Customer Retention: How Subscription Attracts & Retains More Customers with Matthew Holman, Subscription Prescription (episode 246)
by Chloe ThomasMatthew Holman runs Subscription Prescription and is obsessed with getting subscription eCommerce right. Helping brands via his newsletter, podcast and fractional subscription leadership consulting.

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Dive in:
[05:12] Subscription isn’t just retention.
[08:35] Subscription strategy debate.
[09:29] Boosting subscription conversions strategies.
[15:26] Enhancing subscription offers effectively.
[18:12] Discount strategy beyond price cuts.
[20:38] Effective email engagement strategies.
[24:48] Maximize value from super customers.
[27:51] Insider Tips from Matthew!
The Right Offer Can Make or Break a Subscription Business
The way you present a subscription offer has a huge impact on conversions and retention. Matthew emphasizes that brands should test different structures, like offering monthly, quarterly, or annual plans. Providing incentives, such as a free gift instead of a discount, attracts the right customers who are more likely to stay. He also suggests defaulting to a subscription at checkout while making the terms crystal clear. A well-crafted offer not only increases sign-ups but also ensures customers stick around longer.
Onboarding is the Secret to Retention
Getting customers to use the product right away is key to keeping them subscribed. Matthew says that many people cancel because they never started using the product. Brands should send welcome emails, provide step-by-step guides, and expect common questions. A simple instruction card in the package can make a big difference. The more engaged a customer is in the first 14 days, the less likely they are to cancel.
Focus on Your Best Customers, Not Just Stopping Churn
Instead of obsessing over lost customers, businesses should nurture their most loyal ones. These “super customers” will buy more, refer others, and support new product launches. Matthew suggests offering VIP perks, exclusive products, or longer-term subscription plans to reward them. SaaS companies do this well by constantly improving features for their power users. Brands that focus on keeping their best customers happy will naturally see higher retention and lifetime value.
Listen to hear Matthew’s Insider Tips on Retention!
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