DoubleDash, Designer Shoes, and a Door to Retail Media: DoorDash’s Big Reveal with Toby Espinosa

Christine Russo, host of What Just Happened, sits down with Toby Espinosa, Vice President of DoorDash Ads, to discuss the company’s evolution and its growing role in retail media. Espinosa, who has been with DoorDash for a decade, shares how the company expanded from a local restaurant delivery startup into a global, multi-category logistics platform serving 30 countries. Initially created to help small businesses grow through delivery logistics, DoorDash has since launched promotions, advertising tools, and partnerships to support both local entrepreneurs and large brands alike.Espinosa highlights DoorDash’s commitment to simplifying complex challenges for small businesses. Recognizing that local business owners often wear many hats, DoorDash developed a CPA-based ad model that removes financial risk from merchants by only charging when an ad converts to a sale. This model has driven significant adoption and trust from local operators while improving ad relevance for consumers. Espinosa emphasizes that the company’s strategy is simple—deliver any product to any consumer within 30 minutes or the same day—but executing it and reducing complexity for partners remains a key challenge.The conversation also covers three major announcements: the launch of DoubleDash Ads, a new ad placement that drives incremental sales during the checkout experience; a strategic partnership with TopSort to extend ad reach beyond the DoorDash platform; and DoorDash’s entry into the fashion category through its partnership with Designer Shoe Warehouse. Espinosa explains that the broader vision is to unlock local inventory, enabling consumers to access hundreds of thousands of SKUs already available in their neighborhoods. Russo closes by praising DoorDash’s thoughtful strategy and consumer-first mindset in tackling the future of last-mile logistics.