In this episode of The Orita Podcast, Aaron Schwartz sits down with Max Wallace (Senior Director of Customer Experience at Tommy John) and Jamie Smith (Account Executive at Rivo) to unpack a side of ecommerce most brands say they care about but rarely prioritize… retention.

Max has spent over a decade building CX at Tommy John, helping scale the brand from early startup days to a category leader. Jamie has lived every side of the ecosystem, from brand builder to retention tech operator. Together, they share a candid, operator-level view on what it really takes to create experiences customers come back for and tell their friends about.

They dive into:

• Why “everyone focuses on acquisition, but no one focuses on retention”

• How great customer experience quietly becomes your most powerful (and free) acquisition channel

• The reality of CX at scale: a small in-house team, a trusted BPO, and staying obsessively close to the front lines

• Turning a “mountain of feedback” into actual product, policy, and experience improvements

• Why empowering support teams (not scripting them) leads to better outcomes and higher retention

• The fine line between policy and empathy and why “don’t split hairs” is often the right call

• Loyalty programs: why they fail, when they actually make sense, and what’s changed

• The smartest referral strategy most brands aren’t using: turning customers into affiliates

• Building a modern retention stack: loyalty, referrals, accounts, and personalization working together

• AI in practice: from speeding up product development to making sense of overwhelming customer data

• The shift toward segmentation and truly individualized customer journeys (because there is no “average customer”)

From CX philosophy and team design to loyalty strategy, referrals, and AI, this episode is packed with practical insights for operators trying to build brands that don’t just acquire customers, but keep them.

👥 Meet the guests

Max Wallace, Senior Director of Customer Experience at Tommy John

Jamie Smith, Account Executive at Rivo

🎙️ Hosted by

Aaron Schwartz, Co-Founder & Co-CEO at Orita.ai

🎧 Chapters

[00:00] Meet the Operators Behind CX, Retention, and Brand Growth

[05:33] How Max Helped Scale Tommy John’s Customer Experience for 12 Years

[11:11] Jamie’s Wild Path: Mechanic to Coffee to Fashion to Ecommerce

[16:26] Why Most Brands Get Customer Experience Completely Wrong

[22:03] Retention vs Acquisition: Why Loyalty Programs Usually Fail

[26:21] Cut the Noise: Simplifying Your Brand Strategy to What Actually Works

[27:20] The Referral Flywheel: Turn Customers Into Your Best Growth Channel

[28:41] Inside a Brand Operator’s Brain: How Tech Decisions Actually Get Made

[31:45] The Hidden Profit Killer: Returns Fraud and What to Do About It

[36:20] Building a Brand That Lasts 100 Years, not Just the Next Quarter

[38:38] From Data Chaos to Clarity: Making CX Insights Actually Actionable

[40:28] AI Is Rewriting Ecommerce (Faster Than Most Brands Realize)

[43:55] Final Takeaways: Retention, Empathy, and Playing the Long Game

🌐 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.

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