Macy’s has rolled out a conversational AI shopping assistant called Ask Macy’s, built on Google’s Gemini Enterprise platform, after a pilot that began in December 2025 and a full launch the department store chain timed to the Shoptalk retail conference in March 2026. According to figures the company shared with Google and reported by trade outlets, customers who engaged with Ask Macy’s during the beta period generated 4.75 times more revenue per visit than those who shopped without it — a jump some coverage rounded to roughly a 400% increase in spending among engaged users.
A Four-Week Sprint to Launch
The origin story Macy’s and Google have told publicly is notably fast-moving for a legacy retailer: Macy’s engineering team had already spent close to six months building its own website shopping-agent project when it learned about Gemini Enterprise for Customer Experience, concluded the platform was a strong fit, and pivoted into a rapid development sprint that produced the shippable version of Ask Macy’s in about four weeks. The tool is accessible through Macy’s e-commerce site and mobile app, where it handles conversational product discovery, personalized recommendations, and a virtual try-on feature that lets shoppers see how apparel might look before buying.
How It’s Meant to Work
Instead of browsing Macy’s site through traditional category filters, a shopper can describe what they want in natural language — an outfit for a specific occasion, a gift in a certain budget, a brand they already like — and Ask Macy’s returns tailored product suggestions pulled from live Macy’s inventory and catalog data. The virtual try-on component, layered on top of the conversational engine, is aimed at addressing one of apparel e-commerce’s oldest problems: shoppers hesitating to buy clothing they can’t physically try on.
Why the Spending Numbers Matter
For a department store chain that has spent years closing stores and fighting an narrative of decline against off-price and online-first rivals, a shopping tool that multiplies revenue per visit by nearly five times is a striking data point — and Macy’s and Google have been eager to publicize it as proof that generative AI can move beyond customer-service cost-cutting into an actual sales driver. Macy’s is framing Ask Macy’s as a core part of its digital strategy going forward rather than a side experiment, and the company’s public comments suggest it intends to keep expanding the assistant’s capabilities.
The Caveats Behind a Flashy Number
Retail analysts caution that early-adopter spending figures from a beta period often look stronger than what a tool delivers once it reaches a company’s full customer base, since the first wave of users engaging with a new AI feature tends to skew toward shoppers who were already more engaged or ready to buy. There are also open questions about how Ask Macy’s handles product data accuracy — a conversational agent recommending an item that’s actually out of stock, mis-described, or priced incorrectly creates a different kind of customer frustration than a traditional search filter ever could. Consumer advocates have separately raised concerns about how AI shopping assistants across retail are using browsing and purchase history to personalize recommendations, and what data retailers like Macy’s share with the AI vendors — in this case Google — powering the underlying models.
Part of a Broader Retail AI Race
Macy’s is hardly alone in pushing conversational AI into the shopping experience. Walmart has its own assistant, Sparky, handling tasks like assembling grocery baskets, and the industry’s broader shift toward “agentic commerce” — AI systems that don’t just recommend products but can complete purchases on a shopper’s behalf — is accelerating across big-box and department store chains alike in 2026. What sets Macy’s case apart so far is the speed of development and the size of the reported spending lift, both of which other retailers will likely be watching closely as they weigh their own AI shopping investments.
What Comes Next
Macy’s has not said when Ask Macy’s will reach all of its stores’ online customer base or whether the virtual try-on feature will expand to its full apparel catalog. The company’s public messaging suggests continued investment is likely, particularly if the revenue-per-visit gains hold up as more shoppers — not just early adopters — start using the tool. The coming year will show whether Ask Macy’s represents a durable shift in how department stores sell clothes online, or an AI-era honeymoon number that settles once the novelty wears off.
Photo: PIRO4D / PIXABAY via Pixabay
