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The Agile Brand.
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Welcome to Season seven of the Agile Brand where we discuss the trends and topics marketing leaders need to know. Stay curious, stay agile and join the top enterprise brands and martech platforms as we explore marketing technology, AI, E commerce, and whatever's next for the omnichannel customer experience. Together, we'll discover what it takes to create an agile brand built for today and tomorrow and built for customers, employees and continued business growth. I'm your host Greg Kilstrom, advising Fortune 1000 brands on martech, AI and marketing operations. To make sure you always get the latest episodes, please hit subscribe on the app you listen to podcasts on and leave us a rating so others can find us as well. Now onto the show. In the race to adopt AI, how do we avoid creating a sea of sameness and alienating the very customers we're trying to connect with? Today, we're going to talk about the intentional design of our marketing future. We'll explore how leading brands are moving beyond the hype of AI to build practical collaborative frameworks between humans and machines, shifting from outdated customer segments to real time signals, and ultimately creating experiences that are not only efficient, but deeply empathetic and relevant. To help me discuss this topic, I'd like to welcome Michelle Bukoff Beideck, CMO at Sitecore, and Talisha Padgett, GM, MarTech AI and Automation at Microsoft, who will also be doing a fireside chat at the upcoming Sitecore Symposium November 3to5 in Orlando, Florida. We're going to get a sneak preview today of some of the topics they'll be discussing. Michelle and Talisha, welcome to the show.
C
Thank you. Thanks for having us.
A
Yeah, it's great to be here. Yeah.
B
Looking forward to diving in here and getting that preview. Before we dive in though, why don't you both give a little background on yourselves and your roles.
C
Okay, thanks. So, like you mentioned, I'm Talisha Padgett. I've been with Microsoft for three years, but I've spent over 17 of the 23 year career in martech and most notably analytics and now artificial intelligence. And so it was really great for me to see how data technology AI can really enable marketing strategy. And that's what I love to do.
A
I'll go. And Greg, thank you. You pronounced my name perfectly. Michelle Bookof Beideck. Although everybody calls me Michelle BB I have the privilege of serving as the Chief Marketing Officer at sitecore. I won't tell you how many years I've been in marketing, but you know, at its heart, sitecore is here to help brands Reach, engage and serve their customers and to create digital experiences so powerful they connect the world. And you know, that is something that's always resonated with me because I have spent much of my career at the intersection of technology and humanity. So I'm really excited to be here.
B
Nice, nice. Love it. Well, yeah, we're going to cover, cover a few things here today. I want to start with this new strategic imperative of really redefining relevance and intelligence. And so there's this powerful distinction between marketers working in segments and customers living in signals. For an enterprise, shifting from a segment based model that's been in place for years is a monumental task. I certainly know this firsthand. What's the first, you know, most critical step that a marketing leader should take to begin building this signal fluency within their organization?
A
Well, I'll go ahead and kick this one off, Greg. Look, I think frankly that the most critical step is reframing how organizations understand the customer. I think we've always had this view of customer as a sort of static identity and we need to really reframe to dynamic intent. So if you think about it, traditional segments told us who the customer was, but signals tell us what they're doing right now. And I think that is a real mindset shift. It doesn't mean that we abandon our data, by the way. Right. Actually, it means that we have to bring it all together and not just the data that we know about a customer, kind of who they are, but what they're doing. Clicks, searches, social interactions, purchases. We have to be able to bring it all together. And I think those signals are beacons for us. They tell us how to reach our customer wherever they are, in the moments that matter. And so, you know, for when I, when I think about this, it's an opportunity to really leverage technology. But I also think it's a, it's a cultural opportunity because we have really these, these opportunities to break down silos between marketing and sales and product and data teams all aligned around a living, breathing picture of the customer.
C
Yeah, well said.
B
And so, you know, this, this can be framed as, you know, this human AI collaboration can be framed as designed intelligence. So intentional choreography. I think a lot of leaders hear AI and they immediately think that, you know, they think they go purely to automation, maybe they go to cost reduction, you know, the efficiency play, so to speak. How do you reframe the conversation to focus on AI as a tool for accelerating creativity and empathy rather than just that efficiency?
A
I love this concept of designed intelligence because when we talk about it. We're talking about a partnership. It is an intentional choreography, as you said, between human creativity and machine capability. Look, I think too often we do jump straight into automation to scale and cost reduction, but I think the real opportunity is amplification. Using AI to extend human imagination, to extend empathy and design. I like to say that technology like sitecore can clear the noise so we can focus on the moments that matter. And I think that's the essence of design intelligence. 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. And look, I think we should still be looking at and thinking about how AI can make us more efficient. Like I don't want us to take that question off the table, but I also think we need to be asking how can it make us more empathetic? How can it help us design experiences that people will remember?
C
And I couldn't agree more. I mean, I like the point that you made in your previous comment around data and how we need to look at be curious. We're leveraging data to help us create better customers experience. We're trying to understand what they may be going through, where they're getting bad experiences and reframing and rethinking that and using AI to do so. So again, I actually like the idea of designed intelligence. AI is not something that people should be fearful of if used in the correct way. And it really does empower humans to think more about what they would want in an experience, what they would want in their marketing interaction and create new ways of engaging which I think will actually drive us to a more kind of a frontier marketing world where it's actually more better for the customer.
B
Yeah, yeah. And I think, you know, there, there is a lot of pressure to do AI, whatever that means. But you know, from, from leadership, from stakeholders and yet, you know, to, to what you're both saying, there's good ways and there's better ways of doing this and you know, so brings me to the next topic. The sitecore AI Innovation Lab developed with Microsoft is, you know, aim to do a few things, but one of those is to kind of de risk that AI investment. You know, we want to be efficient, but we also want to do some of those other things that you're talking about. So you know, Talisha, maybe start with you. You know, from the Microsoft perspective, what's the most common hesitation or fear you see from enterprise clients regarding generative AI? And how is this lab environment designed to Address that initial uncertainty.
C
It's a great question. I mean, most people that we engage with are just unsure about where to get started. I think a lot of people are hearing so much around AI and they want to do multiple experience at one time. You know, I always recommend you need to be using AI to align to any business strategies or goals. If you are working on an efficiency goal, great. And AI can be perfect. But if you're focusing on customer engagement or creating more stickiness, those are ways that you can leverage AI to help enable, like I said previously, versus completely trying to augment entire process end to end. That may not be the best place to start. So these labs I think really are helping customers understand where could we get started? What is the impact that I'm looking to see? And does AI help me in this point? I always say in my world, even before AI, it was always people, process and technology. All three of those things have to work together. And so when we can actually do a small lab or a small pilot first, you see quickly that sometimes you may need to change the process or even the people's roles that are around that or the roles may change. And so it's not always about the AI that is more enlightening on some of the other things that you may need to change. And so these labs are a great way to get started. Started in a simple way.
A
Yeah. Talisha, I couldn't agree more because I sometimes wonder if it's not about the capability, but it's about control and this concern that you're going to lose it. Like what happens to my data? Can I trust the outputs? Is AI really going to understand my brand voice or is it going to kind of go off the rails? And I think that there is this underlying fear, which is why I think the labs are so valuable, because they give brands this safe, guided environment to explore before they deploy. We're not just saying, you know, hey, good luck. We work alongside and prototype and pressure test and fine tune and I just, I really love that.
C
Yeah, yeah, yeah.
B
So maybe to, to make this tangible, do you mind sharing? Don't have to name company names or anything like that, but you know, share a tangible example of a challenge that a brand brought to the lab. And you know, what was the process of, of exploring a solution and maybe that aha moment when they saw the potential for this human AI collaboration.
C
Yeah, I mean there's a couple areas where people start to experiment. Creative is one. But also support call centers is a really great example. And analytics is also a good Area where people have started to explore, I think what you can recognize from prototyping, let's say I'm an analytics front, right? There is a copious amount of data that's required to get the insight that one may want. And so to Michelle's point, if there is that fear of what is this going to do, what this output going to provide for my organization, especially leveraging my data, right? I mean that's the benefit of a product like co pilot and then to see what it can generate, right? That has been something that has been helpful to have people do in small doses, especially in analytics insights, market research, anything that's got a lot of data and people are really curious as to what you can kind of derive from it. It's been a good place for me to see people's kind of fear subside slightly or their excitement appear. So that's what I would say. Michelle, what about you?
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Yeah, I, you know, when, when I look at the labs and where I've seen or where we've seen some success, we had, I'll give you an example. We had a global consumer brand and they came to Leisha with what you were talking about. So their struggle wasn't sort of this really big amorphous topic. It was, hey, we need to do a better job with content localization. Right. They had brilliant creative teams, but actually translating and adapting campaigns for dozens of markets, it's slow, it's expensive. They had some concerns about AI, that it could compromise tone or cultural nuance. And so with Microsoft, we co designed a prototype using this consumer brands brand guidelines and their regional glossaries. And we had human editors there every step of the way. So it did things like flagging tone mismatches and the system learned over time. And what's really wonderful about it is that when we kind of got through this pilot, local teams accepted nearly something like 80% of the AI suggestions unchanged because it had really, the AI had truly absorbed and understood the brand voice. And I think that's a really big aha moment. It didn't replace creative judgment, it accelerated it.
B
So I want to get back to this, this idea of empathy and even trust with this concept of designed intelligence. Because marketing has always been good at measuring efficiency, things like clicks, conversions, cost per lead, even time spent and things. But designed intelligence calls for the empathy and trust that we talked about a little bit earlier. How do we quantify that? You know, how do we, how do we even start there? And you know, what are some of the leading indicators that an AI assisted Experience is successfully building brand trust rather than, you know, driving some of those important but some of those short term transactions.
C
I mean, for me, I would say continued engagement. I think we've all been, we've experienced an AI generated ad or something in your.
B
Right.
C
You don't even want to continue. Right. So engagement and actually continuation into that process, whatever that defined scenario that we'd like the customer to go through. It's really obvious when something doesn't feel human centric and you know, one thing that you didn't say is that I also have a coach coaching business called empathy coaching, which to me is all about leveraging empathy to help you understand your customer, your partner, your colleague's point of view so that you can find a way to collaborate with AI. As I mentioned before, you have so much insight and data, you can actually test different scenarios. Some people don't always want the same thing. And so for us we're starting to do things in our customer journey that we haven't before. Right. Trying to drive people directly into an experience based on insight that we gathered, changing what their first engagement piece, point of contact would be. And so for me, I think the value of leveraging empathy and trust is one, seeing if you feel getting that response from your customer is that continuation, is it resulting in higher click through longer engagement, ultimately conversion. And that does take some time to see. Most customer journeys, especially on the B2B side is not a quick turnaround. And so we want people to continue doing the next things even if they're, you know, starting to go down a path and they start to explore something else, but they continue learning and pulling more information. That to us is a signal that this, these AI generated engagements are still working.
A
Yeah, I think, I think that is so true. It's, you know, it's the moment when I think a customer chooses to interact with you again, when they share more information, when that exchange is valuable to them or when they recommend sort of the experience to someone else. You know, 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 going forward because they show that you're earning belief, right. Not just attention.
C
Yeah, I definitely think the point around the resharing or the referrals, that's going to be huge. And that also goes to the way that we're changing. Right. We're a lot, spending a lot more time on social media and so there's new ways that we've got to quantify successful interactions.
B
Yeah. Yeah. So sitecore Symposium is coming up soon. When this, when the show airs, it'll be about a week and a half away. And both of you are going to be discussing the design for the future of marketing responsibly at scale. And you know, I want to, I want to maybe double click on that word responsibly because I think that's, that's key. What is the single biggest ethical consideration that marketers should keep front of mind as they scale their AI initiatives?
A
Why don't you, do you want to go ahead to Alisha and then I'll, we're probably going to say the same thing.
C
Probably. I'll, I'll go first and you know, I'd love to hear your perspective from a CMOS lens. You know, my team is also accountable for responsible AI. So I can comment from like what we're doing with our legal team to, you know, ensure. And really anytime we're leveraging AI and putting in front of customer, we, we like to note that, right. There's always some kind of disclaimer so that's being used. But internally we're, we're really looking at the data that's using that we're using to build our models to, to determine when, which data we can use. Clearly we're following, following all the privacy policies, but we also have to look at future policies that are being put in place, discussions from a global country perspective. We're kind of in partnership with our legal team paying attention to legislation that's coming down and also really tying what legislation from AI perspective is along with the privacy changes that are happening. Because when we're talking about models and customer data, we have to make sure we're being 100% compliant. So we've had some changes in our web compliance. We're doing a whole bunch. We have a huge RAI program and so any agent that's developed within marketing department has to go through first an impact assessment. Right. What is the impact on the customer? What is the leverage of understanding of the data, the systems that we're building, all of that. And then anything that's customer facing goes through a deployment safety board, which has our C suite executives on there to make sure any, you know, anything that we're going to put out as Microsoft has really been vetted and we know the data and we know the customer experience and we're really confident before we launch it.
A
Yeah, look, I think it is really, really easy to get excited about personalization, predictive experiences. But if customers don't trust you with their data, then nothing else matters. And so for us, you know, transparency and consent, they are non negotiable. Customers should always know how their data is being used and have the confidence that it is in fact being safeguarded. And look, that's a foundational principle for us. We don't use customer data to train large language models. We have built that commitment into our contracts and our platform design from the start. We've invested heavily in security and governance and we're incredibly proud of that. And that kind of rigor, it's not just, you know, it's not just the thing that you check the box with. I think that it is absolutely fundamental. And marketers should be asking their partners about the level of rigor and security and governance because when you are confident, you can innovate more responsibly. That's part one. So I think the second part for sitecore is that as we embed AI more deeply into our content platform, our focus is going to be on responsible and authentic creation at scale so that every single asset has a verifiable provenance trail. We're building in originality and plagiarism checks. We are strengthening authenticity and factual accuracy through AI assisted verification because, you know, marketers need to move faster, but they also need to know that their content is original, it is factual and it is brand safe. And I think the sort of net of this is if you protect the data, you protect the content, you can protect the relationship.
B
Yeah, love it. Well, as we wrap up here, couple last things here. You know, we've got a lot of marketing leaders that listen to the show. Certainly faced with a lot of priorities and sometimes competing priorities, I know it may be hard to choose just one. But you know, for those that are preparing for this human AI collaboration, the signal based marketing, what would be your recommendation for the single most impactful action they could take today?
A
Well, I'll start here if you don't mind. Look, this may seem basic, but you have to start building fluency across your teams. It is something that we believe passionately. We are a sitecore first and Microsoft shop, which means that everything we do, from strategy to creative to execution, it's got to run on our platform and on Microsoft. It is not theoretical to us. It is built into how we operate and it's not just about the technology. We've made it a priority to help our teams really develop confidence and curiosity. Those are the power skills that I think are so incredibly important through hands on practice. Bring AI into work, test ideas Challenge assumptions and share what you learn with others. Because I think when you know the tech and when you start to become fluent and you aren't as fearful of it, that's when you're actually going to produce better, more human led creative content and development. And I just, look, I think that this is a really exciting time and I think the work that we're doing with Microsoft around the AI Innovation Lab where we are co creating solutions, prototyping ideas, exploring how signals can inform experiences, we are building confidence across marketing teams because they are able to experiment in a really, I think valuable but also way that gives them a little bit of protection and safety so they can, they can stay in control.
C
Yeah, and I would agree, I mean even within Microsoft, we're using our first party products as I'm building bespoke solutions for marketers within our marketing department. We're doing that with Microsoft products and all of our strategic partners like sitecore. So we're not going out and creating a ton of. Net new things that we don't know what the outcome would be. We're working with people that we trust and using our first party products, working very closely with legal but also incredible customers. Right. To gain more and more insight. So I think we're all in this place of learning especially how to transform marketing organization because we know that AI will benefit us. And so 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. Yeah.
B
Love it. Well, Michelle and Talisha, thanks so much for sharing all your insights today. One last question for each of you. What do you do to stay agile in your role and how do you find a way to do it consistently?
C
Well, I have a great team, so I'll say that I have a great team of folks that keep me sharp. We have a chat where we're sharing articles and information. We definitely leverage the information that we have at our doorstep. But we also go out and find out new information. We do small pilots. We have a small testing environment within my organization which I'm really proud of the team that stood that up. So we're doing the same thing. I think as most people are here. Keep reading the sharing the results.
A
Yeah, you know, look, I have learned that you can't lead from the sidelines, you have to lead from the front. So I've jumped in with AI myself and I think it is truly important for leaders to model curiosity and confidence. And my team, you know, like Talisha said, they need to see that it's safe to explore, that it's safe to learn, and frankly, that it's safe to get it wrong. Sometimes I think you earn that trust not when you have all the answers, but when you are willing to actually take the first step.
B
Love it. Well, again, I'd like to thank Michelle Bokoff, Bidoch and Talisha Padgett for joining the show. You can learn more about Michelle, Talisha, sitecore and Microsoft by following the links in the show notes. And of course, don't miss Sitecore Symposium November 3 through 5 in Orlando, Florida. Register today at symposium.sitecore.com thanks again for listening to the Agile Brand. If you enjoyed the show, please take a minute to subscribe and leave us a rating so that others can find the show as well. You can access more episodes of the show@theagile brand.com that's theagile brand.com and contact me. If you're interested in consulting or advisory services or are looking for a speaker for your next event, go to www.greg kilstrom.com that's G R E G K I H L S t r o m.com the Agile brand is produced by Missing Link, a Latina owned, strategy driven, creatively fueled production co op. From ideation to creation, they craft human connections through intelligent, engaging and informative content. Until next time, stay curious and stay agile.
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The Agile Brand.
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Before we continue, I wanted to share a key strategic resource that a majority of the Fortune 500 are already aware of. Finding the best technology, business and talent solutions is not easy. With business demands and competitive pressures mounting, you need to be able to design, deploy, and optimize your technology to provide leading customer experiences while driving business growth. Those of you that have been listening to this show for a while know that this podcast is brought to you by Tech Systems, a global provider of technology, business and talent solutions for more than 80% of the Fortune 500. Tech Systems accelerates business transformation for their customers. Whether you're looking to maximize your technology roi, drive business growth, or elevate customer experiences, Tech Systems enables enterprises to capitalize on change. Learn more@techsystems.com that's teksystems.com now let's get back to the show.
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)
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.
Timestamps: 03:31–04:42
“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)
Timestamps: 04:44–07:04
“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)
“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)
Timestamps: 07:04–09:51
“All three of those things have to work together—people, process, and technology ... these labs are a great way to get started.” (08:40)
“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)
Timestamps: 09:53–12:33
“It's been a good place for me to see people's fear subside slightly or their excitement appear.” (10:53)
“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)
Timestamps: 12:33–15:38
“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)
“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)
Timestamps: 15:38–19:25
“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)
“If customers don't trust you with their data, then nothing else matters. … Transparency and consent, they are non negotiable.” (17:49)
Timestamps: 19:54–22:14
“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)
“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)
Timestamps: 22:14–23:24
“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)
For further insights on these topics, catch Michelle Boockoff-Bajdek and Talisha Padgett at the Sitecore Symposium, Nov 3–5, Orlando, FL.