The Agile Brand with Greg Kihlström®: Expert Mode Marketing Technology, AI, & CX

Episode #746: Personalizing the DTC Customer Experience with Kelly Sulligan, Microsoft
Release Date: October 6, 2025

Episode Overview

In this episode, Greg Kihlström sits down with Kelly Sulligan, VP of Consumer Digital Direct Sales at Microsoft, live from Content Square's CX Circle in New York City. The conversation zeroes in on how Microsoft leverages artificial intelligence and advanced personalization to transform its Direct-to-Consumer (DTC) experience at scale. Sulligan shares practical insights from Microsoft's journey with AI innovation, explores the future of agent-based commerce, and reflects on maintaining agility—and curiosity—in a fast-paced industry.

Key Discussion Points and Insights

1. The Evolution of Personalization and AI at Scale (02:46–07:32)

• AI-Driven Feedback Analysis

  • Microsoft receives over 4 million pieces of customer feedback annually from various channels.
  • AI is used not just for volume management, but to sift, clarify, and prioritize high-quality, actionable insights.
  • Quote:
    “We're using AI to help us identify high quality feedback and then quickly take action on it to improve our customer experience.”
    —Kelly Sulligan (03:15)

• Virtual Store Assistant Transformation

  • Microsoft replaced their traditional chatbot with a generative AI-powered Virtual Store Assistant, introducing a more natural, contextual customer interaction.
  • This assistant can:
    • Answer customer questions in human terms.
    • Offer compare charts and product configurations.
    • Guide purchases and support queries in a seamless conversation.
  • Quote:
    “It’s been a really great high satisfaction experience for our customers.”
    —Kelly Sulligan (04:12)
  • Planning further expansion with voice and vision-based interfaces.

• Personalization Embedded Throughout the Customer Journey

  • Transitioned from isolated experimentation to embedding personalization as a core business capability.
  • AI models use high-intent signals (e.g., adding to cart) to optimize product recommendations and offers.

2. Achieving Personalization at Massive Scale (05:05–07:32)

• Scalability Through AI

  • Manual one-off experiments could not keep up with Microsoft’s volume.
  • AI models now automate and optimize engagement at scale—a necessity, not a bonus.
  • Focus has shifted to personalizing around “high-value engagements”—add to cart, cart completion, etc.—for meaningful business outcomes.

• Strategic Application of Personalization

  • Not everything should (or can) be personalized.
  • Assess where personalization creates measurable business impact before deploying resources.
  • Quote:
    “You could personalize everything... but is it really resulting in measurable business impact?”
    —Kelly Sulligan (07:32)

3. Rise of Agentic Commerce and Virtual Agents (08:13–10:34)

• Generative AI Agents Enhance Buyer Experience

  • Over 1.7 million customer interactions with the new Virtual Store Assistant.
  • Agents walk customers through decision-making in easy-to-understand language—away from confusing tech specs.
  • Provide support for order status, returns, and automatically escalate to humans when needed.
  • Considering future where agents become the “front door” to Microsoft.com, replacing navigation/search with conversation.

• Balanced Automation and Human Touch

  • Recognizes that some customer needs are best served by humans—AI agents facilitate smooth handoffs for superior experiences.

4. Critical Success Factors for AI Agents (11:26–13:14)

• Three Pillars for Agent Success:
  1. Clear Intent & Guardrails
     • Clearly define the use case and parameters for the agent.
  2. Data Quality & Governance
     • Prioritize robust data models and data governance for accuracy, transparency, and privacy.
  3. Human Oversight & Optimization
     • Continuous human involvement to monitor, assess, and tweak agent behaviors and models.
  • Quote:
    “You can’t just set it and forget it. You need to have the right level of human monitoring and checking the customer experience.”
    —Kelly Sulligan (12:41)

5. Voice of Customer: Reconciling Feedback & Behavior Data (13:14–16:47)

• Contradictory Signals: Survey vs. Behavior

  • Example: Post-purchase surveys show 5-star satisfaction, but transactional data reveals high product return rates.
  • Lesson: Combine subjective feedback with objective behavior/KPI data to identify true pain points.
  • Quote:
    “People who fill out surveys, for the most part they're either super happy or they're super mad.”
    —Kelly Sulligan (14:14)

• Actionable Feedback Identification

  • AI flags feedback that is specific, actionable, and tied to real experiences for analyst review.
  • Further prioritization by linking feedback to high-value engagements (e.g., add to cart).
  • Mental Model: Focus first on what’s actionable, high-impact, and realistically fixable.

6. The Near Future of AI in E-Commerce (16:47–19:45)

• Changing Consumer Search & Buying Behaviors

  • Shift from web/site-based search to using AI agents like Copilot or ChatGPT for product discovery and advice.
  • Agent-driven and agent-influenced commerce (e.g., ChatGPT partnered with Shopify and Stripe for commerce in-chat)—becomes an emerging channel.
  • Quote:
    “If I’m experiencing that, millions and zillions of other people are experiencing that as well too. And so we in E-commerce have to adapt for that.”
    —Kelly Sulligan (17:31)

• Advice for E-Commerce Leaders

  • Prepare product data and APIs for seamless integration with these agents and ecosystems.
  • Experiment actively—don’t wait for the trend to stabilize.

7. Staying Agile as a Leader (20:01–21:55)

• Personal Wellbeing Enables Agility
  • Sustained agility requires personal energy. Sulligan prioritizes daily exercise and self-care.
  • “Put your mask on first”—taking care of oneself to be best positioned for adaptive leadership.
• Cultivated Curiosity for Innovation
  • Regularly seeks diverse perspectives, both inside and outside the industry.
  • Schedules coffee chats several times a week to learn from others—source of breakthrough ideas.
  • Quote:
    “If you keep listening to yourself and hearing the same thing over and over again, you get the same results. That’s not where breakthrough comes.”
    —Kelly Sulligan (21:37)

Notable Quotes (with Timestamps)

• “We're using AI to help us identify high quality feedback and then quickly take action on it to improve our customer experience.” —Kelly Sulligan (03:15)
• “It’s been a really great high satisfaction experience for our customers.” —Kelly Sulligan (04:12)
• “Without AI you can’t do [personalization] at scale.” —Kelly Sulligan (05:49)
• “You could personalize everything... but is it really resulting in measurable business impact?” —Kelly Sulligan (07:32)
• “You can’t just set it and forget it. You need to have the right level of human monitoring and checking the customer experience.” —Kelly Sulligan (12:41)
• “People who fill out surveys, for the most part they're either super happy or they're super mad.” —Kelly Sulligan (14:14)
• “If I’m experiencing that, millions and zillions of other people are experiencing that as well too. And so we in E-commerce have to adapt for that.” —Kelly Sulligan (17:31)
• “If you keep listening to yourself and hearing the same thing over and over again, you get the same results. That’s not where breakthrough comes.” —Kelly Sulligan (21:37)

Timestamps for Key Segments

• 02:46 – AI-driven customer feedback and personalization innovations
• 04:12 – Launch and impact of Microsoft’s generative AI Virtual Store Assistant
• 05:49 – How AI enables personalization at scale
• 07:32 – Prioritizing personalization for measurable business outcomes
• 08:40 – Agentic commerce and its implications for both customers and employees
• 12:41 – Success factors for deploying AI agents
• 13:31 – Reconciling voice of customer and behavioral data
• 17:13 – How AI is transforming consumer search and purchase behaviors
• 20:01 – Leadership strategies for maintaining agility and curiosity

Flow and Tone

The episode delivers practical, optimistic, and reality-checked perspectives. Sulligan’s tone remains personable, curious, and candid throughout, offering real-world examples and actionable advice for marketing leaders navigating AI-powered transformation in DTC and e-commerce.

For further resources and details on this episode’s topics, visit Microsoft’s digital commerce resources or follow The Agile Brand podcast.