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Twilio's CMO Scrapped His 2026 Plan in One Month
00:52:22
What happens when your next customer isn't even human?
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- [00:00]
A
You came into this year with a full strategy mapped out. How long did it last before you had to start rethinking all of that?
- [00:07]
B
It was probably a month ago when the first iteration of OpenClaw came out. I saw something on X and my mind was blown up.
- [00:17]
A
In February 2026, a lot of headlines suddenly started appearing about this new AI
- [00:22]
B
thing called OpenClaw, the AI that actually does things. I didn't even realize what the heck it was. This is much more interesting than using ChatG. And here OpenClaw comes in and destroys everybody.
- [00:35]
A
Chris Koehler is the CMO of Twilio, one of the top customer engagement platforms that's doing over $5 billion in revenue. Chris has been through more marketing transformations than most people will see in an entire career. From helping build the analytics engine at Adobe to leading brand at Box, to now staring down a future where his next customer might not even be a human being.
- [00:55]
B
What if this world where instead of me going and trying to find a product or information, what if I just have my agent do it on my behalf?
- [01:08]
A
For a long time I have heard many different C suite folks saying, you know, we need to have the CTO partnering with the CMO and all these different orgs need to collaborate closer. And I'm pretty sure we just got forced into that reality now because of all this. And it feels like a fun and interesting future we're entering into where it was a lot of talk of having to do this and some companies were doing it, but I still think a lot were not partnering closely with their tech department. And now it's like a forcing function where you have to know them and probably get their support. So you're not just committing bad things into code that you don't know what it is.
- [01:44]
B
Yeah, and I think there's like, there's this interesting, like, where do you build it into your product that goes into production versus where are you using it internally to run and change your business processes? And like, there's obviously we've got our engineering organization that's thinking through how do we embed this. And then we've got our, know, our enterprise technology organization that's saying, here are the tools that you could use that are approved. And I think, I think what's interesting is the rapid iteration of all of these new tools. It's hard to keep up. I mean, look at Anthropic just over the last couple weeks where they're releasing new products. It seems like every other day OpenAI is doing the same thing and you have to feel for the IT organizations where they're like, listen, we're trying to protect the assets and security and vulnerabilities as the business. And you have the business saying, hey, we need access to this now. Like, give it to us. We're falling behind. So there's this, this healthy tension, you know, that we're dealing with right now, just trying to keep up.
- [02:45]
A
So what does that, what does the planning cycle look like for you and your team? I know last time we spoke you talked about these agile sprints, four to six weeks sprints. I mean, what, what does this look like in your world right now, knowing that you are at a massive company and yeah, I'm just curious, like, I want to get a peek inside your team.
- [03:02]
B
Yeah. I mean, again, my team would argue my impatience is tiring probably around this. But I do think there's a world where the larger you get, you sort of think in quarters. Right. And One of my VPs was at an event last week or two weeks ago, and she was talking to some of the AI, foundational AI model companies and their time horizon changes to days and weeks. So as a larger organization, I mean, we're 5 billion in revenue. Like, we've got a, you know, a very large customer base around that. If we think about quarterly to yearly plans, we're going to fall behind for companies that are thinking about weekly, you know, weekly delivery of new products and new capabilities and new commits. So the mindset has to shift. And so, but that's a lot of change management in an organization where the whole process of the company is built around quarters. Especially if you're a public company where you've got a quarterly cadence around earnings, you sort of have run on that quarterly basis, shifting everyone into this new mindset that says, hey, we got to be thinking about this in weeks and months and a month, not, you know, three to four to six weeks or six months away. So it is, we're, it takes time, but we're changing the mindset in a sense of urgency that's very different than what we're used to running.
- [04:32]
A
So does this look like new, just team meetings where you all are discussing the projects, or what does it look like, you know, at a practical level?
- [04:40]
B
One of the things that we're, we're trying to do one is we all have probably too many meetings, you know, than we ultimately can, that we'd all like. But how do you embrace asynchronous work more as well? Because what's really interesting is our ability and output with AI is sort of endless. And I think this is the thing, like we're moving to a new world where you will have AI agents and we can go down that whole path where they're not sleeping, they're working overnight. You're running stuff, you know, you're running queries as part of that. So how do you get to a world where the synchronous meetings are talking about the strategy and the output in the discussion, the deep discussion piece of it not doing readouts and other things where that's typically what we've done? So I think we're, we're trying to figure this out, like full disclosure of what does the new cadence look like. But I think we'll get into a world where we should. We will end up having a lot more asynchronous reading and content creation before we get into the meetings. The meetings are about, you know, the strategy and the discussion and like the piece that you can't necessarily replicate asynchronously. And then you go off and the work get more of the work gets done, you know, asynchronously than it does today.
- [05:54]
A
Yeah, it definitely seems like rethinking the entire everything when I see what can happen now. I mean, thinking about going to sleep and knowing you've got an AI agent working and that it can be AB testing and doing all these things and you can wake up and approve it to continue with iterations and have a full report. It just. With a few of the things that I've seen, I'm like, it feels like everything has to be thought about from a different way now because we built these companies and structures based off, I mean, industrial revolution in a way, going all the way back to. That's like we built systems, you know, for a reason. And now it just seems like everything feels different and. Yeah, a whole new world slightly terrifying and exciting. It depends.
- [06:37]
B
Yeah, it's. And again, I'm trying to, you know, it's easy to get into the terrifying world of oh my gosh, you know, it's a zero sum game. We're all going to be out of jobs as part of that. Like that's, that's natural as humans to go to that, you know, to go to that place. But I don't think we're in a fixed pie scenario where I do think the stuff that we can now leverage with AI is beyond anything we've even thought because there's, there's sort of natural constraints around productivity and cost and those things. So it is, I think the model's going to have to change. I think there's massive opportunity as long as we sort of embrace it and get excited about it, versus everyone focused on the doomsday scenario situation as well.
- [07:23]
A
So when my Claude bot was looking through your LinkedIn and I think it found that you said something around, you need to like, we need to unlearn 20 to 30 years of marketing. It was either on your LinkedIn or it was in one of the comments. And I would love to hear, other than the whole AI agent thing, which we will dive in deeper into that. That'll be a whole piece of this interview. But what other pieces are you thinking about when it comes to unlearning marketing that you still hear, you know, peers quoting and you're like, that doesn't matter anymore.
- [07:53]
B
Maybe everything, you know, and the content that we create, the processes that we run, the structures that we have. If you think about, you know, the notion of marketing for the last 20, 30, 50 years, there is a creative process that we run that I would describe as it's very conveyor belt. We've talked about this for a long time. We've got an idea that we've got to go figure out what's the right Persona and ICP around that. Let's do the creative brief and okay, we're going to create that creative brief. How are we going to position it? What's the competitive impact? Okay, great. Let's go build different creative iterations of this and then we do the copy and then we create the media plan around it. And that takes weeks or months. And this is why I think for so long as marketers, we've talked about this notion of, like, oh, their nirvana of personalization, which we've never really been able to get to. And so if you think about the new modern world, and I was playing around with one of the models today where I had an idea and I was like, hey, I want what I just described. Help me build the full plan of what that could look like. Help me brainstorm around that. And it took me a half hour with fun ideas and all that. My team will probably like, oh, gosh, this is crap. It's part of it. But I think it gets to a point where you can do some ideation and having some fun creative discovery around it. It's not going to be 100% of what we would ship, but it circumvents weeks of discussions around these things. So I think everything that we think about, who we sell to, the content that we create, the formats that we need the processes that we run, the org structures that we have. I think that's all going to change and it's happening sooner than we think. And I think those that embrace that and figure out, okay, how do we change the way that we run marketing are the ones that are going to succeed versus the ones that are going to sort of the way I often describe it is we use AI to drive more efficiency in the crappy processes we run today versus using AI to rethink how we do marketing as a whole. And I think that's the piece where we all have to pivot.
- [10:18]
A
That's good. I feel like that's going to be a quote card right there because yeah, you hear of a lot of companies who are making these automations and adding AI into their their process versus rethinking the whole process. And that's probably, especially in the bigger companies, why these AI projects haven't really been working because they're just automating little pieces of it and then they don't have anyone who really understands how it plays, you know, a bigger part to the whole company. And then it just dies when one thing breaks because they just like set up 100%.
- [10:47]
B
Yeah, we could make a very inefficient process slightly more efficient. But is that the right thing to do or is it reimagine how we might do this in a completely different way?
- [10:57]
A
Yeah, when thinking about reimagining, I mean, I'm wondering what the future tech stack of a marketer is going to look like going forward because it seems like, I mean we've had all these tools. I'll just take myself for example. We used at Mission Go high level for a while and that was how we did a lot of the lead management and landing pages, all these things. And then I just saw we could rebuild that software in a day of what we needed. Like we only need these 10 pieces to it and so then we don't really need that software anymore. And I wonder how much smaller the tech stack for these marketers will be as people realize you can probably build what you want really quickly. What do you think about that?
- [11:38]
B
I think it depends on the size of the org and how long that will take. But I do think we're getting to a world where composability actually will matter more and more. I think with the capabilities it will have. I think there was a, there was a great video from Patrick Collison from Stripe, CEO, founder of Stripe, talking about what was his example. Today most applications are like frozen Food, selling frozen food, where they've been created, they're frozen and they're sold at a later time. That's how a lot of software has been developed. And he said, we're going to move to a world where it's more pizza, where you go in an order and we, you know, they create the pizza in real time as part of that. I thought that was a brilliant, brilliant analogy. As we start to think through it and a lot of what we're thinking about is like, how do we provide the infrastructure for builders to build on top of, you know, on top of us, Whether that is, you know, the communications channels to drive conversations, whether that is the data to be able to understand the memory and create that great experience. But I do think there's a world where you will create more real time applications based on what you as a marketing leader need. And a lot of where we've pivoted as a company is this notion of builders. Right. And I think for a long time Twilio specifically thought about builders as developers. But you're sort of democratizing this over time. And you even described it like, I'm not a technical developer, but I can go do and use these tools myself. I think everyone's going to be a builder. And I think that's the part that's really interesting where you can say, hey, this is what I'm thinking about. Help me build this out. Here are the systems I want to hook it into and you could do that through natural language. And you're going to get these real time applications being built. I think the security network, the security pieces of it will get hardened down and others. But that's probably where the future is going. And that's both exciting, but also from an industry perspective it's a little bit like, wow, where is this going?
- [13:45]
A
Yeah, maybe this was our future of personalization, like building software that is personalized for anything you need within the space.
- [13:56]
B
Yeah, I mean, and I think that the notion of why has it been so hard? And one of the things I've been talking to my team, we're talking a lot about where imagine today as a marketer, what's often the scarcity of why personalization is hard. It's the data which is sort of ubiquitous now. And you know, we've got systems that can help around that, but it's often the content. And I think one of the things that always makes it difficult as a marketer is how much content can I create to create those micro messages for the personalization of that one to one, we've tried it for a long time. I've been talking about this for 15 plus years. But it's really hard to scale the content because you've got localization and you have the taste and the brand and all of those things. But what happens in a world where content is sort of no longer scarcity? You actually have more content than you know what to do with it because it's so easy to create. We're seeing this now and now with digital marketing and others where you have a lot of this notion of AI slop that's out there, then the differentiation isn't the content, it's actually how you apply the content to that specific individual consumer, whatever it is. And that's again a very different paradigm where you have an abundance of content versus a scarcity. And what do we do with that?
- [15:17]
A
Do you see consumers mistrusting content eventually? Because I'm just thinking about if a company is surfacing content to me where I know it's hyper personalized, it's a little too personalized, it's been learning too many things about me and I'm like, okay, I don't know. I think I'd rather read a more generic one that's truthful than catering content around me. Because you've seen everything I put online since I was five.
- [15:41]
B
There is a balance of invasion of it feels privacy versus feeling like it's relevant. And I think that's something we're going to be challenged with. One of the things I've been thinking a lot about is this notion of how do consumers take back their identity and data? And we've been talking about this for a very long time and obviously Google with the cookies, that was one where brands had to do a much better job of getting zero party data and first party data around that. But I can't imagine a world where, and I think this is where agents potentially play is what if this world where instead of me going and trying to find a product or information about something on a website or multiple websites or in a search engine or through the LLM, what if I just have my agent do it on my behalf and that changes the dynamic as a marketer where now I've got to go engage with someone's agent and then it could get back to that world of here's, here's where I want to share. This is the information I want to share with brands around that so they can personalize it based on the information I share, then it doesn't become creepy, it becomes relevant. Because it's, it's what I, what I've decided to share versus what they found out about me by linking my, or stalking, you know, my social media, you
- [17:04]
A
know, like I did for you.
- [17:08]
B
Yeah, this is a new world of, of research. Yes, 100%.
- [17:12]
A
So I mean I'd love to dive right into this piece that I know it's new and I know you're, you said that you're still trying to figure out exactly what it looks like having agents come and you know, now you're all of a sudden selling to agents instead, especially with the space you're in, which I know it's not just developers anymore and maybe eventually we can talk about the rebrand that you did because I think it's really cool. But what ideas or experiments are you all thinking about right now when it comes to this agent to agent buying experience or just agents coming and looking at you, or even just LLMs looking at you and surfacing what they want?
- [17:44]
B
Yeah, there's a whole continuum there that we can spend some time and I'm actually bringing a global team together next week to continue to iterate on our plan for this. I think it started out with this notion of we went from search engine marketing or search engine optimization where we created lots of content for non humans so that we became relevant when everyone was searching for us that moved into the answer engines or geo or AO or however people want to talk through it, where the search criteria and the search behavior changes. Because in our example people used to search for, hey, I need an SMS API to embed into my product to communicate text messaging to my customers. Right. They would search for SMS API. Today that changes a lot. They're going to say, I'm building a new application, this is my customers. Here's what I'm doing. I need a messaging platform that will allow me to communicate with my customers. That's very, very different around how you optimize for that. And then the search, like where the LLMs and the models themselves, where they find that information has changed quite a bit too. So you've got, now you got to focus on documentation and Reddit and GitHub and like all of a sudden there's new repositories, new information, YouTube and videos. Like it's a whole new content strategy around how do you stay relevant when people are searching through the LLMs? Because the LLMs have become the new homepages around that. And you know whether, even if you go to Google, I don't know what the numbers are, but a Huge percentage of it is you're not actually clicking on the links anymore. You're just reading the AI summary because you're trying to find information around that. So that's the first step of, like, how do you change your content strategy to become relevant to all of these LLMs that are, are the new. The new way that people find information. Then it moves to a world where you've got people to agents or Gentiq, and you're seeing a big push around voice. We play a key role around that, both the infrastructure and some of the products that we survive. So humans are getting more and more comfortable engaging with agents directly. So human to agent and voice seems to be the channel right now that people are working through. And my sense is that there's still some hesitation around this because we're learning and the modeling and the tech is, is getting progressively better every day. But I think there'll be a world where that becomes normal, right, where, you know, the agents are so good, they have so much context around your history, all the conversations that you have that you'll just get comfortable. And in some cases, you may prefer to talk to an agent than to a human, because that agent probably knows more about you and your history than necessarily a human would be able to retain. Then I think you're going to get to a world where agents are starting to talk to agents. And I don't think. I think we're in the very early stages. And one of the things, being a tech company, being Silicon Valley based, I have to be careful that I don't take the early adopters of all the cool stuff that's happening and sort of extrapolate that around the world, everyone now is going to have their own personal agent. And this is the future in the next few weeks. But it is happening. And I think it'll happen with the smaller companies first out of necessity. And I think the larger enterprises will embrace it eventually, but it's going to take some time because of what we described. There are security concerns. They're larger companies, they don't adapt so quickly. So that was a lot.
- [21:23]
A
No, I mean, I think that's first of all, amazing overview of where things could go. Um, and I do think it's a good reminder that, yes, things are moving fast, but it is probably moving fast in a bubble, like, especially software companies, you know, people who are eager to try things out. But a lot of times when I'm talking to people in Austin and I'm like finding out that many of them haven't even used ChatGPT ever. And I'm like, okay, I'm in a bubble. No one else is doing some of the things that I'm doing. Definitely not the things that you're doing. So I think it is a good reminder that we have time and no one's behind. Some people might be, but most people aren't behind. They have time to experiment with these things and a lot of industries are going to take a much longer time. I mean banking, health care, there's a lot of industries that'll take a while to I think, start using these things.
- [22:11]
B
It's interesting. I totally agree with you because there are a lot of people that you, you speak to because we are in a bubble, right? Anyone that's, that's sort of living and breathing in this world. But I saw, I saw a post, I can't remember who it was that talked about, hey, there's this tsunami coming and most of the people don't even know it's coming. And then there's a lot of people that are like, ah, that's not really snob, that's not a big deal, like we don't have to worry about that. And I think it will have a bigger impact faster than we think. And what's happening right now is you have a group of individuals and I'd say the developers are probably the ones that are taking the most advantage of this because there is still a technical component around it and they're getting ahead because they're creating, you know, they're creating new products, new processes and they're, they're becoming so valuable because of what they can create. It's, it's a bit mind boggling. Right. And so, you know, my worry is that you create this class of AI fluent, you know, people that are so much more productive, valuable, like they can create their own companies in 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 you know, 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, that's going to be a tricky societal problem.
- [23:37]
A
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 like no one actually needed to know about those things. And the good technology went behind the scenes.
- [23:51]
B
So yeah, I mean it could be like, it could be a world where they don't know, they just 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 like Openclaw and some of these others where you're going to create very small companies that are going to be tremendously valuable and the world of these massive, massive companies with hundreds of thousands of employees, 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 going to figure out.
- [24:39]
A
Yeah, I agree. 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 clerk and Vercel and this and that. And I'm just like, okay, sure, send it.
- [25:03]
B
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 dividend. And 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 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 could 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. And 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, 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? That'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.
- [26:33]
A
So let's dive into brand. It's like you're reading my mind. That was my next question. So I was just gonna 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 in, looking and finding the information it needs for its user. Does brand matter?
- [26:53]
B
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, my short answer is yes. And it. 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. So I think the notion of a how, how companies do product discovery, again, that can be a consumer how they do product discovery. How, you know, 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. Right. 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. You 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, were 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 is this, am I going to stake what I'm building on top of that? So I think brand then rises like the awareness and you know, you're like, for us. Okay, if I need sms, like yeah, Twilio, of course. If it's some company I've never heard of, do they have the reliability? Do they have the availability? Like maybe, maybe I should figure that out or I'm going to go back and ask the agent, why did you recommend this vs someone else I might know. So I do think there's a world where brand 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.
- [29:09]
A
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.
- [29:29]
B
Yeah, it's, 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 we, when you describe something who comes to mind and those are really hard and they're really expensive. Right. Especially 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 important you stand for in your voice and your tone and like 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 or I need components of a new marketing automation tool. Go figure out what components I should go leverage as part of that. I'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'll completely trust the agents to do that on your behalf. But I still think we're pretty far away from that.
- [30:36]
A
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.
- [30:43]
B
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, ah, 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.
- [31:01]
A
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? Like what does that look like?
- [31:16]
B
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, 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 could measure everything. You feel really, really good about being very data driven, very analytical around that. So you almost had like two parts of it, 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 the measurement frameworks potentially are going to change overnight because our media strategy may be very different. There's a world where I have to go build way more content for the agents and the models than maybe for humans. And 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. Like there's no visibility around that. So 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. That's, you know, the work that you're doing is attributing to it.
- [32:56]
A
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.
- [33:12]
B
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 gonna do. We're gonna do a pod. We're basically a video podcast or webinar around this, and we're gonna have a guest who's a human, and 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. 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 Europe, of all places?
- [33:59]
A
You're gonna get in trouble.
- [34:01]
B
It 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 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. If 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. I think too often in marketers as a whole, we've been very focused on let's. 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 gotta take bets and try stuff, and if it works, great. If it doesn't, move on and try something else.
- [35:06]
A
So did it work? What happened?
- [35:10]
B
It's in process. So we definitely didn't do it just for, you know, for Europe. And I gotta get a readout from the 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 go experiment.
- [35:28]
A
Yeah, I mean, I told my team the other day, I'm like, hey, hook up Heygen and 11 Labs and do what you gotta do and just let a fake me interview Chris and see how it goes.
- [35:38]
B
I know we were chatting about this before, but you know the same thing. Like there's these new tools. It's like, I think eventually we're all gonna have these digital twins. And I was playing around with something where I didn't do it. I didn't have the time to fully build it out, but I did build a digital twin and hey, Jen. And I was playing and it's pretty good with not a lot of effort. And I can imagine a world where it gets back into the authenticity. I think that's the thing we're going to go solve is 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 and 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.
- [36:33]
A
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.
- [36:43]
B
That's a whole new world. I'll tell you something I was thinking about playing around with today. So we do major events and my team was saying, hey, listen, I was meeting with them last night, they said, hey, we need to start thinking about locking down venues for 2029. I was like, wow, okay, 2029, 2029,
- [37:07]
A
what's even happening then? Wow.
- [37:09]
B
That was when I was like, are these going to be a thing? And so I was asking my handy AI tools and 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 they'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, they just want to build the interconnections and meet with their peers. And it's all about relationship building, 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, 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.
- [38:38]
A
Yep. 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. 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 and know it's a great place that's curated to find your people.
- [39:22]
B
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 change that's happening in the world? You 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.
- [40:09]
A
Yeah. 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.
- [40:33]
B
Yeah, I mean, I think, I think there was a world where, you know, there was always a worry like, oh, we can't get people in the same industry together at a dinner or an event. And the reality is that's not true anymore. You know, 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 think that's the world. Because there is so much change and so much uncertainty and 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. There's a lot of opportunity for everyone.
- [41:23]
A
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.
- [41:33]
B
There's a lot, right. And I told my team it's overwhelming to keep up with, quite frankly. Of all the tech innovation that's happening, I think there are 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. And 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 15 minute video around that. Because I'm like I said, a sponge, learning, learning, trying to keep up. And it's exhausting. But it's also pretty exciting to think about where we're headed.
- [42:33]
A
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 does 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.
- [42:49]
B
I do, I do have, I do have a handful of. Of I. 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.
- [43:03]
A
Who's this for? Why haven't you said it yet?
- [43:05]
B
I want this, this is for like, 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. But 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 the 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 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. I'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, 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.
- [44:34]
A
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?
- [44:42]
B
There was one. I'm trying to remember which one it was now. It goes back to our conversation around AI agents and is there a world where agents are going to do the majority of buying versus humans? And there was a whole synopsis, 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. And one was a full article of 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 really hard. Like, I was just this morning waking up doing a summary of what Apple announced yesterday, where they're like, they've got a new laptop that you don't have to go buy a Mac Mini anymore and you can run it on your laptop. Right.
- [45:36]
A
Wow, that was quick.
- [45:38]
B
Yeah, I mean, they've just announced that, and they announced one that was 500 bucks. Right. So that it was more accessible for people. You try to keep up with all the chip stuff that's happening. The foundational companies continue to release new capabilities. It seems like every week there's something new that comes out. So it's a lot of work just to try to stay current, but it's pretty exciting if you can keep up with it.
- [46:06]
A
Yeah, man, I just bought a Mac Mini. Didn't even know that Apple was releasing a new computer.
- [46:12]
B
They did it yesterday, like, you know, in front of it. So, yeah.
- [46:15]
A
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?
- [46:35]
B
Yeah, I get the angst that I think we're all feeling. I 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 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? And 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 off site 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. A 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. So I think if you focus there and the tools enable that, that helps a lot as well.
- [48:59]
A
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?
- [49:10]
B
I am ready.
- [49:11]
A
Okay. What is a trend that you're genuinely betting on that has nothing to do with AI?
- [49:17]
B
A trend that has nothing to do with AI. My gosh, I don't know any trends outside of AI.
- [49:22]
A
I'm stumping all my guests with this one.
- [49:25]
B
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.
- [49:49]
A
Yes, I 1000% agree with you there. What is either a book book or a podcast that everyone should be reading or listening into.
- [49:58]
B
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 in 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, 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.
- [50:31]
A
Yep, I do. I love that one. What is something outside of work that's made you better at your job?
- [50:37]
B
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 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.
- [51:12]
A
I love it. And do you have kids?
- [51:14]
B
Yes, two kids, 19 and 15. So I'm in the fun teenage years.
- [51:20]
A
Yes. Okay. I'm so far from that. My kids are 6, 6, 8, 8. So you'll have to give me your playbook when I get there.
- [51:28]
B
I don't think there is a playbook, especially now. Just as you go.
- [51:31]
A
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 the this entire list. So you made a bet of things that were in and out in 2026. Do you still believe that? Buckets, Hats. Bucket hats are in?
- [51:48]
B
I don't think they were ever in. They were. They will still be out 100%.
- [51:53]
A
Okay. Well, thank you, Chris, for coming on Marketing Trends. I really loved having you. Where can people find out more about you and what you're up to?
- [52:01]
B
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 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.
- [52:18]
A
I agree.