The news: Microsoft overhauled its Digital Direct Sales operation—responsible for selling all first-party products on Microsoft.com across 100+ markets—to run on an AI-first model that drives the company’s ecommerce.

The strategy, which was demoed at Contentsquare’s CX Circle last week, is anchored in four pillars: product breadth, differentiation, geographic focus, and end-to-end experience.

Microsoft’s pivot mirrors retail’s rapid generative AI (genAI) adoption. A quarter (24%) of consumers have used genAI to shop—up from 20% last year—and 35% plan to try it soon. Awareness is growing fast too: Only 20% of adults say they’re unaware of genAI shopping tools, down from 28% in 2023, per Capgemini.

AI agents solve shopping bottlenecks: Kelly Soligon, VP of digital direct sales for Microsoft, described a near-term future where consumers no longer “browse” or “search” in the traditional sense. Instead, they enter a conversation with an AI agent—on Microsoft.com, Copilot, or even external platforms like ChatGPT—and expect instant, context-aware help on their path to purchase.

Microsoft’s AI assistant parses 4 million customer feedback items and has lifted conversions by 90% while cutting costs 30%, per Soligon. The AI assistant supports natural dialogue, persona-based guidance (e.g., student, engineer), and handoff to humans for complex queries to yield the following benefits:

• AI-driven insights. A high-quality feedback model translates millions of user comments into measurable site improvements, linking problems like promo-code failures directly to checkout KPIs.
• Personalization at scale. Using “Personal Gen 2” standards, Microsoft is expanding from one-off A/B tests to full-catalog optimization—adjusting add-ons, pricing, and preorder offers dynamically.

Our take: The next battle for customer intent won’t happen on search bars or landing pages—it will happen inside conversations. The brands that train their AI agents to listen, reason, and personalize at scale will own those moments of intent.