Dose #155: Reimagining Popups

Matt here with your weekly Subscription Prescription 💊

This week we’re talking popups—but not the annoying kind. I’m breaking down how smarter popup strategies can boost opt-ins, increase subscription take rate, and unlock the kind of customer data that makes your entire lifecycle marketing sharper.

This week’s dose is also an interview with Shaan Arora, a cofounder of Alia, a great popup tool. Listen to us dive into more examples of how this works, so tune in or watch on your favorite platform:

🧠 Smarter Popups, Stickier Subscribers

We’ve all heard the phrase “the money’s in the list.” But the real money? It’s in knowing why someone joined your list in the first place. This week I want to break down a better way to think about popups and how to make them work harder — not just to collect emails, but to actually set up better customer journeys and stronger subscriptions.

Because let’s be honest: generic “10% off” popups just aren’t cutting it anymore.

1. Use Popups to Learn, Not Just to Bribe

If you’re only using your popup to offer a discount in exchange for an email, you’re missing a massive opportunity. Asking a simple question like, “Who are you shopping for today?” before you even show the discount actually increases opt-in rates. It sounds counterintuitive, but this early engagement primes the customer. It gives them a reason to stop and think, not just skim and close.

And when you start learning something — even one key trait — about that customer in the first 5 seconds, you can do so much more with every message you send afterward. Whether they’re buying protein to bulk or slim down, matcha as a health swap or for the ritual — the follow-up content shouldn’t be the same.

2. Let Zero-Party Data Shape the Entire Experience

The magic here isn’t just about better open rates or higher opt-ins. It’s about creating segments and flows that actually speak to what customers care about. I’ve seen brands ask about goals, preferences, even emotions — “Why are you trying to lose weight?” is more powerful than “What’s your favorite flavor?”

And it doesn’t stop at welcome emails. Great brands are tagging these responses and reusing them 3, 6, 12 months later when they release new products, send billing reminders, or fight churn. “You told us you love matcha — here’s a new ceremonial-grade drop just for you.” That’s relevance at scale.

3. Get Granular — Because Popups Should Drive Revenue, Not Just Emails

Let’s kill the myth that popups are only a list-building tool. If you’re not measuring the AOV or conversion rate of popup-engaged users, you’re flying blind. The best brands I work with treat their popup flows like mini customer onboarding tools. They use boosted discounts as a reward after answering a few quick questions — which increases conversion, raises AOV, and creates a stickier first-time experience.

And the difference in behavior? Night and day. When someone answers 2–3 questions and gets a “custom” offer or product recommendation, they’re mentally invested. They convert more, they retain better, and they’re more likely to see themselves in your brand’s mission.

If you’re serious about building a stronger subscription program, don’t ignore your popup. It’s not just about capturing traffic — it’s your first and best shot to start a conversation, get context, and lay the foundation for a longer, more profitable customer journey.

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

 - Matt Holman 🩺

The Subscription Doc