Dose #141: From Teacher to Ecommerce Success

Matt here with your weekly Subscription Prescription 💊

You can learn a lot from how other businesses grow. In this week’s dose, we dive into how Learning with Kelsey grew from a neighborhood business to one with thousands of subscriptions online. With a great offer, flexible subscription, and products that solve a real need.

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

Strengthen your subscription with better fulfillment

Earning a subscriber is only the first step in a delicate dance to repeatable revenue. If you are a subscription service with a physical product, everything hinges on if you can get the correct product to your end consumer on time, every time.  If you are not properly equipped to manage your subscription fulfillment, you will lose your customers to your competitors.

By 2026, the global e-commerce subscription market size is expected to reach $904.28 billion, at a compound annual growth rate of 65.67%. That is a lot of potential new and returning customers that will demand flawless fulfillment. Stord, a commerce enablement fulfillment and technology company, specializes in subscription fulfillment for some of the leading supplement and beauty brands - delivering millions of orders per month for their eager customers. Stord has built custom tools specifically for subscription businesses, including order routing, first-order upgrades, kitting, and multi-inventory management.

Take the mystery out of your entire subscription customer experience with a custom analysis by Stord.

How Learning With Kelsey Built a Subscription That Keeps Growing

Every subscription business wants more growth. But real, sustainable growth comes from more than just spending on ads—it starts with a great offer, a flexible subscription model, and an experience that keeps customers engaged.

This week, I had the chance to talk with Kelsey Cook, founder of Learning With Kelsey, a fast-growing subscription box for parents who want hands-on, educational activities for their kids. What started as a way to help local families during the pandemic has turned into a thriving business.

After seeing how she’s scaled while keeping customers happy, there are some big lessons every subscription brand can take away.

1. The Offer Has to Be More Than Just a Discount

A lot of brands make the mistake of assuming a simple "subscribe and save" discount is enough to drive conversions. But customers need a clear reason to subscribe—especially when they could just buy a product one time.

What Learning With Kelsey does right:

• It’s a complete experience, not just a product. Parents don’t just get supplies—they get fully planned-out activities, instructions, and everything they need to make learning fun.

• Each box is unique. Unlike many subscriptions that repeat the same products, every month brings new themed activities—so subscribers have a reason to stay engaged.

• It solves a real problem. Instead of spending hours searching Pinterest or buying supplies separately, parents get a simple, done-for-you solution that makes learning at home easy.

If you’re struggling to convert subscribers, ask yourself: Is my offer just a discount, or am I making my subscription the best way to buy?

2. Subscription Flexibility Keeps Customers Longer

One of the biggest reasons people cancel subscriptions? They outgrow them. If you don’t have a plan to keep customers engaged over time, churn will always be an issue.

How Learning With Kelsey solves this:

• A clear upgrade path. Customers don’t just cancel when their child ages out of a box—they move up to the next level (Toddler → Preschool → Kinder Prep).

• Customizable options. Parents can switch to different boxes as their child’s needs change, keeping them in the subscription longer.

• Built-in engagement. Parents don’t just get a box—they get a system for ongoing learning, which makes the subscription feel essential instead of optional.

A well-designed subscription gives customers reasons to stay—not just reasons to sign up. If you’re seeing high churn, consider whether your product evolves with your customers.

3. Great Marketing Can’t Fix a Bad Product Experience

Some brands try to scale before they’ve nailed the subscriber experience. But a strong product fuels word-of-mouth growth—and that’s exactly what helped Learning With Kelsey take off.

Here’s what they do well:

• An engaging unboxing experience. Every box feels exciting to open—kids get themed activities, not just a collection of random items.

• Customer-driven improvements. Kelsey built the Toddler Box after hearing that younger siblings wanted to join in, and it’s now their most popular product.

• Authentic community building. Happy customers share their kids’ experiences on social media, driving organic growth without massive ad spend.

If your subscription isn’t growing as fast as you want, ask yourself: Are customers excited to receive each box? If not, no amount of marketing will fix that.

Final Thoughts

Learning With Kelsey’s success comes down to three things: a strong offer, built-in flexibility, and an experience that keeps customers engaged. These are the fundamentals that turn a subscription into something customers want to stick with—month after month.

That’s it for this week’s dose—see you next Tuesday for #142!

 - Matt Holman 🩺

The Subscription Doc