Retail Roundup: AI, Leadership & Retail Media

Welcome to the Retail Roundup. Your weekly brief to help retail leaders decode the biggest news in retail, AI, and commerce—and understand what those developments mean in practice. To kick us off, VP of Editorial & Insights Jeremy Goldman, CEO Marie Chevrier Schwartz, and Senior Retail Analyst Lavina Suthenthiran break down a massive structural shift: the transition from tech experimentation to real-world deployment, the growing value of digitally native leadership, and why smaller brands must abandon corporate copycat strategies to survive. Inside This Week’s Episode: AI: From Experimentation to Practical Deployment - Retail AI has moved past superficial pilots into live, shopper-facing tools focused on solving real customer friction: buying certainty, listing friction, and automated cart building. - While brands are rushing to adopt AI, few have restructured their operations around it. Adoption is currently outpacing true business transformation. "More than 75% of companies are now using AI in their business functions, but only 21% actually redesigned their workflows around it, and only 16% have scaled it enterprise-wide." - Lavina Suthenthiran Rise of the Digitally Native Leadership - The traditional pipeline to top executive leadership is being disrupted. - Boards are now selecting leaders based on digital ecosystem thinking, media literacy, and community building. - Modern fields like retail media are so new that universities don't yet teach them. Retailers have to train their own future leaders internally. “While merchandising and store operations experience still matters, you know, I would say that we have to be really focused on where commerce is headed.” - Marie Chevrier Schwartz How Smaller Retailers Fight Back - Walmart’s multi-billion-dollar acquisitions of Vizio and Vibe.co show how retail giants are linking TV viewing data directly to what customers buy. - Smaller retailers must focus on hyper-specialized product categories, authentic storytelling from real experts, and building passion-driven communities. "Whatever you see Amazon and Walmart doing, you don't try to do the same thing because you're not going to be successful. You have to find other ways to kind of compete in a David and Goliath-like manner." — Jeremy Goldman Click play above for the full conversation on the trends shaping retail.