ChatGPT’s First Holiday Season

Technically you could argue the first holiday season was last year. However, the flurry of announcements and new shopping-specific functionality to try out clearly makes 2025’s holiday season the year shopping agents debuted. OpenAI productized “Shopping Research” to all global users on Nov. 24, just in time for Black Friday Cyber Monday (BFCM), perhaps the most important shopping weekend of the retail calendar. Along with Walmart’s launch on ChatGPT Instant Checkout, and Target’s app embedded within ChatGPT, it’s been a busy stretch in the Agentic AI world. Here’s a brief recap of the announcements:

• Shopping Research: The new feature assists consumers’ product discovery through selected price ranges, product features and other specifics, to produce side-by-side comparisons, retailer links and inventory availability. OpenAI’s press release and video demo can be found here.
• Walmart: launched Nov. 30, customers can now shop Walmart through ChatGPT using Instant Checkout. This follows Walmart’s October announcement of their partnership with OpenAI that includes the unprecedented decision to share customer data in order to gain first mover advantage. Walmart’s press release can be found here.
• Target: launched in beta during Black Friday week, Target offers a complete shopping experience through its app in ChatGPT. Personalized recommendations are coming soon. Target’s Press release can be found here.

Image Source: Target

It should be noted that the rollout of these shopping features will vary by region and the ChatGPT version you’re using. (paid/non-paid). If you do have access, early reviews of the shopping experience are inconsistent as bugs are worked out. ChatGPT is not the only answer engine to add shopping features. Perplexity and PayPal announced a partnership to enable Instant Buy. And Rufus’ “Compare” mode provides a similar way to research product feature sets. All should be considered in beta for now, but clearly the Agentic AI shopping race is under way! Retailers of all sizes should now be on alert as they see the biggest players set the bar – for now.

What impact will this have on retailers and how they manage their ecommerce sites? It’s still early, but one short term opportunity is to provide deeper FAQ-like content to product detail pages – note the variants used to ask the shopper their preferences – and whether that information is readily available for answer engine crawlers to find.

Over the longer term, what does this mean to the emotional side of shopping and managing the customer experience? The “art” in balanced “art-and-science merchandising”? We look forward to addressing merchandising fundamentals in an Agentic AI world, as we get through the holiday season and see how retailers fared.

Where is your company at in planning and prioritizing for Agentic AI and more AI transformation? Ask McMillanDoolittle about our AI Immersion Workshops to explore C-suite governance and strategy options, aligned to your corporate strategy.