OpenAI’s ChatGPT Checkout Is Live. What Next for D2C Brands?

Summary: OpenAI has launched Instant Checkout inside ChatGPT, starting with Etsy and soon more than a million Shopify merchants including Glossier and Skims. The move collapses discovery and purchase into a single AI-powered surface. It's a shift that could reshape online retail, brand visibility, and conversion economics.

OpenAI has turned what had been the world’s most popular AI chatbot into a checkout. The company’s new Instant Checkout function allows ChatGPT users in the US to buy products directly inside a chat window.

‍At launch the service works with Etsy’s marketplace; “over a million” Shopify merchants, among them Glossier, Skims, Spanx and Vuori, are expected to follow. The payment rails come from Stripe’s Agentic Commerce Protocol, which OpenAI says it will open-source to accelerate uptake. Etsy's chief product and technology officer, Rafe Colburn, said that AI-powered and agentic shopping presents meaningful opportunities for the online marketplace.

The move collapsed the distance between discovery and conversion.

A consumer who once asked ChatGPT for “the best cropped cashmere cardigan under $200” will no longer be bounced out to a brand’s website. Instead, a purchase can be completed in-chat.

OpenAI insists the feature is free to consumers and that “Instant Checkout items are not preferred in results”; but when several merchants offer the same product, whether a seller has enabled the new checkout will influence rankings alongside price, availability and quality. For brands, the implication is plain: switch it on or risk lower visibility.

Markets registered the shift. According to Barron's, Etsy shares rose roughly 7 per cent; Shopify climbed about 4-5 per cent after the announcement, a quick indication of investor belief that conversational commerce could translate into volume.

The e-commerce funnel that once began on Google or Instagram now often begins with a question to an AI model: Which white shirt works under a navy blazer and is in stock in my size?

Vogue Business has described this as the moment AI search becomes “the front door to shopping”, pushing brands to think less about search-engine optimisation and more about AIO — AI optimisation: the data hygiene, trust signals and product narratives that allow large-language models to recommend them in the first place.

That shift aligns with what we argued in February in our feature “How AI Could Solve the $18 Billion Cart Abandonment Problem”. Then we suggested that keyword-era web-shops, with their filters and drop-downs, no longer match how people actually browse. They invite paralysis, not purchase. We posited that a conversational, intent-driven interface could smooth that friction and reclaim abandoned baskets. Instant Checkout operationalises that thesis: the conversation now closes the sale.

Consumer appetite has been primed. A recent Cognizant–Oxford Economics survey found that 22% of consumers use AI to save time. They say, "AI-friendly consumers will drive up to 55% of purchasing by 2030. Convenience, not price, is the killer feature."

Rivals are racing to similar terrain. Google has added “AI Mode” shopping to Search in the US, with virtual try-on, personalised recommendations and agent-led price-match tracking. Apple is reported to be readying its own AI-driven shopping layer inside Safari and Siri. TikTok Shop continues to compress the path from influence to purchase. OpenAI’s step brings its 200-million-plus monthly users into the same field, but with checkout native to the conversation.

For brands the trade-off is less about whether to pay OpenAI’s (undisclosed) commission than whether to risk becoming invisible at the point of decision.

The near-term hit to margin can be offset if frictionless in-chat sales raise conversion enough to compensate for the take-rate. The greater danger is failing to structure catalogues: titles, fabrics, sizing, care data, sustainability proofs, in ways machines can parse and cite. And so slipping out of view when the algorithm chooses among near-identical products.

Luxury labels have particular calibration to make. The likes of Ralph Lauren and Moncler have already invested in AI-powered storytelling, virtual stylists, richer video experiences, to keep their own sites as destinations. For them, agentic checkout is about letting AI handle the repeat purchase while the brand site remains a theatre of narrative and service. Mass-market players, by contrast, will want their full catalogue optimised for agentic pick-lists, bundling basics and subscriptions to capture replenishment.

What comes next will matter: multi-item carts, expected soon, could raise average order values dramatically. Open-sourcing the protocol may draw in Adobe Commerce or BigCommerce, broadening the pool of eligible merchants. Regulators may press OpenAI on how ranking signals intersect with checkout enablement. And platform-level competition, especially from Google and Apple, will test whether a single AI surface can dominate shopping any more than search once did.

Those that brands that wait risk paying not just an “AI tax”, but the cost of being unseen. Treat ChatGPT as a new sales channel, optimise product data for AI discovery, and shift part of your performance budget to test and measure in-chat conversion.