Target Didn’t Announce an AI Feature. It Redefined Retail.
12 December 2025
Retail loves its buzzwords. Seamless. Omnichannel. Frictionless. Personalised. Headless!
The industry is forever rewriting the same playbook with new adjectives.
But every so often, something happens that isn’t a rewording of the familiar, but a reorientation of the whole terrain. Something small on the surface, but massive in its implications.
Target’s decision to build a full shopping journey inside ChatGPT is one of those moments, argues Tom Ollerton, founder of Automated Creative.
Not because it’s the first retailer to experiment with AI, it isn’t. But because it’s the first major retailer to act on a truth that most are still politely ignoring:
The website is no longer the front door. Intent has moved elsewhere. And if you want to meet it, you have to move too.
Target just made that shift visible.
1. A quiet announcement with loud consequences
Most AI shopping experiences have been gimmicks but Target’s launch felt different. An “app” inside ChatGPT that allows you to browse curated products, add multiple items to a basket, shop fresh food, and choose Drive Up, Pick Up or delivery. All conversational. All integrated.
In my Linkedin post Emma Linaker put it, this is “a sharp example of how fast the front door of retail is moving.” She’s right. It’s not about OpenAI or APIs or LLMs. It’s about the centre of gravity shifting from owned digital spaces to AI conversationals.
Target didn’t invent that shift. It simply accepted it.
2. The behaviour retailers wish wasn’t happening
For years, brands have operated under the same belief: that consumers can be shepherded from inspiration to product pages, from search ads to landing pages, from social to checkout. But behaviour has already broken free from these funnels. If you want to know what’s for dinner tonight, you ask an assistant. If you want recommendations, you can ask ChatGPT. If you’re planning a party, a trip, a wardrobe refresh, you increasingly start not with a retailer, but with an AI chat.
That’s the behavioural truth Target is responding to.
Jeric Griffin captured it precisely:
“Every company says they want to change user behavior, but they almost all go about it backwards. Target is using an in-progress shift in behavior instead of trying to reverse it.”
This is the heart of the move. Target isn’t trying to “train” consumers to use a new app or a new site flow. It’s simply following activity where it’s already happening. Retailers like to believe behaviour is a lever they pull; in reality, behaviour is a wave and you either ride it, or not.
Maya Moufarek put it even more simply:
“This is how you actually understand customer behaviour. Most brands are trying to get people to their website. Target went to where the behaviour already exists.”
3. Welcome to intent-first retail
Retail has always been defined by real estate. First, the store was the centrepiece. Then websites became the new front door. Then apps. Then marketplaces.
But now the most valuable real estate isn’t owned by retailers at all.
It’s the LLMs where intent sparks.
If more discovery, exploration, and decision-making happen inside an assistant, then the “place” consumers shop isn’t physical or digital. It’s the chat where they articulate desire. And that’s why Swagat Choudhury’s line struck such a chord “Store is no longer the only palace, you need to glamp up everywhere.”
Every retailer today has a choice, either cling to the idea that the journey begins on your website or accept that journeys now begin elsewhere, and if you want to be chosen, you have to appear where the question is asked, not where you wish it were asked.
Target made its choice.

4. What actually changes: UX, brand presence, and distribution
Here’s where the implications become deeper,not technical, but conceptual.
UX becomes linguistic, not visual
In a conversational environment, pages don’t exist. Shelves don’t exist. Navigation doesn’t exist. The user doesn’t click; they ask. Which is why Emma Linaker’s comment is the most important of the entire thread:
“Conversation becomes both media and shelf. UX is now language, prompts and guardrails, not pages and buttons.” That should unsettle retailers because they’ve spent 20 years mastering dropdown menus. Now they need to master dialogue design.
Brand becomes a suggestion, not a destination
Copywriter Shon-Lueiss Harris highlighted something nobody else mentioned: “ChatGPT creates a separation from the brand… this separation might still win the buy.” If an assistant mediates the interaction, the user’s relationship isn’t with the retailer, it’s with the assistant. Brand becomes a variable the AI includes or excludes depending on context. Some don’t like that idea. But it’s coming.
Distribution becomes proximity to intent, not ownership of traffic
For years, the holy grail was “drive them to our site”, now the holy grail is “be the answer to the question”. This changes everything from channel-led distribution to intent-led distribution. Target isn’t trying to own the traffic. It’s trying to own the moment.
5. The operational reality: AI is the easy part
There’s a temptation to talk about all this as if it’s a triumph of machine learning. But the cleverness isn’t in the AI; it’s in the supply chain. Maksym Levin cut straight to it: “The hardest part isn’t the AI, it’s the real-time integration required to execute fulfillment when the transaction happens outside the website.”
It’s true, it’s easy enough to create a conversational interface but harder to synchronise inventory, fulfilment, drive-up logistics and fresh food availability inside an environment you don’t control.
If Target is early, it’s not because it’s the most “innovative” it’s because it’s one of the few retailers with the infrastructure and discipline to make this work at all. Many retailers simply don’t have the plumbing.
6. The uncomfortable fork in the road
Here’s the unavoidable implication of all this. If customer intent lives inside AI assistants, then websites need a new job. They don’t die, but they stop being the starting point.
Jonathan Arena argued that this isn’t about replacing the website, but adding a new “iOS app” layer that acts in parallel. It’s a fair point. But parallel layers change behaviour too. When the upstream becomes more convenient than the destination, the destination must adapt.
My view is that websites need to work out their role in an AI search world. Playing to strengths is the best route. The high street didn’t disappear when e-commerce arrived. It just had to reinvent its purpose. Websites are now in the same position.
So what is their new role?
- To deliver depth, not discovery
- To house richer content, not basic answers
- To showcase brand, not capture intent
- To provide reassurance, not navigation
That is not a downgrade. It’s a repositioning. But pretending everything stays the same is not an option.
Tom will be writing a monthly column for MAD//Insight.

