Run is making direct mail one of the easiest wins for subscription brands in 2026. For a limited time, Subscription Prescription readers receive 20% off Paper Run. Just let them know how you heard about them to receive the discount!

This was one of my favorite interviews in recent memory because of Jade’s CX background and perspective. So, let’s dive into some critical retention touchpoints and how you can do a better job managing subscriber experiences to improve LTV>

Educate First, Sell Second

Dirtea sells functional mushroom products. That means most new subscribers don't fully understand what they bought. They don't know how long it takes to feel the effects. They don't know the best way to use the product. And they definitely don't know how different products in the range work together.

So Dirtea made education the foundation of their entire onboarding experience.

Before they pitch a second product or ask for a review, they make sure every subscriber understands what they're taking, why it works, and what to expect. That means setting realistic timelines, explaining the science in plain language, and reinforcing the value of consistency.

This matters because most subscription churn happens when customers don't feel a result fast enough. If you haven't set expectations upfront, silence fills the gap. And silence leads to cancellation.

Takeaway: Your onboarding flow should answer every question a new subscriber might have before they think to ask it. Education is your first retention tool.

Timing Your Cross-Sell

One of the smartest things Dirtea does is wait.

They don't try to cross-sell a second product during onboarding. They don't bundle upsells into the first order confirmation. They wait until a subscriber has completed at least one full cycle before introducing anything new.

Why? Because a customer who hasn't experienced the value of their first product isn't ready to buy a second one. Pushing too early feels pushy. Worse, it distracts from the education process that's keeping them subscribed in the first place.

Once a customer has gone through their first cycle, they understand the product. They've seen the results. Now a cross-sell feels like a natural next step, not a cash grab.

Their CX team plays a big role here too. Before any retention or cross-sell messaging goes out, the CX team reviews it. They act as a sense-check, making sure the messaging reflects what customers are actually saying and feeling. It's a simple step that keeps their communication grounded in reality rather than marketing assumptions.

Takeaway: Don't rush the cross-sell. Let customers experience value first. And use your CX team as a filter for every piece of retention messaging you send.

Winbacks That Actually Make Sense

Most winback flows are generic. Someone cancels, they get a discount email a week later. Dirtea does it differently.

They segment their winback flows by two variables: the reason someone cancelled and the product they were on. That changes everything.

A customer who cancelled because they had too much product gets a different message than someone who cancelled because they didn't see results. A customer on their Lion's Mane subscription gets different messaging than someone on their Reishi blend.

This level of segmentation means their winback messages actually feel relevant. They're not blasting a 20% off code and hoping for the best. They're addressing the specific reason someone left and offering a specific path back.

And for the customers they can't reach by email? That's where Paper Run comes in. Dirtea uses direct mail to re-engage churned subscribers and customers who've opted out of email and SMS entirely. The result: a 200% lift compared to their digital-only winback flows.

When your best retention channels can't reach someone, you need a way through the front door. Physical mail does that.

Takeaway: Segment your winback flows by cancellation reason and product. Generic "come back" emails don't work. Relevant, specific messaging does. And when digital channels fail, direct mail picks up the slack.

Bottom Line

Dirtea's approach isn't flashy. It's methodical. Educate new subscribers so they stay. Time your cross-sells so they feel like value, not a pitch. Segment winbacks so they convert. And use direct mail when digital channels can't reach people.

Every touchpoint in their system includes a feedback loop. Every message gets checked by the people who talk to customers every day. That's how you build retention that compounds over time instead of relying on discounts to plug the gaps.

The brands that win at retention aren't the ones with the cleverest tricks. They're the ones that understand their customers well enough to talk to them like humans.

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

 - Matt Holman 🩺

The Subscription Doc