The craze around AI in retail is real. And anyone looking for clear answers on how to execute an AI playbook needs to realize that agent-assisted shopping will take time to catch on. Take OpenAI’s instant checkout feature, which didn’t land, primarily because people weren’t ready for it. However, it wasn’t necessarily a failure. OpenAI launched its Instant Checkout with a handful of merchants on Etsy and Shopify in September 2025, and then rolled it back, letting retailers handle their own checkout, in March. “We’ve found that the initial version of Instant Checkout did not offer the level of flexibility that we aspire to provide, so we’re allowing merchants to use their own checkout experiences while we focus our efforts on product discovery,” OpenAI said in a blog post. During Retail Brew’s recent virtual event, Andy Szanger, director of strategy at CDW, said the issue wasn’t that the OpenAI checkout feature was broken or unsuccessful; it had more to do with the timing of the rollout. “It is really more of a failure of sequence, and more precisely, a failure to understand the difference between what technology can do and what consumers are ready for it to do,” Szanger said. Keep reading here.—VC |