What is an AI retail shopping assistant? An AI retail shopping assistant is a conversational chatbot powered by large language models that guides customers through product discovery, personalized recommendations, and purchasing decisions using natural language. Macy's just proved this technology can transform retail economics: its Google Gemini-powered "Ask Macy's" chatbot drove customers to spend 4.75 times more than non-users, according to data presented at Shoptalk 2026. For CRE retail investors, this is the most concrete evidence yet that AI can revitalize anchor tenant performance and reshape mall valuations. For a broader view of AI's role in commercial real estate, see our complete guide on AI tools for commercial real estate investors.
Key Takeaways
- Macy's "Ask Macy's" AI shopping assistant, powered by Google Gemini, increases customer spending by 4.75x compared to non-users.
- About 40% of the top 20 U.S. retailers by revenue have deployed AI shopping assistants as of early 2026, signaling a permanent shift in retail operations.
- AI-driven spending lifts directly improve anchor tenant health, which drives co-tenancy clauses, foot traffic, and retail CRE net operating income.
- Retailers that fail to adopt AI shopping tools risk accelerating the decline cycle that has already shuttered thousands of stores since 2020.
- CRE investors should evaluate retail tenants based on AI adoption maturity, not just traditional sales-per-square-foot metrics.
How Macy's AI Shopping Assistant Works
Macy's launched "Ask Macy's" publicly in March 2026 after piloting internally since December 2025. Built on the Google Gemini platform, the tool lets shoppers describe what they need in plain language. A customer might type, "I need a dress for a spring wedding in Miami under $150," and the AI surfaces curated product recommendations, styling ideas, and "complete the look" suggestions with links to complementary items.
According to Macy's Chief Customer and Digital Officer Max Magni, the tool is "not about search" but about "curated discovery." The AI asks follow-up questions such as "Do you prefer bright colors or calm colors?" to refine recommendations. This conversational approach increased average basket size dramatically because the assistant guides customers toward full outfits rather than individual items.
The 4.75x spending figure came from testing with approximately half of Macy's website visitors over several weeks, as reported by Fortune and Bloomberg. The data is significant both in magnitude and sample size.
Why This Matters for CRE Retail Investors
Macy's operates approximately 500 stores across the United States, serving as an anchor tenant in hundreds of malls and shopping centers. Anchor tenant health directly determines the viability of entire retail properties through co-tenancy clauses, foot traffic generation, and lease renewal probability. When an anchor like Macy's thrives, surrounding tenants benefit from increased shopper visits. When anchors struggle, the cascade effect can devastate a property's NOI.
The 4.75x spending lift from AI has three direct implications for retail CRE:
- Higher Sales Per Square Foot: If AI-assisted customers consistently spend nearly five times more, Macy's revenue per location could increase substantially. This strengthens lease renewal negotiations and supports percentage-rent structures where landlords earn a share of tenant sales above a baseline threshold.
- Reduced Store Closure Risk: Macy's has closed over 150 stores since 2020. Higher AI-driven spending could slow or reverse this trend by making marginal locations profitable again. For landlords with Macy's as an anchor, AI adoption lowers the probability of the vacancy scenario that CRE investors fear most.
- Omnichannel Synergy: The "Ask Macy's" tool is available across digital platforms and the mobile app, but it also influences in-store behavior. Store associates now use similar AI tools to assist customers during fitting sessions, bridging the online and physical retail experience. This omnichannel approach supports the case for maintaining physical retail locations rather than consolidating to e-commerce only.
The Broader Retail AI Wave
Macy's is not an isolated case. According to PwC research, approximately 40% of the top 20 U.S. retailers by revenue have deployed some form of AI-powered shopping assistant as of early 2026. Major deployments include:
- Shopify Agentic Storefronts: Merchants can now sell directly inside ChatGPT, Google AI Mode, and Microsoft Copilot, with Shopify reporting 7x AI traffic growth and 11x order growth since January 2025. CRE investors can learn more about this shift in our analysis of Shopify agentic storefronts in ChatGPT.
- Walmart and OpenAI: Walmart tested ChatGPT-powered in-app shopping but found it converts at one-third the rate of its own website, pivoting to branded AI experiences instead. See our coverage of Walmart's ChatGPT shopping results for the full breakdown.
- Gap, DoorDash, and Wayfair: All three retailers are leveraging Google Gemini for AI-powered product discovery and recommendation engines.
- Apple Maps Paid Ads: Apple is launching paid search ads in Apple Maps for U.S. and Canadian retailers, creating a new AI-driven foot traffic channel. Our analysis of Apple Maps paid ads for retail CRE explores the implications.
The trend is clear: retailers are racing to deploy AI assistants not as experiments but as core revenue drivers. For CRE retail investors, a tenant's AI adoption maturity is becoming as important as its credit rating.
How to Evaluate Retail Tenants on AI Readiness
CRE investors analyzing retail properties should add AI readiness to their due diligence checklist. Here are five signals to assess:
- Conversational AI Deployment: Does the tenant offer an AI shopping assistant on its website and app? If so, what platform powers it (Google Gemini, OpenAI, proprietary)?
- Omnichannel Integration: Is the AI tool connected to in-store experiences, or is it siloed to e-commerce? Tenants with integrated systems are more likely to maintain physical locations.
- Spending Lift Data: Has the tenant publicly reported AI-driven spending increases? Macy's 4.75x figure sets a high benchmark, but even a 1.5x to 2x lift signals meaningful adoption.
- Technology Partnerships: Tenants partnered with Google, Microsoft, or Anthropic for AI tools have access to frontier model capabilities that smaller competitors may lack.
- Store Associate AI Tools: Retailers equipping floor staff with AI assistants for real-time inventory lookup, styling recommendations, and customer profiling are investing in the physical store experience.
For personalized guidance on evaluating AI-ready retail tenants in your portfolio, connect with The AI Consulting Network.
Financial Impact Scenarios for Retail CRE
To illustrate the potential impact, consider a simplified scenario for a 100,000-square-foot Macy's anchor location generating $200 per square foot in annual sales ($20 million total).
If AI shopping assistants increase average spending by even a conservative 2x (not the full 4.75x, accounting for adoption rate), and 30% of customers engage with the AI tool, the blended revenue lift would be approximately 30% of customers multiplied by the incremental spending. That translates to roughly $6 million in additional annual sales at this single location.
For landlords with percentage-rent structures (typically 2% to 5% of sales above a breakpoint), this could mean $120,000 to $300,000 in additional annual rent per location. Applied across a portfolio of 10 Macy's-anchored properties, the NOI impact becomes material. At a 6.5% cap rate, that additional NOI translates to $18.5 million to $46.1 million in incremental property value across the portfolio.
These are illustrative estimates, but they demonstrate why AI-driven retail performance deserves attention in CRE underwriting models. CRE investors looking for hands-on AI implementation support can reach out to Avi Hacker, J.D. at The AI Consulting Network.
Risks and Limitations
The 4.75x spending figure, while striking, comes with important caveats:
- Selection Bias: Customers who engage with an AI shopping assistant may already be higher-intent shoppers. The spending lift likely reflects both AI effectiveness and user self-selection.
- Early Adopter Effect: As AI assistants become ubiquitous, the novelty factor may diminish. The spending lift could normalize over time.
- Platform Dependency: Macy's reliance on Google Gemini creates technology concentration risk. Changes in API pricing, model capabilities, or partnership terms could affect performance.
- Privacy Concerns: AI shopping assistants collect detailed preference data. Regulatory changes around AI data collection could constrain these tools.
Despite these caveats, the directional signal is powerful. AI shopping assistants represent a genuine revenue catalyst for retail tenants, not just a cost-cutting measure.
What Comes Next for AI in Retail CRE
The AI in real estate market is projected to reach $1.3 trillion by 2030, growing at a 33.9% CAGR (Source: Precedence Research). Within retail specifically, agentic AI is emerging as the next phase, where AI systems autonomously handle procurement, inventory management, pricing optimization, and event programming without human intervention.
For CRE investors, this evolution means that retail properties with tenants who embrace AI will increasingly outperform those with tenants who do not. The gap between AI-adopting and AI-resistant retailers will widen through 2026 and beyond, making tenant AI maturity a leading indicator of property performance. If you are ready to integrate AI metrics into your retail CRE investment strategy, The AI Consulting Network specializes in exactly this.
Frequently Asked Questions
Q: How does Macy's AI shopping assistant actually increase spending by 400%?
A: The "Ask Macy's" chatbot, powered by Google Gemini, guides customers through curated product discovery using natural language. Instead of browsing passively, customers describe their needs and receive complete outfit recommendations, styling ideas, and complementary product suggestions. This "complete the look" approach increases basket size by encouraging customers to purchase coordinated items rather than single products.
Q: Does the 4.75x spending lift apply to all customers or just a subset?
A: The 4.75x figure compares spending between customers who engaged with the AI assistant and those who did not, based on testing with approximately half of Macy's website visitors. Some selection bias is likely, as higher-intent shoppers may be more inclined to use the tool. However, the magnitude of the lift suggests the AI is genuinely influencing purchase behavior, not just capturing pre-existing intent.
Q: Which other retailers are deploying AI shopping assistants?
A: As of early 2026, approximately 40% of the top 20 U.S. retailers by revenue have deployed AI shopping assistants. Notable examples include Shopify merchants selling inside ChatGPT, Walmart testing ChatGPT-powered shopping, and Gap, DoorDash, and Wayfair using Google Gemini. The trend is accelerating rapidly across both department stores and specialty retailers.
Q: How should CRE investors adjust their underwriting for AI-enabled retail tenants?
A: Investors should add AI readiness to their tenant evaluation criteria, including whether the tenant has deployed conversational AI, the platform powering it, any reported spending lifts, and the level of omnichannel integration. Properties anchored by AI-adopting tenants may warrant tighter cap rates due to lower vacancy risk and higher potential revenue growth.
Q: Could AI shopping assistants accelerate store closures by shifting spending online?
A: The evidence so far suggests the opposite. Macy's AI tool bridges online and in-store experiences, with store associates using similar AI capabilities during in-person consultations. Retailers are deploying these tools to complement physical locations, not replace them. The key risk for physical retail is not AI adoption but the failure to adopt, which leaves tenants unable to compete with AI-enabled competitors.