Chad Lusk names Fidji Simo, the former CEO of Instacart, as his pick for Retail CEO of the Year based on her move to OpenAI as the CEO of Applications. Lusk believes this was a "smart move" for Simo individually and views it as a "microcosm for retail commerce more broadly."

Lusk notes that e-commerce used to be the main focus, but AI "will matter tomorrow." Simo's background is strong: she ran the Facebook app at Meta until 2021, led Instacart during the time when "grocery delivery acceleration mattered," and is now "moving to AI when that matters". She is considered a guru for "productizing, scaling, monetizing consumer apps."

Simo's move was also a "big statement for OpenAI itself," showing they were ready to transition from a research and innovation lab into "large-scale AI deployment to create and monetize products and services" in areas including commerce and advertising platforms. Lusk states that the award is not based on what Simo has done in her role at Instacart, but rather on the "big bold risky strategic move for a person who's betting on the direction of the industry and the role that she can play to shape it."