Twilio's CMO Scrapped His 2026 Plan in One Month

23:04And so my worry is that you create this class of AI-fluent people that are so much more productive, valuable, like they can create their own companies and days and new software and all that. And then you have a whole class of people that are just trying to figure out what AI is. And how do we educate the rest of the population that this stuff is coming and you need to start learning because it's inevitable. And that's going to be a tricky societal problem.

23:37Chris Koehler:Man, that is an interesting world. And I do wonder, I'm like, do they need to know? Does everyone need to know? Everyone said that we all needed to know about NFTs and crypto and blockchain. And I'm pretty sure no one actually needed to know about those things. And the good technology went behind the scenes. Yeah, I mean, it could be a world where they don't know. They don't understand the underlying tech. They just know the new experiences that are created and they can benefit as part of that. That is an interesting dynamic. But I do think there's a world where, and we've even seen it with OpenClaw and some of these others, where you're going to create very small companies that are going to be tremendously valuable.

24:19and the world of these massive, massive companies with hundreds of thousands of employees, like you don't survive in a new world or does the dynamic of there are more entrepreneurs, more smaller companies that are more specialized. I don't know. I think that's a big thing that we're gonna figure out.

24:38Chris Koehler:Yep, yeah, I agree. Yeah, I'm also wondering now, it's getting a little in the details of if I'm a company, let's say Twilio, how do I become the preferred partner? Let's say Claude, where I'm like, I want to incorporate SMS into my app. Like, how do you make sure your company shows up in that? Because right now it's, it tells me to do things. It's like, you should have a clerk and Vercel and this and that. And I'm just like, okay, sure. Send it. Well, it's, it's, it's funny. Like we, I mean, we talk about this every, like every day. And how do you become embedded? Because I think the early, the earlier R pays massive, massive dividends.

25:14And each one of the models is slightly different. and where they take their sort of authority of where they learn from. Some of it might be, you know, your documentation, right? Is your documentation available? And so when they go scan, they're like, oh, this seems to be the leader. I think brand, and we can talk about that in a second, is going to matter around that and part of why we've pivoted to driving more brand. It can be YouTube videos, it can be code snippets, it can be, you know, your website content, the content that you create, but you have to optimize, right? And you have to optimize for that.

25:47And you have to probably have already done it. Because what's happening is that those that were sort of ahead are getting even further ahead because they've put the resources and the approach around that. But it's hard to change because imagine a world where all the different iterations of how you might describe what you want to build, how do you optimize for that? It's not a specific keyword. It's just natural language for you. And so for us as like brands, we're trying to figure out, okay, what is our share of voice? What are those, you know, how do people describe it? What are the problems they're trying to solve?

26:21That's all fun, but it's brand new. Like this is within, I don't say the last 12 months. We didn't have anyone two years ago thinking what's our AEO strategy? Like it's brand new.

26:33Chris Koehler:So let's dive into brand. It's like you're reading my mind. That was my next question. So I was just going to ask if brand even matters anymore, especially as we're entering into this agent-buyer space, not even agent-to-agent, but let's just say an agent coming and looking or an LLM coming and looking and finding the information it needs for its user. Does brand matter? It's a great question and one that I could tell you my head of brand and I had a long, you know, recent discussion around this piece. My short answer is yes, and I'll tell you why. I don't know that it's going to matter so much to an individual agent that's going in and looking for a technical solution around how to solve something.

27:13So I think the notion of how companies do product discovery. Again, that can be a consumer, how they do product discovery, how B2B buyers do product discovery. I think they're going to leverage both the LLMs and agents more than they do today to figure that stuff out for them. And I can imagine a world where maybe I'm a software buyer and I said, hey, I'm looking for a new solution. Go build, prototype, and come back with a recommendation around that. So the buyers or I need a new pair of jeans. I'm not sure what I want. I don't know what brands I want, but this is kind of the style I'm looking for.

27:55You kind of know what I generally like. go find, you know, a pair of jeans for me. When that discovery happens, it's going to come back. And this is where brand matters because I think often in a B2B world is someone to stake a new project on some brand that they've never even heard of. Like when you, you know, when, when it came back to where you like, huh, who's Vercel? Oh, I know Vercel. Of course. Yeah. Yeah. That makes sense. It came back with some company you've never heard of. You're going to be like, I don't know. Let me go figure out, am I going to stake what I'm building on top of that?

28:31So I think brand then rises the awareness and you're like, for us, okay, if I need SMS, yeah, Twilio, of course. If it's some company I've never heard of, do they have the reliability? Do they have the availability? Maybe I should figure that out. Or I'm going to go back and ask the agent, why did you recommend this versus someone else I might know? So I do think there's a world where brands actually might matter even more because the buyers aren't doing the discovery and the research themselves. They're just doing basically the selection and validation now.

29:09Chris Koehler:Yep. Okay. So then that seems like it's a different kind of brand instead of maybe visually seeing a brand and the colors and all that. It's more reading just the company name and then having a memory associated with that company name to be like, ah, Twilio is the one that I'm thinking of. That's the one, which seems like a different kind of brand building. Yeah, I mean, totally, because I think there's a world where as marketers, we've talked about aided and unaided brand awareness, right? It's like when you describe something, who comes to mind? And those are really hard and they're really expensive, right?

29:43Especially for B2B companies, even B2C, when you've got a large market, you have to spend a lot to go drive awareness around that. But I do think that will matter because if you're in a world where an agent is doing the selection or others, maybe the visual identity, it's what you stand for in your voice, your tone, and the attributes may matter, but the visuals may not. But I think we're still a little ways away from that world where, you know, I'm even thinking personally, hey, I want a new marketing automation tool, you know, or I need components of a new marketing automation tool. Go figure out what components I should go, you know, I should go leverage as part of that.

30:22I'm still probably going to do a little bit of my own research based on the recommendations. I think at some point we'll get to where, you know, you'll completely trust the agents to do that on your behalf. But I still think we're pretty far away from that.

30:36Chris Koehler:It's funny because a lot of things that we said we are far away from a couple months ago, I feel like we're here now. That is true. The horizon of how far away might be six months from now. Whereas, you know, I think coming into the year, I was probably like, we have 27, 28, like we've got to address all of that. Now it's like, man, this stuff is iterating so fast that your horizon, like we talked about before, matters. When it comes to all of these new capabilities and all this new data, and we've got non-developers creating things that only developers could make before, how do you think about measuring success in your role now?

31:13Chris Koehler:Like, what does that look like? It's constantly evolving, right? And I think for a long time, there was always this notion as marketers where we had the stuff that we felt really comfortable measuring and the stuff that felt squishy. And when you get to press and media and brand and awareness, all that stuff, there are models you can build. But it is, it's, I would describe it as it was always felt more squishy around that. And then when you got into our, you know, whether for a long time it was direct mail to then you get to digital, you can measure everything. You feel really, really good about being very data driven, very analytical around that.

31:57So you almost had like two parts of it. the, you know, the art and the science, you know, how do you, how do you think through that? I think all of that in all of the measurement frameworks potentially are, are going to change overnight because our media strategy may be very different. You know, there's a world where I have to go build way more content for the agents and, and, you know, the, the models than maybe for humans. And like, how do I measure the success? How do I even know the effectiveness of a piece of content that I created that I don't know if an agent read that or not. There's no visibility around that.

32:35So I think we're going to have to get much more comfortable over the next few years of not fully understanding what's working and what's not, but at a high level, get a sense, is it driving more revenue for the business? And you may not know exactly how the work that you're doing is attributing to it.

32:55Chris Koehler:I love that because it's so truthful. I feel like I've asked this question before. And I mean, to me, that is the truth of where we're at right now is like, you might just not know and you might have to trust your intuition and look at revenue and, and see. But yeah, it does feel like just such a different space now. Yeah, there was a great example with my team about a month ago where the team was like, listen, we have this new idea. You know, it's a crazy idea. We're going to do, we're going to do a pod, we're going to basically a video podcast or webinar around this. And we're going to have a guest who's a human.

33:30And then we're going to create an AI agent who is going to be a guest as part of that. So we're going to ask questions of the human expert and then the AI expert around that. And I was like, wow, this sounds super fun. Like, I love this idea. I was in London and the team was presenting this. And I said, oh, cool. Is this global? No, we're going to test it in Europe. I was like, okay. All right, why?

33:57Chris Koehler:Europe of all places. You're going to get in trouble. And he was like, well, we want to make sure that it works. And I was like, well, how are you measuring whether it works? They're like, well, we might gate the content. I was like, oh my God, guys. Actually, I don't care. they're like, yeah, but we spent a bunch of money on this. And, and, you know, it's relative, but I was like, this is a fun, cool idea that shows our thought leadership. And you guys like are thinking like one step ahead of what I'm seeing a lot in the market. I don't care. Put it out there. See the reaction. You'll know the success of it.

34:32If people are engaged, they're talking about it, they're excited. And this is a hit. If it doesn't, that's fine. Then, then we move on and we try something else. But I think too often in marketers as a whole, we've been very focused on let's measure everything and ensure that the stuff works. And then you get really safe because you only do the stuff that you can measure and you can go justify. But sometimes you just got to take bets and try stuff. And if it works, great. If it doesn't, move on and try something else.

35:05Chris Koehler:So did it work? What happened? We're, we just, it, it's in, it's in process. So, you know, we, we definitely didn't do it just for, you know, for Europe and I got to get a readout from a team around it. But yeah, I mean, I think it's, this is something fun that we're just changing the mindset of marketers to, to go experiment. Yeah. I mean, I told my team the other day, I'm like, Hey, hook up Hey Jen and 11 labs and do what you gotta do and just let a fake me interview Chris and see how it goes. I know we were chatting about this before, but you know, the same thing, like there's these new tools.

35:42It's like, I think eventually we're all going to have these digital twins. And I was playing around with something where I didn't do it. I didn't have, um, I didn't have the time to fully build it out, but I did build a digital twin in HM and I was playing and it's, it's pretty good. Like with not a lot of effort. Um, and I can imagine a world where, you know, I, you know, it gets back into the authenticity. I think that's the thing we're going to go solve is like, what's real and what's not. But I think we will have digital twins at some point that are going to go and listen and record and engage, you know, with whether it's social media or people, you know, face to face or our digital twins could be doing this interview.

36:25And then we just approve the content of like, Hey, that was a great conversation. I was off doing something else, but let's go publish it. That was, that was great.

36:33Chris Koehler:We should totally do that. That'd be so fun. And I would make myself sound even smarter than I already am. Like I would be a genius. It is, um, that's a whole new world. I was, um, I'll tell you something I was thinking about, uh, playing around with today. So we do major, like major events and, and my team was saying, Hey, listen, I was meeting with them last night and they said, hey, we need to start thinking about locking down venues for 2029. I was like, wow. Okay. 2029. What's even happening then? Wow. That was when I was like, are these going to be a thing? And so I was asking my handy AI tools.

37:18And I was like, listen, help me think through what does 2029 look like from an event perspective where we've got agents doing a lot of the buying, what type of experience might I need to create in 2029? And interesting ideas I hadn't fully thought through is you may need to create content for agents that are like their people will send their digital twin or their agent to an event, learn that content, come back and summarize that. So there'll have to be a whole track around content for agents that go back to, you know, summarized for humans. And then you may have an in-person track where people don't want any content.

38:02They just want to build the interconnections and meet with their peers. And it's all about relationship building. It's not about content. And I was like, wow, that's a totally different format than how everyone's doing events now. How should we be thinking about it? Should we be locking into 2029 or does the venues and everything else change in that world? Like, I don't know. So, but it is hard to imagine what this might look like and the types of activities we do today may be very different next year or the following year. But the way that marketing runs today is you have to, you know, you've got to lock in venues three years from now.

38:38Chris Koehler:Yeah. Yeah. Yeah. There's another company I'm running. It's a membership group, mostly for business folks. They've had one, two, three businesses. And they basically said that they don't need speakers to teach them things. They can learn that. They can go on YouTube. They can learn anywhere else. And that they really just want the human connection community, knowing there's a good curation of who's going to be in the room. And I found that so interesting, thinking about all the events that I've been through over the years. And everything's focused on who's the speaker. What am I going to learn?

39:08Chris Koehler:And now it seems like, I mean, I'm very biased. And this is one small example, but it seems like the world is moving to human connection and community and wanting to meet good people. I know it's a great place that's curated to find your people. Yeah. I mean, we're seeing a lot of success. And part of why I'm traveling today is I'm hosting a dinner tonight with both customers, you know, and potential customers with that same notion in mind. We're just bringing together a bunch of really smart people to talk about what's happening in the industry. No, no sales pitch. Just like, hey, what are people, how are people dealing with all of the changes happening in the world?

39:46You meet a few other people that then you can, you know, you can reach out to later and ask questions. Like there's a lot of value in that. Just creating human connection and asking questions, especially in a world that is so uncertain right now that you want to have peers to say, hey, I'm kind of struggling with this. How are you guys dealing with this? That's really, really valuable right now. Yeah.

40:09Chris Koehler:And doesn't it feel like the world's kind of shifting to the more collaboration approach versus, I mean, when I was in the Bay Area, it felt so competitive. No one would share anything. It just felt like a dog eat dog type of world. And now from what I see over this past at least six months to a year, it feels like leaders are coming together and wanting to support and not be as competitive as it at least used to feel to me when I was in your neck of the woods. Yeah. I mean, I think there was a world where there was always a worry like, oh, we can't get people in the same industry together at a dinner or an event.

40:41And the reality is that's not true anymore. They're competitive, but at the same time, they share the same problems that they're dealing with. And so they're more than happy to talk to their peers. They may guard the information that they share, but they still want to know and they want to meet people. And I see it all the time in financial services. You have multiple people that work at banks that are in the same room and they're collaborating on what are you dealing with? How are you dealing with that? And that's fine. I mean, I think that's the world because there is so much change and so much uncertainty.

41:13And there's so much opportunity, I would describe, that I don't think we're thinking about this as it's a zero-sum game.

41:19Chris Koehler:team there's a lot of opportunity for everyone is there anyone that you follow or just mentors or people you don't even know that you're like these are people i like to look and see what they're doing and or have good advice or change the way i'm thinking there's there's a lot right and i told my team um it's overwhelming to keep up with like quite frankly of all the tech innovation that's happening um i think there are a handful of founders that are sort of on the cusp of the technology of like where, where a lot of this is happening. What I told my team, whether you like X or not, and we won't get into that situation, but X is where so much innovation sharing is happening.

42:03And I follow all sorts of people that I don't even know who they are, but I love what they're posting in their content. And I'm like constantly forwarding to my team, hey this is an interesting construct like go listen to this you know 15 minute video around that because I'm like I said a sponge learning learning trying to keep up and it's it's exhausting but it's also like pretty exciting to think about where we're headed.

42:32Chris Koehler:I think I need to have an AI agent scraping Twitter and then knowing my curation filter and then I can put on some people be like what is Chris like who is he forwarding along and just surface me the top five every day so I don't have to look on Twitter. It's a lot of work. I do have a handful of, I would describe, whether they're agents or queries, however you want to think through it, where I do curate content on different topics every day. Who's this for? Why haven't you said it yet? I want this. This is really for me. And then it was funny, I was talking to some of my leaders yesterday. I'm like, maybe I need to share my own personal, like here, here's how I'm consuming it.

43:17But I've got different versions of it. Like one is all about marketing and AI, you know, give me examples of how marketers are actually changing their processes with examples. Like, don't give me that we're going to use AI to change the world. It's like, no, give me real world examples where people have talked about, here's how I leverage this technology. Here's how the workflow changed. This is what we did. So I have every day, like goes out, scrapes and comes back with a summary around that. I've got industry stuff. What's happening in our industry? Give me an update, any competitive info. I've got a bunch of different categories I think through.

43:54I've got that around just AI and technology as a whole. Basically go out, build me an executive summary of the five different subject areas I need to think about. And so my new routine is like, I'll wake up and I'm like, okay, what happened overnight? what happened yesterday that I haven't been able to keep up with. And that's how then I curate that and I say, oh, hey, team, here's pretty interesting. Take a look at this as part of that. And so we're trying to change it as everyone's building their own information filters and models around that. You know, what's the new information sharing that doesn't become like we're spending all of our time just trying to keep up with everything that's going on?

44:33Chris Koehler:So of all of the things that you saw, was there one that stood out of a process or like something that you saw happening that you shared with your team that blew you away? There was one, I can't remember which one it was. Now it, it goes back to our conversation around AI agents and like, are we, is there a world where agents are going to do the majority of buying versus humans? And there was a whole synopsis. There's, there's been, there's a couple of versions of that where you've got the industry analysts all trying to project how fast that's going to happen. So it's like, okay guys, here's some industry data around it, but here's some other thoughts and examples.

45:10And one was a full article of like the implications. If agents start to become the majority of buyer, what do you have to go do? And so I shifted that one today, but I mean, it is, it is really hard. Like I was just, you know, this morning waking up, doing a summary of what Apple announced yesterday, where they're like, they've got a new, you know, a new laptop that you don't have to go buy a Mac mini anymore and you can run it on your laptop. Right. Wow. That was quick. Yeah. I mean, they've, they've just announced that and they announced a, you know, one that was 500 bucks. Right. So that it was more accessible for people.

45:45You, you try to keep up with all the chip stuff that's happening. You know, the, the foundational companies continue to release new capabilities. Every, it seems like every week there's something new that comes out. So it's just, it's, it's a lot of work just to try to stay current, but it's pretty exciting if, if you're, if you can keep up with it.

46:06Chris Koehler:Yeah, man, I just bought a Mac mini. Didn't even know that Apple was releasing a new computer. They did it yesterday, like, you know, as part of it. So yeah. All right. Okay. So I was on Reddit and I want to ask this question because it seems like there's a lot of conversations around CMOs and marketing leaders feeling paralyzed. So for anyone who's kind of feeling paralyzed with all this crazy change that's happening, what would you say to them? Like, what would be the thing that you tell them to do or think about? Yeah, it's, I get the, you know, the angst, you know, that I think we're all feeling.

46:41I would say what we did is we took a step back and we said, yeah, there's a lot of things we could do. But let's map out. And we did a full, I had one of the leaders on my team, he was in this marketing innovation role. And I said, go interview all the leaders and the thought leaders in the organization. And let's map out all the use cases of what we do across marketing today. There were 40, 50, I can't remember the exact number of like use cases of how we operate today. And let's build a quadrant around this of what are the biggest impact? Where's the level of effort? And where does technology sort of support us in being able to disrupt how we do that today?

47:30And so we built a quadrant and we said, okay, everything in the top right, that's what we're going to focus on first. because I think if you go and you're like, I need to change everything, it's impossible. And then quite frankly, you're not going to get your team on board because it's just going to be too overwhelming and people are going to be like, I can't absorb this. So I'm just going to do it the way that I've always done it. So map that out and really spend some time. And we're continuing to do this. I've got an upcoming leadership offsite where we're going to continue to map out how do we run certain processes in the organization and not everyone has the same, maybe it's like opinion of how those things run.

48:13A global team in APJ or in Europe might have a very different perspective of how things operate versus someone in the United States around how we create and how we run marketing programs around that. So get everyone on the same page. And I think we mentioned it before at the beginning, reimagine what that could look like and don't get enamored by the technology. Figure out the problem we're trying to solve. Let technology go support that. I think that's one of the things I see a lot. I talk to a lot of my peers around this is it gets really easy to focus on the tools, not the actual process and the customer problems we're trying to solve.

48:54So I think if you focus there and the tools enable that, that helps a lot as well.

48:58Chris Koehler:Solid advice. I like it. Okay, Chris, we're going to shift into the lightning round. This is where I ask you a question and you have a minute or so to answer. Are you ready? I am ready. Okay. What is a trend that you're genuinely betting on that has nothing to do with AI? A trend that has nothing to do with AI. My gosh, I don't know any trends outside of AI. I'm stumping all my guests with this one. It's like all we're talking about today. I'm betting on that people are going to crave more human connections in the future than what they have today. And I think you're going to curating more non-tech experiences comes back again.

49:48Chris Koehler:Yes, I thousand percent agree with you there. What is either a book or a podcast that everyone should be reading or listening into? One of my favorites is the Acquired Podcast by Ben and Dave. Super fun. It's long form, right? We know like sometimes it's three plus hours, but you get into the details of how companies are built and all of that that just provide you almost like a mini MBA in every episode that I think it'll make the listeners more well-rounded thinking about how do I run a business versus like my function and where I play and all of that. So I'd say probably, I love that podcast, probably one of my favorites.

50:31Chris Koehler:Yep. I do. I love that one. What is something outside of work that's made you better at your job? Probably my family, you know, supporting my crazy lifestyle of, you know, being able to do this job. But I think we're a couple of things, maybe we're very, very active that allows me to sort of take my mind off the craziness of work. And we love to hike and bike and ski and do all of those things that allow me to disconnect from the all consuming topics that we're dealing with today and allow me to come back when I'm back in it, feeling refreshed and relaxed. I love it. And do you have kids? Yes, two kids, 19 and 15.

51:16Chris Koehler:So I'm in the fun teenage years. Yes, okay. I'm so far from that. My kids are six, six, eight, eight. So you'll have to give me your playbook when I get there. I don't think there is a playbook. You just kind of adjust as you go. Yeah. Just get bumped around and look up. Yep, I'm still alive. Okay. All right. And the last and like the biggest question of this entire list. So you made a bet of things that were in and out in 2026. Do you still believe that bucket hats are in? I don't think they were ever in. They will still be out 100%. Okay. Well, thank you, Chris, for coming on Marketing Trends.

51:55Chris Koehler:I really loved having you. Where can people find out more about you and what you're up to? Yeah, you could check out Twilio.com. That's where we've got a lot of fun. You can follow me on LinkedIn. that's mostly where I post content. We're trying to have fun and be differentiated. And, you know, let's work. Work shouldn't be so serious. We're all, you know, we want to all have fun. I agree.