How To Craft A Winning Subscription Offer With Matt Holman

Sign up for ⁠⁠⁠our newsletter⁠⁠⁠ to get access to our template for AI prompts and the payback model template from last weeks episode. In this packed episode, Richie and Joe interview subscription expert Matt Holman about what's actually working in subscription ecommerce right now. Matt breaks down why the standard "subscribe and save 10%" model is the "bane of his existence" and reveals the strategies top brands are using instead. You'll learn why bulk options (30/60/90 day supplies) are driving higher AOVs AND better retention, why free gifts convert better than deeper discounts, and how smarter product page design can dramatically increase subscription take rates. Matt shares real examples from brands like Pretty Boy skincare and Jolie, explaining exactly how they've optimized their offers. Plus, get tactical insights on measuring subscription cohorts, analyzing LTV by offer type, and making smart decisions even with imperfect data. Whether you're just starting with subscriptions or looking to optimize your existing program, this episode delivers actionable strategies you can implement today. TIMESTAMPS (02:46) Introduction and Guest Welcome  (05:32) Subscription Offers: The Basics  (08:11) Optimizing Subscription Offers  (12:45) Case Study: Pretty Boy Skincare  (17:56) Incentivizing with Gifts  (23:20)  First-Order Profitability vs Long-Term LTV (26:30) Exploring Subscription Offers  (28:29) Try Before You Buy  (31:10) Designing Subscription Components  (34:49) Data-Driven Decisions  (40:26) Conclusion and Next Steps   Thank you to our sponsors ⁠⁠⁠AfterSell⁠⁠⁠  ⁠⁠⁠Parker⁠⁠⁠ ⁠⁠⁠Rivo⁠⁠ ⁠⁠⁠Postscript⁠⁠   Follow Richie (⁠⁠⁠X⁠⁠⁠ | ⁠⁠⁠LinkedIn⁠⁠⁠) and Joe (⁠⁠⁠X⁠⁠⁠ | ⁠⁠⁠LinkedIn⁠⁠⁠) for more e-commerce insights and to join the conversation.