The Agile Brand with Greg Kihlström®

Episode #755: Sitecore CMO Michelle Boockoff-Bajdek and Microsoft's Talisha Padgett on Designed Intelligence for Marketing
Release Date: October 23, 2025
Guests: Michelle Boockoff-Bajdek (CMO, Sitecore); Talisha Padgett (GM, MarTech AI and Automation, Microsoft)

Episode Overview

In this episode, Greg Kihlström hosts Sitecore’s CMO, Michelle Boockoff-Bajdek, and Microsoft’s Talisha Padgett for a deep dive into the intentional design of AI in marketing. The discussion centers on moving beyond the hype of AI toward creating collaborative, human-centric frameworks that drive relevant customer experiences, bridge organizational silos, and ensure trust, empathy, and ethical responsibility at scale. The episode offers a preview of topics to be discussed at the upcoming Sitecore Symposium.

Key Discussion Points & Insights

1. Shifting from Segments to Signals

Timestamps: 03:31–04:42

• The guests explore how marketing must evolve from traditional static segments to dynamic, real-time signals:
  • Michelle Boockoff-Bajdek:

    “Traditional segments told us who the customer was, but signals tell us what they're doing right now. … We have to bring it all together … Clicks, searches, social interactions, purchases.” (03:44)

  • Emphasizes the culture shift required, breaking down barriers between marketing, sales, product, and data teams to build a “living, breathing picture of the customer.”

2. Designed Intelligence: Human + AI Collaboration

Timestamps: 04:44–07:04

• The panel contextualizes AI as a partner amplifying human creativity and empathy, not just automation:
  • Michelle Boockoff-Bajdek:

    “It is an intentional choreography ... Technology like Sitecore can clear the noise so we can focus on the moments that matter.” (05:20) “Let's use machines for what they do best—speed, scale, precision. And then let's let humans do what we do best, which is connect, create, and act.” (05:49)

  • Talisha Padgett:

    “AI is not something that people should be fearful of if used in the correct way. It really does empower humans to think more about what they would want in an experience.” (06:30)

3. Addressing Fears and De-Risking AI Investment

Timestamps: 07:04–09:51

• Discussion focuses on why enterprises hesitate adopting AI, and how the Sitecore AI Innovation Lab empowers organizations:
  • Talisha Padgett:
    • Most hesitation comes from not knowing how to start or align AI to business goals.
    • Recommends small pilot projects (“labs”) to surface process or role changes and demystify AI’s impact.

      “All three of those things have to work together—people, process, and technology ... these labs are a great way to get started.” (08:40)

  • Michelle Boockoff-Bajdek:
    • Fears are less about capability and more about control over data and brand voice.

      “Labs give brands this safe, guided environment to explore before they deploy … We work alongside and prototype and pressure test and fine tune.” (09:25)

4. Real-World Examples of Human-AI Collaboration

Timestamps: 09:53–12:33

• The guests share practical use cases from the AI Innovation Lab:
  • Talisha Padgett:
    • Brands start with AI pilots in areas like creative, analytics, and support call centers. Analytics and AI-based market research allow safe, incremental exploration.

      “It's been a good place for me to see people's fear subside slightly or their excitement appear.” (10:53)

  • Michelle Boockoff-Bajdek:
    • Cites a global consumer brand’s content localization challenge, where AI was trained with brand guidelines and glossaries, with human oversight:

      “Local teams accepted nearly something like 80% of the AI suggestions unchanged because the AI had truly absorbed and understood the brand voice ... It didn't replace creative judgment, it accelerated it.” (12:12)

5. Measuring Empathy and Trust in AI-Driven Experiences

Timestamps: 12:33–15:38

• How can brands quantify empathy and trust, not just efficiency?
  • Talisha Padgett:

    “For me, I would say continued engagement ... Engagement and actually continuation into that process ... it's really obvious when something doesn't feel human centric.” (13:17)

    • Empathy coaching and testing different journey scenarios are core tactics.
    • Success signals include higher click-through, longer engagement, and voluntary customer actions (e.g., information sharing, referrals).
  • Michelle Boockoff-Bajdek:

    “Those are not necessarily all of the KPIs that marketers have relied on in the past, but I think they're going to be incredibly important ... they show that you're earning belief, not just attention.” (14:55)

6. Ethical & Responsible AI at Scale

Timestamps: 15:38–19:25

• “Responsibility” as the linchpin for future-ready, scalable marketing:
  • Talisha Padgett:
    • Microsoft’s rigorous approach: transparency, informed usage, legal oversight, privacy and compliance, internal and external review boards.

      “Any agent developed within marketing has to go through an impact assessment ... anything that’s customer facing goes through a deployment safety board ... to make sure any, anything that we’re going to put out as Microsoft has really been vetted.” (17:12)

  • Michelle Boockoff-Bajdek:

    “If customers don't trust you with their data, then nothing else matters. … Transparency and consent, they are non negotiable.” (17:49)

    • Sitecore commits not to use customer data in training LLMs, builds provenance and plagiarism checks, and stresses the need to “protect the data, protect the content, protect the relationship.”

7. Most Impactful Actions for Marketing Leaders

Timestamps: 19:54–22:14

• Michelle Boockoff-Bajdek:

  “You have to start building fluency across your teams ... We've made it a priority to help our teams really develop confidence and curiosity. Those are the power skills.” (19:56)

  • Recommends experimentation and knowledge sharing in real working environments to build comfort and capability with AI.
• Talisha Padgett:

  “For anyone that has fear, I think they should get started. They should definitely try using our innovation lab because we know this is where the future is headed.” (21:52)

8. Staying Agile as Leaders

Timestamps: 22:14–23:24

• Talisha Padgett:
  • Stays agile by fostering a collaborative team, sharing insights, experimenting with small pilots.
• Michelle Boockoff-Bajdek:

  “You can't lead from the sidelines, you have to lead from the front ... Leaders need to model curiosity and confidence. ... It's safe to explore, to learn, and frankly, that it's safe to get it wrong.” (22:56)

Notable Quotes

• “Traditional segments told us who the customer was, but signals tell us what they're doing right now.” – Michelle Boockoff-Bajdek (03:44)
• “Technology like Sitecore can clear the noise so we can focus on the moments that matter.” – Michelle Boockoff-Bajdek (05:20)
• “AI is not something that people should be fearful of if used in the correct way.” – Talisha Padgett (06:30)
• “Labs give brands this safe, guided environment to explore before they deploy.” – Michelle Boockoff-Bajdek (09:25)
• “Local teams accepted nearly something like 80% of the AI suggestions unchanged because the AI had truly absorbed and understood the brand voice.” – Michelle Boockoff-Bajdek (12:12)
• “If customers don't trust you with their data, then nothing else matters.” – Michelle Boockoff-Bajdek (17:49)
• “Any agent developed within marketing has to go through an impact assessment ... anything that’s customer facing goes through a deployment safety board.” – Talisha Padgett (17:12)
• “You can't lead from the sidelines, you have to lead from the front.” – Michelle Boockoff-Bajdek (22:56)

Important Segment Timestamps

• Guest Introductions & Roles: 01:50–02:54
• Shifting to Signal-based Marketing: 03:31–04:42
• Designed Intelligence & Amplifying Human Creativity: 04:44–07:04
• Overcoming Enterprise AI Fear & Labs: 07:04–09:51
• Real-world AI Use Case (Localization): 09:53–12:33
• Measuring Empathy & Trust in AI: 12:33–15:38
• Responsible AI & Governance: 15:38–19:25
• Advice for Marketing Leaders: 19:54–22:14
• Staying Agile: 22:14–23:24

Summary & Takeaways

• AI’s real marketing power is in amplifying human creativity and empathy, not just efficiency.
• A fundamental mindset and organizational shift is needed from static customer segments to real-time behavioral signals.
• Pilot programs (“labs”) are invaluable for building confidence and surfacing practical challenges before rolling out AI at scale.
• Transparency, responsibility, and building trust in data use and content provenance are non-negotiable for customer relationships.
• The most impactful action for marketing leaders is building team fluency through experimentation, curiosity, and knowledge sharing.
• Modern leaders must lead from the front, model learning, and make it safe for teams to take risks and grow.

For further insights on these topics, catch Michelle Boockoff-Bajdek and Talisha Padgett at the Sitecore Symposium, Nov 3–5, Orlando, FL.