OpenAI’s Second Act: Re-attempting Agentic Shopping After Initial Setback

OpenAI Pivots E-commerce Strategy: From Instant Checkout to Dedicated Apps

The promise of seamless, AI-driven commerce within chatbots has hit a significant speed bump. OpenAI, the artificial intelligence powerhouse behind ChatGPT, is recalibrating its approach to e-commerce, moving away from its ambitious “Instant Checkout” feature and shifting focus to the development of dedicated retail applications within its flagship chatbot. This strategic pivot underscores the complex challenges of integrating transactional capabilities into conversational AI and highlights the enduring dominance of established e-commerce giants.

When OpenAI first unveiled Instant Checkout last fall, it triggered a wave of enthusiasm and rapid action from major retailers. Companies like Etsy, Walmart, and Shopify quickly embraced the initiative, aiming to enable users to purchase products directly within ChatGPT. This marked a bold step into the burgeoning realm of “shopping agents”—AI tools designed to facilitate purchases on behalf of consumers. Shopify President Harley Finkelstein heralded it as the “new frontier” for online retail.

However, several months into the experiment, it appears that the envisioned frictionless checkout experience has encountered considerable hurdles. OpenAI is now collaborating with retailers to build bespoke apps within ChatGPT. This new paradigm will direct users to the retailer’s own website to finalize transactions, thereby granting businesses greater oversight over the customer journey and payment processes.

“OpenAI underestimated how difficult the enablement of transactions was going to be,” noted Bob Hetu, an analyst at Gartner, a prominent research and advisory firm. “While that’s somewhat surprising, it’s also not a simple task for retailers.”

An OpenAI spokesperson indicated that the company is prioritizing improvements in search and product discovery within ChatGPT, areas that have already shown promising user engagement. “Instant Checkout is moving to Apps, where purchases can happen more seamlessly,” the spokesperson stated, confirming a report by The Information.

This strategic shift has ignited discussions about whether tech companies and their retail partners may have prematurely hyped the capabilities and readiness of AI-powered shopping bots. It also casts a spotlight on the formidable obstacles AI startups face when attempting to disrupt an e-commerce landscape largely controlled by established players like Amazon.

Amidst a race to keep pace with rivals such as Google and Anthropic, OpenAI has been aggressively introducing new offerings and features to expand its market share and diversify revenue streams. As consumers increasingly turn to ChatGPT for product inquiries, the e-commerce sector emerged as a potentially lucrative avenue for the AI company.

While OpenAI navigates its commerce strategy, competitors are not standing still. Google, for instance, recently updated its shopping agent platform, enabling its systems to load real-time product data. This enhancement aims to mitigate issues like stockouts and pricing inaccuracies and allows users to manage multi-item carts and integrate loyalty programs—features that OpenAI has yet to fully master.

Agentic Stumbles in Commerce

OpenAI initially positioned 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 had planned to levy a “small fee” on each transaction, though specific financial details were not disclosed. At the time of its launch, OpenAI announced that products from U.S. Etsy sellers would be available for direct purchase within ChatGPT, with plans to eventually incorporate items from “over a million” Shopify merchants.

However, the onboarding of merchants proved to be a complex and time-consuming process, and the Instant Checkout functionality was reportedly prone to errors. Emily Pfeiffer, a principal analyst at Forrester Research, observed that as of last month, only about 30 Shopify merchants were accessible via Instant Checkout. Walmart confirmed that it made approximately 200,000 products available for purchase within ChatGPT, though the number of Etsy products integrated remains unclear.

Pfeiffer explained that while OpenAI could scrape retailer websites for product data, this method often resulted in outdated or inaccurate information regarding stock availability, delivery timelines, and shipping costs. “Crawling and scraping is inadequate to get the full breadth of product data that you need to do a good job of commerce,” she stated. “I think that it was not an ideal shopping experience, but it’s not like the death of agentic commerce.”

Adoption Takes Time

OpenAI introduced its Apps SDK at its developer conference in October, subsequently integrating dedicated retail applications from partners like Instacart and Target, alongside several online travel agencies. Shopify has confirmed the upcoming introduction of a new e-commerce user experience on ChatGPT. While users will still be able to discover Shopify merchants’ products within the chatbot, the checkout process will no longer be native. Instead, purchases will be completed on the merchants’ own online stores, accessed either through an in-app browser on the ChatGPT mobile app or a separate browser tab on the web. Merchants will not be required to develop distinct apps for ChatGPT to participate in this revamped process.

During an investor conference earlier this month, a senior AI executive at Walmart suggested that OpenAI’s commerce strategy was in flux, referring to Instant Checkout as “a very temporary moment in time.” Daniel Danker, Walmart’s Executive Vice President of AI Acceleration, Product, and Design, stated, “By this time next month, you will not see that experience anymore. What you will see is that the Sparky experience will travel directly into ChatGPT and Gemini and anybody else that we ever integrate with.” Walmart has confirmed plans to integrate its Sparky AI assistant into ChatGPT as early as next week.

An Etsy spokesperson confirmed that the online marketplace is developing a ChatGPT app, acknowledging that the precise timing and direction are still fluid, and an app might not be the final form of Etsy’s presence in the chatbot. The spokesperson emphasized that an app would offer greater control over the shopping experience within ChatGPT and provide retailers with earlier access to shopper data compared to Instant Checkout, which only offered transaction insights post-purchase.

Pfeiffer expressed reservations about the current ChatGPT app experience, noting that it “leaves a lot to be desired” and that its success as a model for AI shopping is not guaranteed. “Right now, I don’t see success in retail apps in ChatGPT,” she commented. “That doesn’t mean there won’t be. Adoption takes time.”

Early data suggests that while consumers are increasingly using AI chatbots for product research and recommendations, they are not completing purchases within the chat interface. A recent study by Adobe-owned Semrush found that only 22% of users have made a purchase directly within an AI tool, with half of respondents reporting that they made a purchase after using AI for research. Walmart reported that conversion rates were three times lower for products sold directly within ChatGPT compared to those that redirected users to the retailer’s website for checkout.

Etsy acknowledged that while ChatGPT has become a valuable discovery channel, purchase volume from Instant Checkout was relatively low due to the technology’s nascent stage. Pfeiffer believes that retailers with products suited for AI-driven experiences and who are seeing traffic from chatbots will likely invest in these platforms if feasible. For Etsy, a ChatGPT app could serve as an incentive for more sellers to join the platform by offering a new marketing channel.

Amazon: The Unaddressed Giant

Bank of America Securities analysts recently suggested in a research note that OpenAI’s new app-based approach “could enable more partners, such as Amazon,” by allowing retailers to better manage user experience and payments within ChatGPT. Amazon has recently deepened its ties with OpenAI, announcing a strategic partnership that includes an investment of up to $50 billion and making OpenAI’s AI models accessible to Amazon engineers for product development.

However, Amazon has simultaneously erected barriers to AI shopping partnerships, blocking numerous agents, including ChatGPT, from accessing its site. The company even sued Perplexity in November to prevent its Comet browser from scraping its website and making purchases on behalf of users. Perplexity has characterized Amazon’s lawsuit as an attempt to obstruct shoppers from using AI agents, arguing that these agents cannot be influenced by Amazon’s pervasive advertising or upsold to purchase additional items. Amazon continues to invest in its own AI tools, such as its Rufus shopping chatbot and “Buy for Me” agent, and has expanded its “Shop Direct” feature to allow consumers to browse and purchase items not sold on its platform.

As OpenAI refines its e-commerce strategy, Hetu advises consumers not to dismiss the company’s potential, despite intense competition. Pfeiffer reiterates that the broader landscape of AI shopping is still in its early stages, concluding, “Everyone thinks everyone else has this figured out, or is farther ahead of them. The fact is that no one has this figured out.”