Retailers who ignore AI-native shopping interfaces are already losing customers to the ones who don’t make them think.

The checkout friction nobody talks about publicly

Shoppers abandon carts when discovery takes too long and checkout has too many steps. Store associates lose time on repetitive guest questions that a well-trained model could answer in seconds.

Target just moved the shopping cart into ChatGPT

OpenAI and Target team up on new AI puts a dedicated Target experience inside ChatGPT, where shoppers describe what they need and receive personalized product recommendations with a faster path to purchase. On the enterprise side, Target is expanding its use of ChatGPT Enterprise so internal teams can cut through operational busywork and spend more time on guest-facing work. The input is a conversational prompt; the output is a curated product selection or a completed workflow, depending on which side of the counter you’re standing on.

Three teams inside retail feel this first

• E-commerce merchandisers who manually curate product collections and need AI to surface the right SKUs faster for seasonal pushes
• Store operations managers who spend hours fielding internal process questions that a trained enterprise model can resolve without escalation
• Digital product teams at competing retailers who now have a benchmark they did not have six months ago

The pressure is not theoretical. It is already in the app store.

Walmart moved first, but Target just closed the gap

Walmart has been running AI shopping experiments for over a year, and Amazon’s Rufus assistant crossed 10 million queries within weeks of launch. A major national retailer embedding ChatGPT natively into its app signals that conversational commerce is no longer a pilot program — it is becoming the expected interface.

What you can actually do with this

• Ask ChatGPT to build a Target cart based on a specific occasion or budget
• Get personalized product recommendations without opening the Target app separately
• Use ChatGPT Enterprise internally to answer store ops and HR process questions at scale
• Reduce guest service response time by routing common questions through AI before a human steps in

Pricing for the consumer-facing Target app integration is not listed separately — check the ChatGPT app for availability, and check our directory for enterprise pricing details.

The one thing this cannot replace yet

Conversational AI still struggles with highly specific in-store availability queries, so shoppers checking real-time local inventory will still hit friction.

The rest of retail is watching this quietly

For teams not inside retail, Google’s Shopping Graph and Perplexity‘s product search are approaching the same problem from the search side rather than the app side. The difference here is that Target owns the checkout relationship, which gives it data leverage that a pure search player does not have.

Retail AI is moving from pilot programs to permanent infrastructure

The gap between retailers with AI-native shopping and those running legacy apps is widening faster than most product roadmaps anticipated. We cover tools like this every Friday — subscribe here and we’ll send the best ones straight to you.