In this episode of The Orita Podcast, Aaron Schwartz sits down with Zac Cherin (Partner at Simplistic, Founder at Hiro) and Max Sturtevant (Founder at WellCopy) to dissect what the best retention agencies are really doing and what most brands are still getting wrong.

They break down:

• Pop-up psychology, mystery discounts, and why most forms kill conversions

• Offer-first thinking, and how creative testing beats personalization for 99% of brands

• Signal disruption, from plain text emails to refund lotteries and gifting funnels that actually work

• Tech that matters, and what AI tools they’re watching (or avoiding) going into 2026

• Rethinking BFCM, and why owning your own holiday might beat chasing Black Friday hype

This one is full of hard-won tactics, honest advice, and actual data from hundreds of brands. Whether you run a lifecycle team or hire one, this is a must-listen on doing more with less and keeping your edge in a noisy, copy-paste world.

👥 Meet the guests

Zac Cherin: Partner at Simplistic | Founder of Hiro | Lifecycle & tech strategy leader

Max Sturtevant: Founder, WellCopy | Retention agency scaling 100+ brands with pure email performance

🎙 Hosted by Aaron Schwartz, Co-Founder & Co-CEO, Orita.ai

🎧 Chapters [00:00] How Two Top Retention Agencies Actually Work Behind the Curtain [02:40] Content That Converts: What Still Works and What’s Dead [05:33] What Makes a Real Retention Agency (Not Just Another Klaviyo Shop) [08:26] Why Most Agencies Just Copy-Paste, And How to Be the Exception [11:00] Personalization Myths: When “Relevant” Becomes Irrelevant [13:40] Email Isn’t Dead, It’s Just Been Boring (Until Now) [16:32] Pop-Ups That Don’t Suck: Offers, Triggers, and Tactics That Work [19:22] Retention v Performance: How to Make Them Work Together [24:51] 2026 or Bust: The New Rules of Agency Positioning [27:01] Why Brand CMOs Are Taking the Wheel [30:02] Retention in Recession: What’s Actually Working in a Tight Market [32:47] Signal Disruption: The Anti-Trend That’s Driving Results [36:51] The AI We Use and the Tools We’ve Stopped Believing In [39:52] Stop Reporting Fluff: The Metrics That Actually Matter 43:53] How to Keep BFCM Customers From Ghosting in January

🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when.

🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai

🎧 Listen on Spotify & Apple

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