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When OpenAI announced its Instant Checkout feature last fall, retailers sprang into action.

Etsy, Walmart and Shopify quickly lined up to let users buy merchants' products directly within its ChatGPT chatbot. Suddenly, the e-commerce world was fixated on shopping agents, the artificial intelligence tools that can make purchases on behalf of users.

Shopify President Harley Finkelstein called it the "new frontier" for online retail.

Several months later, OpenAI and its retail partners have headed back to the drawing board.

The AI startup is moving away from Instant Checkout and is now working with retailers to create dedicated apps within ChatGPT. This approach will reroute users to the retailer's own website to complete a purchase, giving those companies more control of the customer experience and the transaction process.

"OpenAI underestimated how difficult the enablement of transactions was going to be, which, on the one hand, is a little surprising, but on the other hand, it's not easy for retailers," Bob Hetu, an analyst at Gartner, told CNBC in an interview.

An OpenAI spokesperson said it is prioritizing better search and product discovery in the chatbot, two areas where it has seen some early traction in user adoption.

"Instant Checkout is moving to Apps, where purchases can happen more seamlessly," an OpenAI spokesperson said in a statement.

The Information was first to report OpenAI's pivot.

The change in strategy has raised questions about whether tech companies and their retail partners oversold shopping bots' readiness. It also highlights the challenges AI startups can face as they attempt to alter the e-commerce landscape that's dominated by incumbent giants like Amazon.

OpenAI, while racing to keep pace with rivals like Google and Anthropic, released a flurry of new offerings and experiences last year in an effort to expand its market share and build out new revenue streams. As shoppers have turned to ChatGPT to ask questions about products, e-commerce emerged as a potentially lucrative opportunity.

While OpenAI tries to figure out its commerce strategy, competitors like Google aren't sitting still.

On Thursday, Google released new updates to its shopping agent platform that enable its systems to load real-time product data, preventing mishaps like out-of-stocks and pricing errors. It also lets users add multiple items to their carts and connect loyalty memberships— two features OpenAI hasn't yet fully cracked.

Agentic stumbles

OpenAI initially billed Instant Checkout as the "next step in agentic commerce, where ChatGPT doesn't just help you find what to buy, it also helps you buy it."

The company said it would collect "a small fee" on each transaction, but declined to disclose any additional financial details.

OpenAI said at the time of the announcement that products from U.S. Etsy sellers would be available to buy directly in ChatGPT, and it expected to add items from "over a million" Shopify merchants at some point.

Onboarding merchants turned out to be an arduous process, and Instant Checkout was prone to errors, said Emily Pfeiffer, principal analyst at Forrester. As of last month, she said, roughly 30 Shopify merchants were available via Instant Checkout.

Walmart made about 200,000 products available for purchase inside ChatGPT, the company confirmed. It's unclear how many Etsy products made it onto the service.

OpenAI could scrape some retailers' websites to obtain data on products surfaced in ChatGPT, but that meant information about whether items were still in stock, estimated delivery timing, or shipping costs could be inaccurate or out of date, Pfeiffer said in an interview.

"Crawling and scraping is inadequate to get the full breadth of product data that you need to do a good job of commerce," Pfeiffer said.

"I think that it was not an ideal shopping experience, but it's not like the death of agentic commerce," she added.

'Adoption takes time'

OpenAI introduced Apps SDK at its annual developer conference in October, and began adding dedicated retail apps to the chatbot from Instacart, Target and several online travel agencies last year.

Shopify confirmed that a new e-commerce experience is coming to ChatGPT.

Buyers will still be able to discover Shopify merchants' products within the chatbot, but the checkout will no longer be native there. Instead, purchases will be completed through merchants' own online stores, either within an in-app browser in the ChatGPT mobile app or in a separate browser tab on the web, the company said.

Merchants will not need to build apps for ChatGPT to participate in that experience.

At an investor conference earlier this month, one of Walmart's top AI executives telegraphed that OpenAI's commerce strategy is in flux. He referred to Instant Checkout as "a very temporary moment in time."

"By this time next month, you will not see that experience anymore," Daniel Danker, Walmart's executive vice president of AI acceleration, product and design, said at Morgan Stanley's Tech, Media & Telecom conference on March 4. "What you will see is that the Sparky experience will travel directly into ChatGPT and Gemini and anybody else that we ever integrate with."

A Walmart spokesperson confirmed to CNBC that the company plans to integrate its Sparky AI assistant in ChatGPT as soon as next week.

An Etsy spokesperson also confirmed that the online marketplace is developing a ChatGPT app. They noted that the timing and direction remains fluid, so an application may not be the end state for how Etsy products appear in the chatbot.

The spokesperson said an app will give it more control over the look and feel of shopping in ChatGPT. It also provides retailers and marketplaces with more shopper data earlier in the purchase journey vs. Instant Checkout, which only gave a view into the transaction after someone made a purchase, they said.

Pfeiffer said the current ChatGPT app experience "leaves a lot to be desired" and there's no guarantee that it will be a successful model for AI shopping.

"Right now, I don't see success in retail apps in ChatGPT," Pfeiffer said. "That doesn't mean there won't be. Adoption takes time."

Early data has indicated that while shoppers are increasingly turning to AI chatbots for product research and recommendations, they're not completing their purchase in the chat window.

Adobe-owned Semrush found that just 22% of users have bought a product inside an AI tool, based on a survey of more than 1,000 U.S. consumers released earlier this month. Half of respondents said they've made a purchase after using AI during research.

Walmart said it found that conversion rates, or the percentage of users who make a purchase, were three times lower for products sold directly in ChatGPT than those that rerouted users to a retailer's website for checkout. Wired first reported the Walmart data.

Etsy observed that ChatGPT has become a valuable discovery channel for online shoppers, though purchase volume from Instant Checkout was relatively low because the technology is still nascent, the spokesperson said.

Retailers who are seeing traffic from chatbots or believe their product is the right fit for that type of experience will likely invest in the platform if they can afford to, Pfeiffer said.

For Etsy, a ChatGPT app could incentivize more sellers to join the platform because it allows them to show up in a new marketing channel, she added.

Amazon, the elephant in the room

Bank of America Securities analysts said in a recent research note that OpenAI's new app-based approach "could enable more partners, such as Amazon," since it allows retailers to more closely manage the user experience and payments in ChatGPT.

Amazon has deepened its ties to OpenAI in recent weeks.

The companies unveiled a strategic partnership last month alongside Amazon investing up to $50 billion in OpenAI. As part of the agreement, OpenAI will make its AI models available to Amazon engineers to develop consumer products.

The companies didn't specify which products may be involved.

At the same time, Amazon has also walled itself off from AI shopping partnerships. The company has blocked dozens of agents from accessing its site, including OpenAI's ChatGPT.

Amazon sued Perplexity in November to try and prevent the startup's Comet browser from scraping and making purchases for users on its website. The legal battle has already been messy.

Perplexity called Amazon's lawsuit a "bald attempt" to block shoppers from using Comet because AI agents "don't have eyeballs to see the pervasive advertising Amazon bombards its users with and cannot be upsold to buy more products."

Amazon continues to invest in its own tools, like its Rufus shopping chatbot and "Buy for Me" agent. The company has also expanded its "Shop Direct" feature, which lets consumers browse and shop products that aren't sold on its site.

As OpenAI works to refine its approach to e-commerce, Hetu said consumers shouldn't count the company out, even as it faces stiff competition.

Pfeiffer added that AI shopping, as a whole, is still early days.

"Everyone thinks everyone else has this figured out, or is farther ahead of them," Pfeiffer said. "The fact is that no one has this figured out."

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