[Editor’s Note: Agents of Transformation is an independent GeekWire series and March 24, 2026 event, underwritten by Accenture, exploring the people, companies, and ideas behind AI agents.]
Microsoft is making its own bid to turn AI conversations into agentic commerce, announcing a new feature called Copilot Checkout that lets users complete purchases directly within its AI chatbot, without being redirected to an external website.
The company is betting that its existing enterprise technology footprint and established relationships with large retailers will give it an edge over OpenAI, Google, and Amazon in winning over merchants wary of giving up control to retail rivals or AI intermediaries.
“We’ve designed it in such a way that retailers own those relationships with the customers,” said Kathleen Mitford, corporate vice president of global industry marketing at Microsoft. “It is their data, it is their relationship, and that’s something that’s really important to us.”
It’s part of a broader AI rollout by Microsoft at NRF 2026, the retail industry’s annual conference in New York. Microsoft is also launching Brand Agents, pitched as a complete solution for Shopify merchants to add AI assistants to their websites, along with new AI tools to assist store employees and help retailers enhance their online product listings and metadata.
Copilot Checkout works by surfacing products from partner retailers within Copilot search results. Purchases can be completed without leaving the conversation. Microsoft says the retailer remains the merchant of record, handling fulfillment and customer service.
But will people buy in chat?
The bigger question for the tech industry is whether chat-based commerce is actually the next big thing. Forrester analyst Sucharita Kodali, for example, previously told GeekWire that “e-commerce isn’t a problem that needs to be fixed.” She added that it’s unclear what value chat-based commerce is bringing to retailers, “other than disintermediating Google.”
Microsoft’s Mitford offered a different take in an interview this week, saying that consumer behavior is shifting faster than it may seem. She drew a parallel to how quickly businesses moved from experimenting with AI to putting it into operation over the past year.
“I see the same thing happening with consumers … it just takes a little bit of time,” Mitford said, predicting that the speed of consumer adoption will eventually match the rapid uptake seen in the business world.
Copilot Checkout is rolling out now in the U.S. on Copilot.com, with PayPal, Shopify, and Stripe handling payment processing. Etsy sellers will be among the first available on the platform. Shopify merchants are set to be automatically enrolled following an opt-out window.
That last detail is notable given the backlash Amazon has faced over its “Buy for Me” feature, where brands complained about being included without consent and seeing inaccurate listings.
Microsoft’s approach is more tightly connected to its partners — the company said Shopify will management the opt-out process for its merchants — but automatic enrollment seems to raise the potential for some of the same concerns. (We’ve contacted Shopify for more information.)
The competitive landscape
More broadly, Microsoft is playing catch-up on the consumer side.
OpenAI launched Instant Checkout in ChatGPT last September, partnering with Shopify and Stripe to let users buy from more than a million merchants. Google followed in November with its own “Buy for Me” feature which lets its Gemini assistant purchase products on a user’s behalf.
Despite its inroads with businesses, Copilot has a fraction of ChatGPT’s market share with consumers. Recent data from Similarweb’s Global AI Tracker showed ChatGPT with about 68% of AI chatbot web traffic, with Google Gemini at 18% and Copilot in the single digits.
But Microsoft has its advantages: Unlike Amazon and Google, which compete directly with retailers through their own marketplaces, it isn’t a retailer. And retail has long been a major vertical for its enterprise cloud and software business, with large chains running on Azure and Microsoft 365.
Mitford said Microsoft is leaning on its existing trust and long-standing relationships with retailers, along with a commitment to responsible AI, to help differentiate itself from rivals.
Microsoft is making the broader case for AI to retailers based on return on investment. A Microsoft-commissioned study from IDC, released in November, found that retail and consumer packaged goods companies are seeing a 2.7x return on every dollar spent on generative AI.
Mitford, a former fashion designer who has been in the technology industry for most of her career, said she sees the retail sector among the leaders in AI uptake across the business world.
The technology, she said, is being “adopted at a pace that I’ve never seen.”
