In this episode of The Orita Podcast, Aaron Schwartz sits down with Zach Scheimer, Senior Retention Marketing Manager at Criquet Shirts, for a masterclass in modern retention, where data meets brand, and CRM is more than just sending emails.Zach’s path to retention isn’t typical. From NFL mascot to stand-up comic to deeply technical email architect, he brings a rare blend of analytics, humor, and systems thinking to the craft. And it shows.Together, they unpack:• From mascot to marketer, how an unconventional background shaped Zach’s retention mindset• Data over opinions, why “the numbers are telling you something” is his core philosophy• Beyond email, how retention now spans SMS, direct mail, onsite experience, loyalty, and returns• The micro vs. macro lens, why customer service and retention are solving the same problem• Creative as the overlap, how brand voice fuels both performance and retention• Loyalty & exclusivity, why your best customers want to feel “in the club”• AI on-site, how product comparison agents could reshape customer experience• SMS & RCS, why richer mobile messaging is the next unlock• The hidden risk of over sending, and how channel fatigue quietly kills long-term valueIf you care about customer lifetime value, cross-channel alignment, or building a retention engine that actually respects the customer, this one’s for you.👥 Meet the guestZach Scheimer, Senior Retention Marketing Manager at Criquet Shirts🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters05:32] Retention’s Secret Weapon: Technical Skills Most Marketers Don’t Have[08:24] Why Your Emails “Underperform”[11:11] The Naming System That Turns Your CRM Into a Money Dashboard[14:00] How Criquet’s Brand Voice Makes Customers Feel Like Insiders[16:46] Personalization Without Being Creepy: The Line Every Brand Crosses[17:40] Retention Isn’t Email Anymore: The New Tool Stack (and New Rules)[20:29] Loyalty That Works: Exclusivity vs. Points[22:11] The Customer Journey Isn’t Linear: Here’s How Criquet Designs It[24:48] Performance vs. Retention Is a False War (Creative Is the Bridge)[27:42] Stop Retargeting Recent Buyers: The Simple Fix Most Brands Miss[30:41] Gmail AI Summaries + RCS: The Next Wave Coming for CRM[34:34] Marketing + CX: The Teams That Don’t Talk Are Bleeding Revenue[37:03] AI on Your Site: The Shopping Assistant That Could Replace “Where Do I Click?”🌐 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📩 Subscribe for more founder‑grade retention intel