Shop ’til you bot: Google, OpenAI, and the race to build agentic commerce

FastCompany: Last September, OpenAI and Shopify made an announcement that sent ripples throughout the retail industry: They were partnering to launch Instant Checkout—a feature that would let people complete purchases directly within ChatGPT. Within months, the AI giant promised, we would be able to ask ChatGPT for Mother’s Day gift ideas or top-rated lightbulbs, and then click to buy products instantly. Shopify’s president, Harley Finkelstein, declared this the “the new frontier” of retail. But if you’ve tried to shop on ChatGPT recently, you know that this future never arrived. OpenAI quietly killed Instant Checkout in March.

The official story, according to OpenAI’s blog post , was that the checkout feature “did not offer the level of flexibility that we aspire to provide.” The unofficial story is that OpenAI and Shopify were unprepared for the level of complexity checking out requires. Fewer than 30 of Shopify’s millions of merchants ever went live. This is the state of AI shopping in 2026. The same company reportedly being trained to guide drone strikes in active conflict zones cannot build a working check-out.

My interviews with executives at Google, OpenAI, Stripe, Walmart, and a long list of AI-focused startups , revealed that the technology powering AI—large language models—is incompatible with existing e-commerce technology. Behind the scenes, there’s a massive effort underway in the retail industry to build the infrastructure required to make AI shopping possible. The commerce leads at Google and OpenAI, the two biggest players in the space, say that we’re months—not years—away from a tipping point where agentic commerce really will become commonplace.

Whoever makes the shopping experience consumers want to use will own one of the most lucrative pieces of real estate in the history of retail. In this story you’ll learn: The knotty problem that forced OpenAI to pull back on instant checkout How frontier labs are rebuilding commerce infrastructure from the ground up Which company is most likely to win the AI shopping war OpenAI’s false start and new vision Last year, as AI became the fastest-adopted technology in history , AI companies realized they needed to turn their attention to commerce. There’s a lot of money hanging in the balance.

According to McKinsey , AI-driven commerce could generate $1 trillion in U.S. revenue and up to $5 trillion globally by 2030. As we entered 2026, the retail industry’s newest buzzword was “agentic commerce,” which refers to AI agents shopping autonomously on the user’s behalf. “Nobody has figured it out, but everyone has FOMO,” says Emily Pfeiffer, principal analyst at Forrester, who covers AI and commerce. “Everyone is prematurely rushing to market.” Case in point: The botched Instant Checkout roll-out.

When they announced the checkout feature, Shopify and OpenAI had promised that millions of Shopify merchants would soon be shoppable from ChatGPT, alongside Etsy sellers and Walmart. A tiny fraction of the integrations were built. “Shopify has major egg on their face,” says Omar Qari, the CEO of Logicbroker, which helps brands feed product data into LLMs. “If you go back to late last year, OpenAI said, ‘ We’ve solved it.

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The article addresses a significant shift in e-commerce driven by AI, highlighting a major partnership that could redefine shopping experiences, making it highly relevant and impactful for brand strategy professionals.