How retail executives will be evaluating ChatGPT checkout this holiday season

One C-suite executive at another large specialty retailer told Modern Retail on the condition of anonymity that their company is investigating ChatGPT’s Instant Checkout but doesn’t consider it “ready for prime time.” They said that, for it to get there, it would need features such as real-time inventory tracking, coupons, promotions, customer data collection, integration to the retailer’s loyalty program and store pickup integration.

In short, while many in the industry will be watching ChatGPT checkout closely this holiday season, they are skeptical of how quickly it will shape into an effective sales driver and offer the technology capabilities retailers and brands expect out of a shopping platform.

“The topic is hot with my peers at other retailers,” said a tech executive at another major specialty retailer. “Many are bullish but don’t believe the benefit will be there for this holiday season.” That executive said they believe this holiday season will be a testing ground for a few big retailers that could lead to wider adoption next year.

An OpenAI spokesperson declined to share how many merchants it plans to bring onto the platform by the end of the year, but said it hopes to scale to many more merchants through the Agentic Commerce Protocol, an open standard codeveloped by OpenAI and Stripe allowing orders to flow from ChatGPT into retailers’ e-commerce systems.

Through the Agentic Commerce Protocol, merchants can start building their own integrations and can then apply to have their products made available for purchase through ChatGPT. Purchases are powered by Stripe, and merchants pay a small fee on each order, while there is no charge to users. The exact cost of the merchant fee is unclear.

The program began earlier this month with Etsy sellers and will later expand to Shopify sellers. On Oct. 14, Walmart announced its partnership with OpenAI bringing its product catalog to ChatGPT, while also building out its own Sparky chatbot.

“For many years now, e-commerce shopping experiences have consisted of a search bar and a long list of item responses. That is about to change,” Doug McMillon, president and CEO of Walmart, said in a news release. “There is a native AI experience coming that is multimedia, personalized and contextual.”

Potential benefits, drawbacks for retailers, brands

It is yet to be seen whether Instant Checkout will be a major revenue driver for retailers and brands.

“Everybody’s very concerned about the future of agentic commerce and see it as a potentially big disruptive thing; this first implementation from ChatGPT probably doesn’t consume a huge chunk of consumer behaviors,” said Jason Goldberg, chief commerce strategy officer for Publicis Groupe.

Goldberg said that, because Instant Checkout is currently limited to single-item purchases, it wouldn’t make sense for a large swath of retailers who sell 60-item grocery carts or three-item apparel outfits, for example.

“Everyone assumes, over time, it will expand and have more of those capabilities,” Goldberg said. “At the moment, people are mostly interested in it as a test-and-learn-type environment.”

Still, Goldberg said ChatGPT’s checkout integration was surprisingly friendlier to retailers than he had expected, feeding directly into retailers’ sales platforms instead of competing with them. He said he had expected it to be a marketplace where OpenAI would be the seller of record.

“They launched an elegant implementation where they’re not the merchant of record … and where the seller gets all the customer data,” Goldberg said. “That makes it much more palatable and interesting for a variety of different sellers and merchants to test being on it.”

In addition to the potential benefits of tapping into ChatGPT’s user base, Gartner director analyst Brad Jashinsky said working with companies such as OpenAI and Perplexity early in their evolution gives retailers a chance to learn about the limitations of the AI platforms as well as their own systems. It could help them determine what their technology needs are for 2026 and beyond.

“Organizing product data and other things like that can take a long time, especially if there’s additional technology needed,” Jashinsky said. “Being able to experiment early supercharges your team’s learning on that side.”

Additionally, for public retail companies, any investment in AI — including Instant Checkout — may be attractive to investors as the technology is currently fueling the stock market. Largely due to the AI boom, the top five companies on the S&P 500, including Nvidia, Microsoft and Apple, now make up nearly 30% of the index, according to CNBC.

Melissa Minkow, global director of retail strategy and insights for CI&T, said her clients are not yet asking about Instant Checkout, as it isn’t yet available to everyone. But they are concerned about preparing for the growth of ChatGPT and other AI platforms.

“The biggest thing I keep hearing from [clients] is, ‘How do we prepare our channels?’ ‘How do we become a destination so that we’re not mutually exclusive?'” Minkow said. “And then, simultaneously, ‘How do we make sure that our channels will get picked up by these queries, so that we’re not missing the boat there?'”

Will people shop in ChatGPT?

The new checkout feature comes as 44% of U.S. consumers in a Gartner survey conducted this year said they would be willing to let AI tools assist with shopping tasks.

This varied significantly by age demographics, with 56% of millennials willing to pass tasks to AI, followed by 48% of Gen Z respondents, 47% of Gen X respondents and 25% of baby boomers. And nearly 60% of U.S. consumers have used a generative AI tool for help with online shopping, according to an August 2025 survey from Omnisend, signaling a large user base of potential shoppers within the platform.

Jashinsky said he and other consultants at Gartner have had to temper some clients’ expectations about the speed at which consumers will adopt these tools. “Even before OpenAI announced these partnerships, … there was already interest and maybe a little bit of fear from some of our retail clients about, ‘How do we prepare for this?’” Jashinsky said. “Anytime we see these types of really big innovations happening, these big shifts, I think sometimes the timeline is a little bit blown out of proportion.”

The speed of AI-shopping adoption, especially in the short term, may vary by sector. Bobby Watts, svp of retail media, digital merchandising and marketing for Ahold Delhaize USA, told Modern Retail at the Groceryshop conference earlier this month that, as of now, Instant Checkout is more ideal for customers who are researching and purchasing a single item — so it’s less likely to be ideal for grocers. That’s because customers are still initiating the purchase on their own within the app.

However, he believes that, eventually, as AI becomes more agentic and can purchase products on customers’ behalf, it will become more relevant to the sector.

“Consumers aren’t going to just go to ChatGPT and say, ‘I need bananas,’ or ‘I need a box of cereal.’ They’re typically buying a basket, or they’re buying a meal, or they’re buying an occasion; it’s not just the one item,” Watts said. “What it’ll probably evolve to is that the consumer will say, ‘I want this basket of groceries,’ ‘I want all of these things,’ ‘Go find me the best value for the basket.’”

Previous attempts to bake checkout features into platforms that people turn to for discovery and product suggestions have had mixed results. Instagram previously tested a checkout tool that let users buy products directly inside its app, only to later discontinue the feature in 2022. Some brands, including handbag brand Dagne Dover and Eyebuydirect, told Modern Retail at the time that Instagram’s shopping features did not make up a significant portion of their overall revenue. However, TikTok Shop has since exploded in popularity, and it more than doubled its revenue from 2024 to 2025.

“If Instagram were to try it again now, I’d be curious if those numbers were significantly higher,” Minkow said, adding that there may have been a lack of trust or the feature may have come out too early in the adoption curve. “My guess would be that they would be higher, because I think consumers have become a lot more tech-comfortable when it comes to leveraging different channels to make purchases. It may have just been too soon for that technology, especially because … there’s a lot of conversion happening via TikTok.”

Adding an advertising network is key

The retail tech executive Modern Retail spoke with on anonymity said the platform isn’t currently accessible to most retailers and that it would need its own advertising network to achieve wide adoption. The adoption of ChatGPT as a shopping platform “could have a significant impact on ad budgets of the future and potential shifts away from Google,” they said. “As always, though, the ad dollars will go where the traffic and conversion exist.”

OpenAI has not yet launched an ad network for ChatGPT, but the company is building out a monetization team to manage how it could generate revenue across the company, an OpenAI spokesperson said. The spokesperson added that, in addition to launching commerce features, OpenAI has already monetized ChatGPT’s advanced features by rolling out plans for business, enterprise and education users, and launching ChatGPT Go, a low-cost plan for users in India and Indonesia. The company also offers paid plans for individual users.

The company has been laying what could be the foundation for an ads business, according to Digiday. In April, internal documents forecasting “free user monetization” — in other words, making money through advertising — were leaked. OpenAI optimistically projected it could bring in $1 billion in 2026 and $25 billion by 2029. In May, the company hired Instacart’s CEO, Fidji Simo, who earlier helped launch advertising on the news feed at Facebook. And this month, the company launched the Sora video generation app and a ChatGPT browser that could display ads.

“If you’re a retailer like Walmart or Amazon — these retailers that have significant retail media revenue — that is a huge risk,” Jashinsky said. “If people are not going to your website, you’re not able to show those retail media and advertising.”