In today’s episode, I dive into one of my favorite topics—those unexpected career-defining moments that shape everything. I’m talking about the “sliding doors” decisions that, in hindsight, changed the trajectory of some of the most impressive retail media leaders I know. You’ll hear real, raw stories from brand-side professionals who took chances, followed curiosities, or simply annoyed the right person at the right time—and it paid off.

From mentorship programs that reshaped mindsets to the grind of early Amazon days, and serendipitous job ads in local papers, this episode is packed with career pivot moments that will inspire you to lean into your own opportunities—even the ones that don’t look glamorous at first. Whether you’re new to eCommerce or a seasoned pro, these stories are a reminder that the path to success in retail media is rarely a straight line.

⏱️ Timeline Summary

[1:28] - Julie Liu shares how mentorship with Sarah Hofstetter led her to rethink her career through a new lens of soft skill development.

[3:30] - Josh Clarkson reveals how being persistently curious helped him land a role on the Amazon team—kickstarting his eCommerce journey.

[4:59] - Todd Wegen recalls a bold leap from a dull project management role into a startup that pioneered eCom tools—and eventually Amazon.

[7:00] - Jace Ree tells the story of how a chance conversation led him from shopper marketing into an Amazon Fresh role that changed everything.

[9:33] - Reflections on the evolution of eCommerce and how early adopters paved the way for today’s specialized talent pool.

🔗 Links & Resources
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Today I’m digging into the latest insights from Pentaleap’s biannual Sponsored Products Benchmark Report—and it’s challenging some long-held assumptions about online advertising. Shoppers say they don’t love ads, but the data tells a different story. I’m sharing what Amazon, Walmart, and Home Depot are doing right when it comes to high-volume sponsored product listings—and what mid-tier retailers can learn as they scale their retail media networks.

We explore the delicate balance between ad inventory expansion and shopper satisfaction, and I highlight how smart retailers are mastering ad relevance to avoid click fatigue. I also break down why increasing sponsored product coverage doesn’t have to mean compromising user experience—and how it can actually unlock significant revenue potential if done right. Whether you’re building your retail media strategy or refining an existing one, this episode is packed with practical takeaways.

🕒 Episode Timeline

[0:36] - The surprising truth: heavy ad coverage doesn’t always hurt engagement

[1:22] - Market leaders vs. mid-tier retailers: who’s winning at retail media

[2:26] - Kroger’s leap in ad coverage and why it matters

[3:18] - Why under-monetized search inventory is still a missed opportunity

[4:24] - How Amazon keeps CTR high even with more ads

[5:25] - Grid strategies: how Walmart, Staples, and CVS handle ad placement

[6:39] - The risk of irrelevant ads—and how they can hurt both sales and trust

[7:35] - A simple framework to decide how many ads are too many

[8:00] - Key takeaways for maximizing retail media without annoying your shoppers

🔗 Links
Pentaleap's 1H25 Sponsored Product Benchmark report
Read the original post for this episode in my Forbes column
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In today’s episode, I unpack why so many shoppers are brushing off AI chatbots and recommendation engines—even as they quietly benefit from other AI-powered features during their online shopping journeys. Drawing insights from a fresh Akeneo survey of U.S. consumers, I highlight the trust gap that exists when it comes to visible AI tech like chatbots versus the more invisible enhancements like AI-generated review summaries.

We’ll explore how consumer behavior contradicts what they say in surveys, why retailers might be misplacing their AI bets, and what types of AI integration actually do enhance the customer experience. This one’s a reality check for anyone building out retail AI strategies—and a bit of a defense for the oft-maligned chatbot (well… kinda).

Chapters

[00:00] – Reflecting on yesterday’s AI chatbot critique

[00:46] – New survey reveals big gap: 75% encounter AI, but only 44% engage

[01:33] – Why consumers claim they don’t trust AI shopping tools

[02:18] – The problem with self-reported surveys in understanding tech behavior

[02:40] – Amazon’s quiet success with AI-generated review highlights

[03:52] – Consumers unknowingly love certain AI features—but hate the label

[04:32] – The paradox: people trust ChatGPT, but not your retail chatbot

[05:19] – Where retailers should (and shouldn’t) use AI in customer experiences

[05:36] – Invitation to join the upcoming “Retail Media Halo Effect” webinar

Register for the Future Commerce webinar, "The Retail Media Halo Effect," on Wednesday (May 21, 2PM ET)
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