Retail & Retail Media Strategist Writer Keynote Speaker

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.

Drew Cashmore moderating a panel with Walmart Connect
Drew Cashmore
Who I am

Two decades inside retail and retail media — helping leaders build what comes next.

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.

Vantage · Walmart · Walmart Connect · Bain & Company Executive Advisor · Media in Retail
01 · Writing

Retail Leapfrog Series

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.

02 · Speaking

Public and corporate keynotes.

Keynotes and workshops for retailers, brands, and the platforms in between. Three catered talks in 2026 or custom on demand.

Drew Cashmore speaking at IAB Europe
IAB Europe · Keynote
Drew Cashmore at The Lead Conference
The Lead · Fireside
Keynote
Passing the Great Stall.
Rest-of-market retail media is stalling while Amazon and Walmart pull away. Drawing on the Leapfrog Series, this keynote lays out the growth levers that actually move the needle next — investing to break the stall, unifying the buy, owning the advertiser relationship, and competing on outcomes — for the North American market.
North America
Internal Workshop
Renovating the Half-Built House.
Retail media's organizational debt — the deferred foundations, manual workflows, and one-way-door decisions that quietly become the operating model. The optimistic part: the house is debt you chose, so you can choose to finish it — and it doesn't take being a giant, just deciding early and on purpose.
North America
Keynote
What Europe can teach the world about retail media.
Europe built retail media for the shopper and operationalized the hardest part first — in-store. A keynote on the four philosophies the rest of the world keeps overlooking, and why the customer-centric playbook is the real competitive moat.
Europe
Selected · 2022 — 2026

Recently on stage.

2026
IAB Leadership Breakfast
AI's Impact on Commerce and Retail Media
Cannes
2026
P2Pi Retail Media Summit 2026
The third great advertising business — a keynote.
Chicago
2026
Toronto Tech Week AI in Retail Summit
AI in retail and retail media
Toronto
2026
Corporate Keynote (Retailer)
What Europe can teach the world about retail media
Boston
2025
Ascendant Network European Summit
Trade vs. retail media
London
2025
Corporate Keynote (Retailer)
The new operating model in retail
Cincinatti
2025
IAB Europe Retail Media Summit
What Europe can teach the world about retail media
Amsterdam
2025
Corporate Workshop (Brand)
Rethinking relationships with retailers.
Vevey
03 · About

Two decades inside the work.

Drew Cashmore portrait

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.

Now
Chief Strategy Officer, Vantage.
Previously
Walmart Connect, Walmart Global eCommerce, Firework
Writes
The Retail Leapfrog Series — on the new operating model for retail.
Boards
Media in Retail Board Chair (RETHINK Retail), Fluent Advisory Board
04 · Newsletter

Retail Leapfrog Series

Essays on retail media and the new retail operating model, podcasts, and the occasional unfinished thought.