AI in Retail: What Executives Should Learn from Early Leaders

by Eric Postow, Esq. Chair AI Practice Group

Retail appears to be a ground zero for enterprise AI and it’s moving faster than many executives realize. Whether you’re in healthcare, logistics, or finance, what retail is doing today is worth understanding within your industry. The retail playbook reveals key patterns: how AI reshapes operations, interfaces with customers, and redefines efficiency. If your sector hasn’t yet felt the full weight of these changes, it soon will, and the lessons from retail offer a roadmap to readiness.

Who’s out front (and what they’re actually doing)

Starbucks is rolling out AI-powered, computer-vision inventory counting across more than 11,000 North American company-owned stores, enabling counts eight times more frequently and reducing out-of-stocks. The system (with NomadGo) blends 3D spatial intelligence, computer vision, and AR, and is part of a broader in-store AI operations stack.

Walmart has been public about scaling generative AI across shopper and associate experiences—search and assistant functions in the app, adaptive retail personalization, and workflow automation—framed as a platform strategy rather than a set of tools.

Sam’s Club, part of Walmart, has deployed AI-powered exit technology (receipt verification) at scale to remove a persistent friction point, an example of AI directly improving member experience in physical retail.

Target and The Home Depot highlight the broader retail shift from reactive inventory to predictive systems, using AI to forecast, prevent stockouts, and tighten replenishment, now a board-level reliability and margin question.

Ralph Lauren launched Ask Ralph, a brand-controlled AI stylist inside its U.S. app, personalizing outfits through a conversational assistant trained on the brand’s own creative and product data. It’s a blueprint for owned-voice personalization.

Morrisons in the U.K. rolled out a Google Gemini-based Product Finder that guides shoppers to the right aisle or shelf, showing AI’s value in wayfinding and micro-convenience.

The three dominant trends (and why they matter beyond retail)

Inventory and Supply: from reactive to predictive to autonomous

What’s happening: Vision systems and forecasting models are moving retailers from periodic, manual counts to continuous, machine-assisted visibility and from static replenishment to dynamic, store- and SKU-level predictions.

Why it travels cross-industry: Any multi-site, multi-SKU (or multi-asset) business, consumer goods, healthcare, field services, manufacturing, benefits from the same transition: instrument reality, forecast, automate decisions.

Personalization and Customer Engagement: brand-safe generative AI

What’s happening: Retailers are bringing generative AI into brand-owned channels (apps, sites, loyalty programs) to recommend, style, and advise, under tight voice and guardrails.

Why it travels: Financial services, hospitality, and healthcare can adapt the model of conversational, context-aware assistants that operate within compliance and brand tone.

E-commerce and Storefront Orchestration: frictionless journeys

What’s happening: AI is cutting front-of-house friction, such as Sam’s Club’s exit tech, and powering adaptive search and assistance that shorten the path from intent to purchase.

Why it travels: Anywhere customer experience involves a queue, a form, or a search box, AI can compress steps and surface the next best action.

Final Observation

Retail is an early indicator of how AI adoption can drive strategic differentiation. By zeroing in on the fundamentals including supply management, customer experience, and process efficiency, global retailers like Starbucks are showing what the future of mass adoption may look like across the industry.

How Holon helps

Holon Law Partners works across highly regulated industries where AI intersects with compliance, infrastructure, and risk. Our core strength is guiding leaders through corporate transactions and regulatory complexity while aligning innovation with long-term business strategy. We bring a holistic approach integrating governance, contracting, partnerships, workforce strategy, intellectual property, and change management, so your organization can not only adopt AI responsibly, but also scale it as a strategic asset. In an era where survival may mean restructuring, merging, or reinventing your business model, Holon helps C-suites and leadership teams move with clarity, integrity, and confidence.

Save the Date: Leaders in the greater New York City area, please join Holon Law Partners and EisnerAmper in January 2026, for a moderated C-suite roundtable on “AI and the C-Suite.” We’ll dig into what executives must know, how to structure talent and governance, and where to act first. For more information or to be added to the event list, please email aibreakfast@holonlaw.com.

Additional Sources

• Reuters. “Starbucks rolls out AI for inventory counting.” September 2025.
• Starbucks. “How AI-powered automated counting is brewing a better experience at Starbucks.” 2025.
• Times of India. “Walmart’s AI super agents promise smarter shopping and faster digital growth in e-commerce.” 2025.
• Business Insider. “To avoid product shortages, big retailers are scrapping reactive methods for AI.” June 2025.
• Vogue Business. “Inside Ralph Lauren’s new white-label AI styling tool.” 2025.
• Wall Street Journal. “Ralph Lauren Has Entered the AI Age.” 2025.
• The Sun. “Morrisons’ new shopping tool.” 2025.
• MySanAntonio. “Sam’s Club Scan & Go expansion.” 2025.
• New York Post. “Sam’s Club reveals plan to eliminate checkout lanes completely.” April 2025.