Retail media is growing fast, but the real work is happening underneath the surface — in the systems, workflows, and relationships that make it all run.
In this episode of The Middlemen Podcast, Tom Limongello and Scott Messer sit down with Drew Cashmore, Chief Strategy Officer at Vantage and one of the early builders of Walmart Connect, to break down what “orchestration” actually means inside a modern retailer.
Most people talk about retail media in terms of new ad products, paid search expansion, or offsite performance. But Drew argues that retail media really runs on two parallel tracks:
All the infrastructure that connects channels, normalizes reporting, syncs product feeds, passes audience data, and makes ads actually serve.
Where brands, merchants, marketers, and retail media teams align on goals, budgets, JBPs, promotions, category growth, and in-store activation. This is where orchestration lives — and where most retailers are still struggling.
Drew brings a rare, practical perspective from his work at Walmart Connect, Firework, and now Vantage, where he’s helping retailers build the connective tissue between trade, retail media, and merchandising.
Orchestration is becoming the operating system for retail media. Retailers who get it right will integrate trade, media, and merchandising into a unified strategy. Retailers who don’t will continue to lose ground to Amazon — not because of ad tech, but because of alignment.
Drew Cashmore — “Retail Media Leapfrog Series: Eating Trade?”
We're here to explain the most confusing topics in retail media, ad tech, mar tech and e-Commerce.
