#364 - Cracking the Code on Retention: Recharge CEO Reveals What Best-in-Class Subscription Brands Do Differently

Oisin O'Connor is the CEO and co-founder of Recharge, the leading subscription management platform powering 75% of all Shopify subscriptions. Under his leadership, Recharge has become a critical infrastructure partner for over 30,000 brands, reaching 100 million subscribers and $100 million ARR. In this episode of DTC Pod, Oisin pulls back the curtain on what it really takes to win with subscriptions in today’s DTC landscape. He shares insider strategies for subscriber growth, optimizing retention, and leveraging Recharge’s newest AI-powered tools to minimize churn. Oisin also shares specific benchmarks every brand should measure, real-world examples of subscription funnels that convert, and actionable experiments operators can run to unlock long-term profitability and scale. Episode brought to you by Stord Interact with other DTC experts and access our monthly fireside chats with industry leaders on DTC Pod Slack. On this episode of DTC Pod, we cover: 1. Evolution of subscriptions in physical product e-commerce 2. How to spot and create product-market fit  3. Differentiators that set Recharge apart from early competitors 4. The compounding power of subscriptions for long-term growth 5. Unit economics, LTV vs CAC, and why retention is king 6. What best-in-class subscription brands do differently 7. Optimizing conversion funnels for subscriber growth 8. Subscription benchmarks: churn rates, retention, and second order metrics 9. Reducing churn with data, cancellation flows, loyalty, and rewards 10. Automations and integrating Recharge with supply chain and 3PL operations 11. Leveraging AI Concierge for customer retention and support 12. Evolving customer experience and the need for seamless subscription management 13. How Recharge guides merchants with data, support, and innovation 14. Experiments and mistakes founders make launching subscription brands Timestamps 00:00 Oisin’s background, founding story, and early agency experiments 04:06 The rise of Shopify and the breakthrough with Recharge 05:19 The subscription model: initial skepticism and quirky early adopters 06:47 Technical challenges in enabling subscriptions on Shopify 09:00 First major subscription brand success story 10:15 Compounding growth through subscriptions 11:36 Legacy brands and decades-long customer retention 13:06 Building DTC businesses with sustainable unit economics 14:37 Lessons from TV advertising history and the narrowing of scalable models 16:29 Key traits of successful subscription businesses 17:09 Product, recurring need, and conversion strategy 18:27 Understanding subscriber value and optimizing acquisition 19:26 Retention: keeping customers post-acquisition   19:52 High-performing brands and funnel design 20:05 Subscription by default, offers, upsells, and cross-sells 21:39 Conversion tactics from PDP to post-checkout 22:38 Benchmarks for healthy churn and retention 23:06 How top brands reduce churn and track performance 24:58 Recharge tools: analytics, cancellation flows, Klaviyo integration 26:41 Rewards and automations to boost retention 27:33 Automate flows for backend fulfillment and logistics 28:20 Launching AI SMS concierge for subscriber experience 29:40 Reducing customer service friction and delighting shoppers 32:15 Customer experience as a core differentiator 34:04 The competitive subscription landscape: Recharge’s position 35:41 Product innovation, support, and actionable guidance 37:16 Data-driven product innovation and merchant success 38:04 The future of subscription, retention, and platform innovation 40:38 Biggest mistakes founders make with subscriptions 41:58 Experiments founders should run with Recharge 42:58 Where to connect with Oisin for advice and mentorship Show notes powered by Castmagic Past guests & brands on DTC Pod include Gilt, PopSugar, Glossier, MadeIN, Prose, Bala, P.volve, Ritual, Bite, Oura, Levels, General Mills, Mid Day Squares, Prose, Arrae, Olipop, Ghia, Rosaluna, Form, Uncle Studios & many more.   Additional episodes you might like: • #175 Ariel Vaisbort - How OLIPOP Runs Influencer, Community, & Affiliate Growth • #184 Jake Karls, Midday Squares - Turning Your Brand Into The Influencer With Content • #205 Kasey Stewart: Suckerz- - Powering Your Launch With 300 Million Organic Views • #219 JT Barnett: The TikTok Masterclass For Brands • #223 Lauren Kleinman: The PR & Affiliate Marketing Playbook • ​​​​#243 Kian Golzari - Source & Develop Products Like The World's Best Brands ----- Have any questions about the show or topics you'd like us to explore further? Shoot us a DM; we'd love to hear from you. Want the weekly TL;DR of tips delivered to your mailbox? Check out our newsletter here. Projects the DTC Pod team is working on: DTCetc - all our favorite brands on the internet Olivea - the extra virgin olive oil & hydroxytyrosol supplement Castmagic - AI Workspace for Content Follow us for content, clips, giveaways, & updates! DTCPod Instagram DTCPod Twitter DTCPod TikTok Oisin O'Connor - Co-Founder and CEO of Recharge Blaine Bolus - Co-Founder of Castmagic Ramon Berrios - Co-Founder of Castmagic