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Why Retail Media Is Entering Its Most Transformative Phase

📍New York, USA

Retail Media has become one of the fastest growing engines of profitability and transformation in retail. Yet long before the industry understood its potential, Sherry Smith was already shaping its foundations. In this episode of OFFBounds, Sherry, now President of Retail Media at Criteo, takes us back to 2008, when retail media was still undefined and digital activation was experimental. She reflects on an era when companies like Walmart were just beginning to explore digital monetization and when measurement, talent, and structures looked nothing like they do today.

The turning point came in 2020. What was once a gradual rise quickly accelerated as retailers rushed to prioritize ecommerce, strengthen data strategies, and prove measurable value. Sherry describes that period as a crash course for the industry. Retail Media Networks multiplied, talent shifted dramatically, and retailers learned to operate more like publishers. Brands, on the other hand, had to evolve beyond viewing retail media as only bottom-funnel conversion, expanding into awareness, consideration, and omnichannel planning.

Looking ahead, Sherry highlights two transformative shifts. The first is the move to self-serve activation. For years, retailers operated with managed service models that limited transparency and slowed execution. Now, brands want direct control, real-time measurement, and unified planning across media formats. The second shift is the integration of AI and conversational shopping. As shoppers move toward agent-assisted discovery, merchandising, media, and experience will no longer operate in separate tracks. Teams, systems, and investment models must fully connect around the customer journey.

Sherry leaves listeners with candid advice. To prepare for the next 18 months, companies must hire differently, organize teams around shared outcomes, reduce operational fragmentation, and learn quickly. Curiosity, adaptability, and transparency will separate those who lead from those who follow. This conversation is not only a history lesson, it is a view into where retail media is heading and why this next chapter will redefine how brands grow, how retailers operate, and how customers shop.

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