Retail is being rewritten by many forces at once. I help inspire retail leadership teams adopt new operating models and rethink what it is to be a retailer in 2026.
I'm a retail and retail media strategist, Chief Strategy Officer at Vantage, and former retail executive at Walmart and Walmart Connect. My work is about the new operating model for retail — how retail media, AI, and a changing customer are converging into a different way of running the business, and how leadership teams turn that shift into strategy they can actually execute.
Why rebuild what's already been proven? The Retail Leapfrog Series captures how leading retailers built their advantage, so others can leapfrog the incumbents instead of starting over. Retail media first — more of retail to follow.
Keynotes and workshops for retailers, brands, and the platforms in between. Three catered talks in 2026 or custom on demand.
Drew Cashmore is a retail and retail media strategist with two decades inside the category — in internal operating roles, and beside the retailers and brands working out what comes next. He is currently Chief Strategy Officer at Vantage — a technology platform connecting the disparate pieces of retail media and retail marketing into a unified operating system — and was formerly part of the executive team that built Walmart Connect.
His work is about the new operating model for retail — how retail media, AI, and a changing customer are converging into a different way of running the business, and how leadership teams turn that shift into strategy, org design, and change they can actually execute.
He writes The Retail Leapfrog Series, speaks on stages from NRF to IAB Europe, and advises retailers and brands navigating the transition. The writing is where the thinking gets tested; the talks are where it travels.