What is Ask Macy's and how does it work?

Ask Macy's is an AI-powered shopping assistant designed to act more like a personal stylist than a traditional search bar. Customers can describe what they need conversationally—for a prom, vacation, or last-minute event—and receive curated recommendations informed by their past purchases, preferences, and context.

How does Macy's AI-first approach differ from how retailers used AI before?

Rather than layering AI onto existing workflows, Macy's is embedding intelligence directly into systems that include personalization, search, operational planning, and software development itself. This redesign compresses the gap between gathering a signal and taking action, allowing the business to move faster.

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Macy's is embedding AI directly into its core business systems—search, inventory, and product recommendations—rather than bolting it on as an afterthought, signaling a broader shift in how retail makes decisions.

MIT Technology Review AI13h ago5 min read

Key takeaway

Macy's is redesigning its core business systems to embed AI directly into decision-making, rather than adding it on top of existing workflows. This "AI-first" philosophy—being adopted across retail—aims to make the company move faster and personalize customer experiences by default, with early successes in search recommendations and customer engagement now scaling into conversational shopping tools.

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3 Key Points

What happened
Macy's has adopted an "AI-first" approach that embeds intelligence directly into systems for personalization, search, operational planning, and software development. The company is extending this into conversational commerce with Ask Macy's, an AI-powered shopping assistant that makes recommendations based on past purchases and context.
Why it matters
Rather than treating AI as a layer on top of existing workflows, retailers like Macy's are redesigning how decisions happen to move faster and make every customer experience feel more relevant by default. This shift from isolated AI pilots to integrated systems is compressing what the company calls "the gap between the signal and the action," meaning insights translate into action more quickly.
What to watch
Macy's sees AI as an invisible layer augmenting human judgment rather than replacing it. The company views long-term success as continuous improvement—learning from mistakes, adapting to new technology standards, and timing execution so that changes compound into a meaningfully better customer experience.

FAQ

What is Ask Macy's and how does it work?: Ask Macy's is an AI-powered shopping assistant designed to act more like a personal stylist than a traditional search bar. Customers can describe what they need conversationally—for a prom, vacation, or last-minute event—and receive curated recommendations informed by their past purchases, preferences, and context.
How does Macy's AI-first approach differ from how retailers used AI before?: Rather than layering AI onto existing workflows, Macy's is embedding intelligence directly into systems that include personalization, search, operational planning, and software development itself. This redesign compresses the gap between gathering a signal and taking action, allowing the business to move faster.

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