Deciding What to Put Behind a Paywall

On the podcast, I talk with Michael about the blessing and curse of having a brand, why post-purchase is the perfect upsell moment, and why partnerships are hard to pull off but can be well worth the effort.

Top Takeaways:

🌱Growth is Built on Value
Sustainable growth comes from consistently adding value, not just short-term tactics.  Success lies in constantly evolving your product to meet users' needs. By regularly introducing new features and improving the user experience, premium products remain relevant and compelling. That value is continuous, with acquisition and retention working together to drive long-term growth.

🎯 Personalize for Retention
 Different users have different goals, and understanding this is key to retention. Tailor offerings to specific user needs, whether it is job seekers, hobbyists, or niche audiences. By tailoring plans and features to user intent, brands can keep their products relevant. Without this personalization, users may disengage and churn.

📊 Test to Optimize
With hundreds of A/B tests each year, Condé Nast learns what works quickly. Data replaces debate, helping the team iterate faster. The goal is not just to optimize, it is to foster a culture of constant learning and growth.

🔄 Retention Is a Journey
 Churn does not always mean goodbye. Many users return later when their needs change. Offering win-back deals, fresh trials, and adding new value helps bring users back and turn them into long-term subscribers. Retention is a process, not a straight line.

🤖 AI Supports, Not Leads
AI should enhance the user experience, not overshadow it. AI’s role is to solve problems, helping users find content or personalize their experience, while staying behind the scenes. The real value is in solving the user’s needs, not in the technology itself.

About Michael Ribero: 

👨‍💻 SVP, Global Consumer Revenue at Condé Nast.

📈 Michael leads the subscription and growth strategies for some of the world’s most iconic media brands, including Vogue, GQ, The New Yorker, and Wired. He focuses on optimizing user engagement, experimenting with monetization strategies, and evolving the digital experiences that drive both free and paid subscriptions.

💡 "We’ve learned that true growth comes from continually adding value. Our approach isn’t just about scaling; it’s about providing lasting benefits that evolve with our users’ needs."

👋 LinkedIn

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• David Barnard - @drbarnard
• Jacob Eiting - @jeiting
• RevenueCat - @RevenueCat
• SubClub - @SubClubHQ

Episode Highlights:
[0:00] Why launching a premium tier isn’t always the right move
[2:51] Competing with AI-native upstarts and influencer content
[5:39] Media's frenemy dynamic with platforms like Meta
[8:25] Balancing free vs. paid content without eroding brand trust
[11:46] How to recover from a failed paywall experiment
[13:23] What bundling and post-purchase upsells look like at Condé Nast
[19:41] Real-world LTV boosts from zero-CAC upsell moments
[22:30] Lessons from low-priced tiers like the Washington Post’s Starter Pack
[26:07] Tiering vs. focus: when a premium plan is actually a distraction