Watson Weekend hosts Rick Watson and Jessica Lesesky cover the latest retail industry news and trends this week. The headline hangover includes Gen Z's influencer-driven purchases, Mastercard's entry into retail media advertising, potential U.S. government influence over ‪@tiktok‬'s algorithm, and @Stripe's AI-powered commerce platform.

Guest Kiri Masters, a retail media analyst and Founder of ‪@retailmediabreakfastclub‬, discusses the complexities of retail media networks, internal conflicts within retailers and brands, and the evolving role of AI and large language models in retail advertising and shopping.

They explore challenges in aligning retailer and brand goals, the impact of agentic commerce on retail media, and the importance of customer loyalty and differentiation beyond price competition.

The conversation highlights the potential for AI to transform retail media, creative, and customer experiences, while acknowledging current limitations and organizational hurdles.

The Watson Weekend is sponsored by Mirakl — Because “Traditional eCommerce” Is Just Code for “Not Growing.” Join 450+ retailers scaling 6X faster with AI, automation, and enterprise-grade marketplaces, dropship, and retail media. It’s time to accelerate with Mirakl.

Chapters:

Welcome to The Watson Weekend - 0:00

Headline Hangover 03:08

Introducing Kiri Masters 18:07

Internal conflicts within retailers and brands 23:11

The push-pull dynamics internally between teams 26:22

Organizational challenges inside retailers 32:22

Off-site media and retailers not sharing data 35:55

Agentic Commerce 38:29

Microsoft and contextual ads inside Co-Pilot 48:41

The impact of large language models on advertising 55:50

The perfect price conundrum 01:01:15

Loyalty in an agentic world 01:05:22

The dark side of creative 01:11:24

The end of the show 01:12:59

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