Dose #172: How a Baking Box Solved Subscription Clutter

Matt here with your weekly Subscription Prescription 💊

We’ve all seen monthly subscriptions that go unused and pile up around the house. In this week’s dose, we dive into how one brand took that problem and pivoted into an opportunity. We also dive into cross-selling and SMS strategies to improve retention.

This week’s dose is also a full interview with Shelley Gupta, the founder of Bakit Box. Listen to us on your favorite platform:

🩺 Boost Retention by Breaking the Monthly Box Model

Most subscription brands are afraid to touch the cadence of their deliveries. Changing the frequency of fulfillment can feel like messing with your entire business model. But sometimes, that’s exactly what your customers need.

This week I talked with a brand that made a bold switch—moving from monthly to quarterly—and saw stronger engagement as a result. That change unlocked some deeper insights about retention, product strategy, and customer communication that are worth exploring, no matter what kind of subscription you run.

Here are three big takeaways from the conversation:

1. Quarterly Fulfillment Can Actually Increase Engagement

Monthly shipments seem like a standard default. But for many families, especially those juggling education and parenting, monthly just becomes too much.

Bake It Box found that sending one box every month created a sense of clutter. Kits were piling up before they were being used. So they made a counterintuitive move: they switched to quarterly fulfillment, with each shipment including three different projects. This gave customers flexibility and reduced overwhelm. And the result? People were more likely to complete the kits.

The lesson here is simple. Just because you can ship every 30 days doesn’t mean you should. A slower cadence—when paired with the right kind of value—can actually lead to higher product usage and better retention.

2. Cross-Selling Works Best When It Reflects the Subscription Value

There are a lot of brands trying to cross-sell one-time purchases from their subscription box, but many fall flat because the products feel disconnected. Bake It Box approached this differently. After each quarterly bundle sells out, they make the most popular project from that kit available for one-time purchase—and they include all of the educational content that came with the original subscription.

This strategy does two things well. First, it introduces the brand to new customers in a way that feels consistent with the core subscription experience. And second, it lets existing customers continue engaging with the brand even if they’re not ready to commit to a full subscription again.

If you're struggling with what to offer as a one-time purchase, ask yourself: what part of your subscription is the most fun, most visual, or most likely to get shared? That’s the part to spin out.

3. Content-Driven SMS Isn’t Just for Selling

I’ve talked to a lot of brands that are scared to text their customers. They worry about being too aggressive, too invasive, or too annoying. But I believe the problem isn’t the channel—it’s the content.

Bake It Box uses post-purchase SMS to send helpful reminders, educational content, and creative prompts to keep customers engaged. And it works. They’re seeing high engagement rates and low opt-out rates. Not because they’re sending discounts, but because they’re sending value.

If your brand delivers anything that requires some kind of usage, habit, or education, SMS is a great way to make sure customers are actually getting the benefit of what they paid for. And when they do, they’re a lot more likely to stick around.

Retention doesn’t always come from more emails or bigger discounts. Sometimes it comes from rethinking your cadence, simplifying your message, and making it easier for customers to succeed with the product you’ve already sold them.

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

 - Matt Holman 🩺

The Subscription Doc