In the first of our interview series exploring AI and its impacts on leaders across functions, Heidrick & Struggles’ Lindsay Leach and Hugh Marshall were joined by Chris Koehler, the chief marketing officer at Twilio, a customer engagement platform that drives real-time personalized experiences for leading brands. Chris discusses the ways in which his marketing function is using AI and where they are finding it adding particular value, as well as how he uses AI tools in his day-to-day work. The three also discuss what skills and mindsets marketing leaders will need to thrive in this AI-driven world, as well as how they will continue to find talent to make the most of AI.

Below is a full transcript of the episode, which has been lightly edited for clarity.

Welcome to The Heidrick & Struggles Leadership Podcast. Heidrick is the premier global provider of diversified solutions across senior-level executive search, leadership, assessment and development, team and organizational effectiveness, and culture shaping. Every day, we speak with leaders around the world about how they're meeting rising expectations and managing through volatile times, thinking about individual leaders, teams, organizations, and society. Thank you for joining the conversation.

Hugh Marshall: Hi, I'm Hugh Marshall, a partner in Heidrick & Struggles' San Francisco office, and a member of the Global Technology and Services practice. This interview is one in an ongoing series exploring AI and its impacts on leaders across functions: how they are embedding AI tools into their teams, how they are managing its use to drive performance, and how they are adapting their leadership skills and capabilities to best address the challenges AI presents and sees its opportunities

And I'm also joined by my colleague Lindsay Leach.

Lindsay Leach: Thanks, Hugh. Hi, I'm Lindsay Leach, a partner in Heidrick & Struggles' Boston office and a member of the Global Technology Practice. And today we're joined by Chris Koehler, the chief marketing officer of Twilio, a customer engagement platform that drives real-time personalized experiences for today's leading brands.

Prior to joining Twilio, Chris served as CMO at Box, where he helped lead the company to surpass $1 billion in annual revenue in fiscal 2024. Chris has spent more than 25 years leading marketing, customer success solution consulting, demand generation enablement teams at Adobe, E-Trade, SunTrust, and Claritas.

Today, he joins us to talk about artificial intelligence and the marketing function, how they're using it, its challenges and opportunities, and what leaders need to know about how to make the best of it. Chris, welcome, and thank you for taking the time to chat with us today. 

Chris Koehler: Yeah, thank you, Lindsay. Thank you, Hugh. I really appreciate the time today.

Hugh Marshall: Perfect. Well, Chris, to kick us off, how widely is your function using AI and your company, and in what ways in particular have you found it adding value?

Chris Koehler: Oh, man. How much time do we have to get through all of this? It's not as widely as I would like, maybe, is the first way to preface that, but I think as an organization, we're doing a pretty good job across the entire customer experience—in everywhere from like, Hey, someone is hitting our website, how do we personalize that? to they, you know, they raise their hand, they've got intent, and I can talk about details to the customer service experience, to creating code, to driving better analytics in the organization. Every part of the org is really thinking about how do we leverage AI capabilities to drive more efficiency and better output as a company.

I think specifically within the marketing organization, we think about it in probably many different ways. How do we think through customer acquisition? What's our lead gen qualification and nurturing? We actually handle 90% of our inbound inquiries and leads through an agent we call “Isa” that is nurturing and engaging with customers, really trying to understand what's the intent, ultimately, what's the business problem we're trying to solve, and whether that is through our self-service experience, or we cultivate that and we push that off to our sales team. So really exciting developments. And again, every week we're seeing updates. There's such huge potential. As part of this, we're leveraging AI in, you know, obviously the deliverability, our email, our websites. We're delivering, even using our own tools—like Twilio Segment is a CDP platform. How do we think leveraging AI to generate audiences? How do we segment the right people as we're thinking through that? So all around what's the right person, the right time, and the right message? All around acquisition.

We're using it for content creation. Much like you hear, this is sort of probably one of the first places where marketers specifically started—SEO has completely changed and you know how we adapt to that. Copywriting or content around blogs or PR and documentation—we're all leveraging this as an assistant, as we think through that. Social, right? How is it helping us create social posts as part of that? And I can tell you some fun personal examples around that.

And then you get into the visual content—video and imagery and all that—and how we're using tools to create that. So again, we're embracing it across the organization, but it's still very, very early in nascent, I would describe. But the upside and potential is amazing.

Lindsay Leach: It's amazing to see how it's evolved in just such a short period of time, and I think, in the next 12 months, it'll be interesting to see where we get with using AI across, even more throughout an organization.

Curious, Chris, as you think about, you mentioned you have some personal stories, but personally, how do you use AI tools just to be able to do your day-to-day work, and in what capacity do you do that?

Chris Koehler: What's interesting is it's almost becoming the default starting point. Whether that is, Hey, I've got a question around the market or competitive set. Obviously we've got teams that are building that, but it's really interesting for real time, right? So I go into an LLM and, Hey, I've got a question about X, Y, and Z, and it's almost the default, whether that is, you know, perplexity or Google or OpenAI. You know, I mean, again, there's so much interesting capabilities that are happening.

I don't start from a blank screen when I've gotta create something, right? It is the starting point. There's no more notion of a blank page—whether that is an important email that I've got a right to my team to communicate some big program we're working through or in even responses saying, Hey, help me with the tone of this. I want to make sure it's coming across as collaborative or direct or those sort of things.

This week I actually had a fun social post. I was in ChatGPT, and someone had asked me a question early in the week saying, Hey, what are some of the clichés in business that you would like to kill? And so I was like, oh, this is actually a really interesting question. So I opened up ChatGPT, and I said, Hey, help me understand what are the common clichés in business and create a social post out of it. I mean, that took me five seconds to do, and the post now, as of this morning, has 50,000 views or something crazy.

And I think it's just like, how do you leverage this in a fun, creative way? And I think marketers need to embrace it, for sure.

Hugh Marshall: Chris, you've started to touch on this even with the way that you are using it, but can you share with us, and it might not be a blanket way, but how AI has been rolled out in your function? Who led the charge? Was it the CMO? Was it the VPs? Is it the directors? Any challenges that have surprised you? Any cultural pushback or changes that you found? 

Chris Koehler: Oh man, there's so much to this question. I think, you know, and again, if we think about it, we've been using AI for many, many years in marketing, right? And a lot of it was obviously machine learning, and that's been around for years and years and years. I think the notion of generative AI in the last probably two or three years—you know, I can even go back to my time at Box is, as we start to think through, Hey, this is pretty interesting. I think there's more that we could be doing with this.

And I think it was almost like organically in the organization. People started using it in their personal lives, and then they said, Okay, how do I bring this into the workplace? And as tools got more and more capabilities and they got much more valuable, marketers and CMOs have said, Wait, how do I harness this across the organization? Should I be thinking about creating some structure around this? For one, for privacy purposes, right? And you know, security purposes. I think that was the initial push saying, Wait, hopefully we're not putting IP and other confidential information in these public LLMs. So we probably should take a step back and really decide, okay, how should we be using this?

As I talk to a lot of my peers, I think it has been more organic. But it has to come top down. And I think what we're starting to see is—we have an AI council that we've kicked off recently, where I was guilty of this, where I said, Hey, I think there's a massive opportunity for AI in marketing. Everyone should use it.

And you know, my team's like, Okay, well, some of us are. What do you mean? What are the use cases? So I think you have to be much more deliberate around it. And there's new tools popping up literally every day. So what's the structure we put in place to say, Here are the approved tools. This is what's gone through security and compliance and privacy without slowing down because marketers are pushing incredibly fast, and my team is doing this to leverage the new capabilities that are out there. So I think what I've learned is you've got to put structure, you've got to actually drive it at a use-case level. What are we going to go use? What tools are approved? What processes should we be changing as we go through it?

There's this natural fear that, Hey, is AI going to replace my role? And the way that I've talked to my team quite a bit about it is that we have a backlog of things that we want to do. There's more requests that have come in across the marketing organization to create more content and more messaging and additional campaigns. We can't get to it. We don't have enough capacity as part of that. So, if we can leverage AI to create higher quality, better output, and drive more efficiency, that's great. That's the part of the org that I really want to go after. So, rather than thinking about this as a replacement, think about it as an enhancement that's going to allow us to do better work.

Lindsay Leach: Makes sense. And as you think about AI, I am curious how it's kind of transforming the way marketing operates at Twilio or even at Box. If you think of strategy all the way to execution, how is it impacting how you as a leader operate within Twilio?

Chris Koehler: I think because it's rapidly evolving every week, that as a leader, I feel like, and, and I've talked to a lot of other CMOs, we're all feeling behind. We're all feeling like we're not doing enough. You know, we could be doing more and more. I think the way that we operate and run our teams is going to change because the pace at which we can produce content, personalize the experiences for our customers—the clock speed is much different. Where today, where we might go say, Hey, let's go build a campaign. Let's, this is going to take multiple months. We're going to work with our agency. We're going to have back and forth and debate around this, and hey, we hope to get something new in market in the next three to four months. What happens when we can get that out in weeks? All of our, the way that our cadence with the business changes completely.

So we have to be much more, I would say, agile in our approach. And you know, one of the things that I'm building into the culture is test and learn, right? How do we test and learn, test and learn, test and learn. So that we can react very, very quickly. 

So I think as leaders, one, keeping up with the pace of change and being open to continuous learning is like a big one. I think the clock speed changes a lot too. The way that we've operated the business before is just too slow. We have to think through and empower our teams to make decisions very, very quickly, and I think we're just going to end up getting better at our craft as marketers, because this is really changing the way that we work completely.

Hugh Marshall: And Chris, just to build out from that, what skills and mindsets then do you believe leaders will need to thrive in this AI-driven world?

Chris Koehler: If you think about sort of the fixed vs. risk growth mindset, I mean, obviously, we have to have a growth mindset. The way that we did things even two years ago are different than they are today.

So I think the things that are really going to help are those that are inquisitive, that embrace this, I would almost say, like, change in human behavior where we have to go play with the technology much more than I think in the past. And what I've really learned is this notion of, whether it's prompt engineering or testing, like you have to be almost, like, embedded in it every day to think about the just amazing possibilities that are coming out.

So having, like, unlearn the way that we've done this—my wife's psychologist, she has often talks about this notion of how do we unlearn. How do we unlearn the way that we've done marketing for the last 20 to 30 years and do it in a new way? That's change management, that's human behavior. There's a lot of inertia as marketers around how we've done things. So I think this willingness to sort of unlearn what we've done and embrace this new reality, I think that's the people that are going to thrive the most in this new world.

Lindsay Leach: As you look ahead, clearly you're using a bunch of these AI driven tools and innovations, but I'm curious, what do you have your eye on? What do you see as potential future disruptors coming in the near future?

Chris Koehler: I mean, yeah, and it's happening today. Like one of the really interesting things is we're monitoring, as a team, is we're now seeing about 2.5% of our traffic come directly from the LLMs. It doesn't seem like a lot, but the conversion rate is three to four times higher when they come from these LLMs.

So I think in a world as a marketer—what happens when buyers actually have agents? In a world where we're not creating content for people, we're creating content for the agents of the people that we're trying to engage with. What is the purpose of our website? In a future, in a agentic world, where it's not a human coming in and navigating a website, but it's really an agent on behalf of someone else.

Like that's a crazy paradigm that we haven't even thought about. And you know, the conversations we're having as a team quite a bit. If we think about Twilio and how we're supporting, the really cool piece is we're working with our customers, whether that's through our APIs or embedded into their product specifically, how do they drive customer engagement in a very different way? And I think there's a little bit of skepticism today around, hey, customer experience that is AI driven, is that really the future that we want? I think that's the future where we're headed. And content and data and channels are really where we see this massive differentiation for us.

So the contextual data tied back in with the communications channel, like that's where we're trying to play and solve. And I think there's a massive opportunity. And we're seeing now a lot of these AI startups build on top of us because the way that we interact with customers, at least in the short term, is going to change completely. And then what happens when we're in a fully agentic world? I think, as marketers, I don't know how that's even going to play out, but we've gotta think about that 'cause it's not as far away as we think. 

Hugh Marshall: And Chris, if we shift slightly to talent just for a moment here, where is Twilio finding the talent you need to expand and embed your use of AI, and how confident are you that you'll have the talent you need within your function? 

Chris Koehler: I think we're still in the early days where I was actually talking to my son who's working on his master's degree, and he's got an internship all around leveraging generative AI for the intelligence community and capturing content that's out there. And I think we're in a world where the talent isn't fully thinking, I am an AI native, I'm an expert in this, here's my experience across it. But I think we're going to get there fairly quickly. I don't think if, you know, I think about the talent we're working through and how we bring new leaders and other marketers on board. We're not saying fully yet, How much have you embraced AI? How much do you really—you know, give us examples around that.

I think we're very close as we start to think through this, where I think there will be a world where people will have, Here are the capabilities, here's the examples of how I've leveraged AI to drive more efficiency or better output as a business. But I think there's still a reluctance. There's still a little bit of stigma saying, well, you know, is this really my original work?

Is this basically discounting the work that I've done? I think that stigma will go away and people will start to embrace it and say like, Hey, this is what I've done. This is success I've had with AI, and tout that, and those are the individuals that I think we're going to be like, Wow, I want to go get them on my team because I want to take that and bring it into my organization.

So we're not fully there yet, but I think we're pretty close is my sense. 

Hugh Marshall: And then even within the business, have you had to develop new leadership roles to manage the use of AI across the organization? And then how have you done that within marketing specifically?

Chris Koehler: Yeah. It's a big conversation we're having at a leadership level around: how do we coordinate the capabilities of AI across the organization? Like, for instance, if you think about the partnership between sales and marketing, we're doing a lot of work around a rebrand and our voice and how we speak to customers and how we talk about ourselves. Well, how do we take that and all the goodness that marketing's doing and share that with our sales team as they do outreaches to their customers as part of that? What about when someone calls in from a customer experience perspective? So we've got an AI council within marketing, but we also have an AI council within the company, and we've got representation across the different functions there. So I think right now it's a more distributed capability across the org as each function is trying to figure out: how do I leverage AI within my own purview?

But I do think, you know, there's a world where you're going to have to have, right? Whether that's a team or a leader that's like, Hey, I'm sitting on top of this. I'm making sure that we're driving a cohesive AI strategy across the business for sure. Within marketing. I think there may be a world where I've got someone who's ultimately just responsible for driving AI capabilities within the marketing work. We don't have it today. Again, shared responsibility. We've got a council on that front. But I do think there could be a world, you know, in the near future, where we actually have that as a specific role.

Lindsay Leach: Chris, as we reflect on kind of the CMO role within technology companies over the past decade, that's obviously evolved and shifted into more of a technology and data-led function. How do you think the CMO role has really changed now that that is the case, that the expectation around marketing executives is being much more technology-led?

Chris Koehler: Yeah, I mean, I think as a discipline—one, I always say it's a really horizontal discipline because we've got everything from like PR all the way down to data analytics and decision science. And that's a lot to navigate right within the organization and a lot of context switching. But I think even within the last 15 years, like I think we were well equipped as we started to see the digital marketing be a much bigger driver in the analytics. And you know, I was a proponent of this. I spent 10-plus years at Adobe where we really pushed on this notion of the art and science of marketing.

You started to see CMOs get more and more technical over the last 10, 15-plus years, regardless. But I think in this world where we now have to be both creative and technical and analytical is really pushing us, I think to, again, it goes back to that growth mindset. Are we leaning in, learning, right? What's happening? And how do we keep up with all of this is a challenge, right? And I think hiring the right people in the organization that we can lean on is critically important.

Lindsay Leach: I'm curious, Chris, as you reflect on kind of the market, what companies do you think are using AI-driven tools and innovations well?

Chris Koehler: That's a good question. I don't have any that I'm like, Oh my gosh, they're doing it so well. But I think, you know, I don't give Twilio and ourselves enough credit because I think we are doing some interesting stuff—tools that we're engaged, or brands that we're working with. I mean, obviously, from a design perspective what you're seeing both Canva, both from a product perspective and how they're leveraging their own tools. Adobe's doing that as well. That I think is pretty interesting. 

I think there's like a next generation of these new AI-driven companies that are really doing some interesting stuff. Like one customer, which I thought was really just this company called Paradox.AI, and they're really driving and changing with their customers how job applicants leverage their technology and get jobs. So they work with someone like a McDonald's, where, how do I hire someone—something that might have taken a week or longer to hire a new employee—can do it via text in an hour. And I don't know if that's the exact number, but you know how you think through that. So there's like this new emerging way that our customers are engaging with their customers in a very, very different way that I think is pretty exciting.

Hugh Marshall: Chris, within marketing, when we think about the various avenues that a CMO can come up through and the functions that fall under your remit today, which of those is being the most disrupted by AI right now? 

Chris Koehler: Man, I would say it's twofold. I'd say one is acquisition, and how we think through acquiring new customers and that the wave of—like for us, like what's really interesting is we're seeing this avenue new, whether you hear vibe, coding or new platforms, you know, like Cursor, where people are creating applications and leveraging our technology in a completely different way.

It's like making us rethink my growth and acquisition team in a totally different way around how you reach customers—that it may not just be through digital marketing. They come to our website, they sign up, and we drive that. So that's like a massive transformation. I think that's one. And then I think brand and creative is the next. I think those two, my two leaders are probably the ones that I'm pushing the most on this run around. How are we keeping up? What are the new capabilities? So I would say sort of growth and demand and creative and brand are probably the two that are being absolutely disrupted right now, although all of them probably are.

Hugh Marshall: Makes sense. What about a piece of advice that you'd have for other marketing leaders to make the most out of AI? 

Chris Koehler: Use it personally, continuously, because I think what's fascinating is you, it just becomes part of your daily activity. New ideas come up and spark constantly, where I'm like, Hey, I'm doing, wait—I was giving an example around the social post. I was like, wait, I was asking this question to answer something for another podcast, like, couldn't I turn this into a fun social post? And in two seconds I said, I've created that. So I think if you are not hands-on leveraging it, keeping up to speed with everything that's going on, you're going to fall behind.

And so I would say embrace it. It's not going away. It's going to change everything we're doing, but it's pretty exciting.

Lindsay Leach: Chris, one thing I've been thinking about as hearing you talk, has expectations around your role as CMO changed because of the use of AI among, you know, from your peers, or you're curious to get your thoughts on that?

Chris Koehler: Yeah, I mean, I think, in B2B companies, I think marketing has not always been seen as sort of a growth driver of the business. One of the things that it's clear is marketing is well positioned to help drive growth, partner with the sales team, and to be able to create better experiences for our customers, right? Leveraging data, leveraging ways to outreach. So I do think there's this expectation that marketing is stepping up, taking a bigger, broader responsibility in the organizations.

One of the things—and I've been talking about this internally and externally as well—is I think we're going to get to a, a question from our CFOs around, okay, marketing seems ripe for disruption. You guys are investing a lot in new tools and capabilities, but where's the efficiency, right? One of the things that as marketers, we have to do a much better job is highlighting how we're leveraging AI to drive growth for the business, not just how we're leveraging AI to drive efficiency in our marketing spend in our production.

So I think that's the next frontier where a lot of marketers really need to think about how they tell their own story and leverage AI for growth in the business. And that's what I'm doing with our CFO.

Lindsay Leach: Awesome. Thanks for all these insights, Chris. We really appreciate you taking the time, sharing your thoughts with us. Super helpful and appreciate the partnership.

Chris Koehler: Yeah, likewise. This is fun.

Hugh Marshall: Thank you, Chris.

Thanks for listening to The Heidrick & Struggles Leadership Podcast. To make sure you don't miss the next conversation, please subscribe to our channel on your preferred podcast app. And if you're listening via LinkedIn or YouTube, why not share this with your connections? Until next time.

About the interviewers

Lindsay Leach (lleach@heidrick.com) is a partner in Heidrick & Struggles’ Boston office and a member of the global Technology & Services Practice.

Hugh Marshall (hmarshall@heidrick.com) is a partner in the San Francisco office and a member of the global Technology & Services Practice.