E48: Work Sprawl and the Future of Marketing with Global VP Marketing @ ClickUp, Kyle Coleman

As global VP of marketing at ClickUp, Kyle Coleman has some bold takes on use of AI in GTM.

We know that many buyers want their buying process to be completely humanless, and we need to allow for that to happen. In this episode, he shares his views on leadership and performance. My expectation is that myself and everybody on the team runs toward the fires, not away from them.

And he uncovers what plays he's running for efficiency while maintaining a high bar for quality.

Go look at the contractors that you have on staff, the agencies you have on staff, the tooling that you use. Go through the line and I can basically guarantee you're going to see some inefficiency, overlap, or bloat.

Previously CMO at Clary and Copy.ai, Kyle Coleman speaks from hard-earned experience on making GTM for SaaS companies actually work. If you're a GTM leader, you're going to find a lot of interesting moments and value in this conversation. Welcome to the Revenue Leadership Podcast. Podcast.

Today's guest is Kyle Coleman. Most of you have probably seen Kyle on LinkedIn somewhere or in other venues. He's had a really interesting and eclectic career all the way from SDR and AE to now senior level marketing leader with some awesome stops along the way. 6 years at Looker where he started in the sales dev org and then eventually came to run all of sales development and a bunch of other functions like optimization. Then Clary for almost 5 years where he ended up being the CMO in his time there. And now most recently a stint at CopyAI as CMO, and now he's at ClickUp as the global VP of marketing. And so lots of really interesting company journeys to unpack a bunch of lessons. And the topic for today is, you know, the changing requirements of marketing leaders and how The face of marketing is going to change and evolve and integrate in different ways with the rest of go-to-market. And I'm going to have a bunch of questions on how revenue leaders, sales leaders can best work with marketing and we'll meander through a bunch of semi-AI related topics. So Kyle, I'm excited. We can finally get this one done and appreciate you jumping on.

Of course, I'm looking forward to it. I thought we were going to spend an hour talking about just having the first name Kyle. Is that no longer the agenda?

We can carve out, you know, 20, 30 minutes for that. I mean, there's—

give the people the content they want, my friend.

There's an overrepresentation in Kyles who are current operators and also spend too much time writing stuff on LinkedIn between you, me, Kyle Lassay, and Kyle Lacey. Oh yeah, Poyer. I mean, he's a VC, so I'm sorry, but like there's an influencer community, then there's operators. And like most of the time operators don't do the, the like content game, but you know, Kyle's, Kyle's are representing. So here we are, here we are. We have to, we have to do our people proud. All right. So you started your career in sales dev and then started to increasingly take on a bunch of other stuff and then were in demand gen and then eventually executive marketing leadership. And this has been in through a really interesting time through the sales acceleration era, now in the AI era. And so I think there's a lot for us to learn from there, but I wanna start very broad and really hear your opinion on like, how much do you think the job of a marketing executive has actually changed through all of this stuff? Are the jobs to be done the same, but the tools are different, or has the job fundamentally changed in your mind, given the change in sort of paradigm and technology platform?

Yeah, it's a good question. You know, I've been in and around B2B circles now for a dozen years or so. So my, you know, I haven't been doing this for three decades. I can't tell you what things were like in the '90s necessarily, but through what I have seen and studied, it's honestly, it's more similar than it ever was different. I think the difference is not so much about what the mandate is, Kyle. The difference is the resources that you get to do it. And I have been amazed, call it in the last 3 years or so, what I can get done with a team of 4 people versus what used to take me a team of 40 people to get done. And that's the mandate that's changed. And that requires a depth of thinking. It requires a depth of understanding about real process that many CMOs, many marketing leaders have, I think, sort of lost sight of. And so I'm very grateful. To my SDR roots because you cannot be an effective SDR leader without really being strong at process management. And it really required me to codify and write down what are the standard operating procedures? How do we get from A to B to C to Z? How do we do all of those things? And then I've been able to take and apply that same sort of thing to the AI-ification, so to speak, of many things that we do in and across marketing organizations that used to take Fleets of people. Now we can do, with the right process managers and the right codification of those things, outsource AI.

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Okay, let's unpack this. We're, we're already gonna be off script, but so what do you mean it's about the process and this is, you're applying this to AI-ification? Like how is this different than how marketing teams use AI? Used to run?

I'm going to go back to the original prompt, which was, how's the mandate for CMOs changed? And I think if you spoke with many CMOs, especially at larger companies, they don't actually know how the work is getting done across their organization. And that's not excusable anymore because what that introduces often, and again, in my experience, is it introduces a lot of bloat. Not necessarily always with full-time employees, but I would recommend to CROs, CMOs listening to this, go look at the contractors that you have on staff, the agencies you have on staff, the tooling that you use. Go through the line and I can basically guarantee you're going to see some inefficiency, overlap, or bloat, outright bloat. And so what I have been really focused on is understanding how does work get done. How do we go from, in a, to use some marketing parlance here, how do we go from the campaign brief to all of the assets that we need to distributor to execute that campaign, the email promotion, the landing page copy, the social promotion, the executive posts on LinkedIn, yada, yada, yada. Like what does it take to actually bring a campaign to life? And in the past that took a campaign manager and a social media manager and a demand gen person and an executive ghostwriting agency and, and, and, and all these other things. And all of a sudden you're looking at a dozen people spending 40 hours a week for 3 weeks getting this thing across the line. Now you need 4 people, 3 people, 1 person who is really adept at codifying the best practice to take that campaign brief and create all of the assets that you need with the right AI workflows, agents, tooling, whatever. And that's a fundamental change in how your work is getting done. The CMO mandate is to make sure that the quality is still there. The positioning is right. There's value props genuinely are unique. You stand out in the market. You own different language. You evangelize the right problems, like that stuff is still the same, but how the work gets done is fundamentally different.

Hmm. And is it your belief that the CMO needs to be able to do that themselves as opposed to having, you know, like an operating person in their team that's doing it? How deep do marketing leaders need to go to actually like know how an AI workflow operates and what agents are doing what? What's your level of depth there?

I think it's a dereliction of duty to not understand how work is getting done across your department because you need to run efficiently. And I think that what I have seen, Kyle, especially in the go-go times of 2013 through '21, was we didn't care how much we were spending. And a lot of the reputation building was empire building. How many people do I have on my team? Remember, you used to hear people like brag about, oh, there are 90 people, 150, 300 people on my team. Like, that's not a brag anymore. It's almost the opposite. And so there's a responsibility to make sure that you are being a fiduciary inside and across the business and making sure that you do high quality work in a way that really is cost effective, that you're doing things that are actually going to yield the right kind of CAC, um, numbers that you need, the right kind of LTV you need, the right kind of metrics that are actually powering the business. So I'd say there's more of a responsibility for marketers now to be closer to the operating metrics of the company. And ensuring that the way that they're running their business, their department is in service of those metrics that the company needs to hit. So, by the way, I'm not advocating that you go and fire everybody, kind of maybe how it sounds. It's not what I mean. And a lot of the, when I have gone in and I, I have done this dozens of times now, I've gone and I've done this personally, but I've helped other VPs of marketing, CMOs, and even on the sales side go through and look at like, how does work get done? And oftentimes it's these things that have just crept in over time. Oh, well, we started with this content agency and then we layered in this one and then this, and now we have 4 different content agencies and we're spending $25K a month. I'm like, what? How did this happen? And like that, you'd be, you, you would be surprised how often that happens, especially as you accrue things over time. It's just like how you accrue SaaS tools over time and you're like, shoot, how did this happen? The same thing with contractors and with agencies. And a lot of times that marketing leadership is on the hook for that kind of thing.

Yeah. It's funny 'cause we're going through this exact thing right now as a part of our 2026 planning cycle is going through like line by line, vendor by vendor, agency by agency, asking ourselves like, is this absolutely necessary? Could we do with 50% less? Because there's lots of mechanisms to add things to companies that there's no, cadence or rhythm or ritual to remove things other than maybe annual planning if you have a CFO that has good stewardship. So very, very much agree with you there.

Well, and one thing I'll add to that, Kyle, just is on, on the mandate for the CMO. I think the mandate for the CMO now, now that you have streamlined the efficiency, you've eliminated the bloat, you feel good about the way that your, your company is running. The way that I view my mandate is I'm responsible for ensuring all of the people on my team are capable of the strategic thinking that's necessary to build a real marketing career now. So now that all of that run rate stuff, all of the, the, the menial repetitive tasks, now that all of that's outsourced to AI, that means we've created time for people to think and act more strategically. So what does that mean? For me, it means they need to really understand what is our company level narrative, what is our point of view, and they need to be able to extend the thinking of that point of view across their channels or with different audiences or in their events or in their content or whatever it is, they need to be true thought leaders. And if they're not subscribing to this new way of marketing, that's very much problem-oriented, that's very steep, super steeped in the problems that our customers are facing. It's not at all really ever feature-focused. Like if you're not subscribing to that, then I don't need you on the team. Like I need people that are willing and able to think at a higher level, at a higher altitude. And tell a different type of story. And that's what, that's the upshot of taking all the small stuff off their plates. It's not to get rid of them. It's to make sure that you have as many brains, human brains, not AI brains, human brains as possible doing the heavy lifting of real thinking. And that's really hard.

Yeah, that, that's the, I think the conversation that we're in, in so many different places right now with AI is like, well, is, is AI going to take all the jobs? Well, actually, if you, take a bunch of the stuff that's just grunt work and you outsource it to a model, then there's so much more room for interesting, thoughtful things. I think the nature of work is certainly going to change a lot. We're seeing this very much so in our business, but I'm not sold on all the jobs go away, but I am sold that you're going to need to be a much different operator in this world and be able to think strategically and in systems. Um, and so I want to go back to your sort of comment around managing the process and this new type of marketing leader. So bring that to life. Like what does it actually look like to dive in and see how the work works and what are you changing? And then what like process are you putting in place that wasn't there before?

Yeah. So I would say that from a marketing standpoint, from a marketing leadership standpoint, The way that a lot of our work is organized is around the concept of campaigns. We have a theme, we have an idea, we have a product, we have an event, we have something, and we're bringing it to market. And normally that's done through the wrapper of a campaign. And so what I try and understand is what is on the truck for the campaigns that we are architecting. And they come in different shapes and sizes. You know, a big product launch is a really heavy lift and you're gonna have to work across product. And enablement and sales and all the rest. And the set of deliverables you need for that is significantly different than a small campaign that, you know, you're doing a field marketing event in Toronto and you just need to get that off the ground. And there's flavors in between. So I want to understand what does our small, medium, large campaign mix look like? What do the deliverables look like and who's responsible for them? What does it take to actually get that event off the ground? What does it take to actually launch that product well? And who does what? And that's, you know, I just started this new job recently in the last 6 months or so, and that was one of the first things I did. Was just kind of sit back and listen to how things are getting done. And that with a fresh set of eyes, it's a little easier than if you've been there for a while and are precious about some things. But with a fresh set of eyes, I was able to see, okay, there's overlap here, there's redundancy here, there's inefficiency there. We could AI-ify that. Boom, boom, boom. Okay, great. And a lot of what my responsibility is, is talking to the people on the team. Ariana is one of our campaign managers. She's fantastic. She does so many different things, integrated marketing. She's amazing. Is like, Ariana, what is your process for going from this input to this output? What do you do? What are your steps? Okay, great. Here's the components of that that lend themselves to AI, and here's what doesn't. So now we need to create our AI workflow for this part, and then you still own this part. And we just line by line, you go through every single deliverable for all those different campaigns. You'll very quickly understand Where do you have overlap? And then what can you outsource AI?

Hmm.

But you have to know, you have to really know what does good look like and how do you architect the step-by-step process to get there. And I think the mistake that a lot of people make with AI is they go, write me a promotional email for this event. And it sucks because you haven't actually given it any instructions on what good looks like. You need to start the maze at the end and solve it that way. It's way easier to solve a maze by starting at the end than the other way around. And so like you have to have a perspective and opinion on what good looks like. And so do your, the people on your team. If Ariana didn't have a perspective on what a good landing page copy is and what's gonna convert well and what good promo emails look like and how to do audience segmentation, if she didn't have a good perspective on that stuff, she wouldn't be able to codify the process to outsource it to AI. Mm-hmm. So like that's the missing link that a lot of people aren't thinking enough about, and that's why they're inevitably disappointed with AI because their instructions are way too hand-wavy.

Yeah. And so that's really about the prompt engineering or the context engineering.

It's, that is the next layer down, Kyle. The first step is real expertise on how to do this well. So like domain expertise. So domain expertise comes first and then prompting expertise or AI-ification, whatever system you're using. And then you, with that, those powers combined, that's how you get a good output.

And are you requiring every marketer to develop the AI expertise or is that a central, is that a central applied AI team that people can tap into?

Yeah, it's a little bit of both, Kyle. So 2 years ago, I would have said yes, everybody needs to really understand prompting, go take a prompting intro course, et cetera, et cetera. At this point now, and I think this is going to continue to be the trend, you don't have to be a prompt engineer. You have to really know in, in natural language sort of ways, you have to be able to describe your process. And if you can describe your process in a natural language way, then there are other AI systems that can effectively do the prompting for you, or we're lucky enough to have internal resources that can build a lot of this using our own product. So we have a little bit of a, an advantage because we have a lot of the AI skills in-house. But again, this AI technology is pretty far along. If you can describe your process, like literally just in bullet points, what are the 10 bullet points that get me from A to Z and give that to any sort of AI workflow builder at this point, it'll do a pretty damn good job.

Hmm. And I would imagine all of the workflow management, the AI, that's all happening in ClickUp. Like that's your, your core operating system for basically everything. It is.

Yeah.

Cool.

Yeah. And the useful thing here is it has like, you have to have all the context. So especially for marketing deliverables, but the same is true with sales deliverables. Like I need to have my brand guidelines. I need to have the way that we talk about different features. We, we need to have all that stuff. To inform the AI workflows. Similarly with sales, like you need to have a perspective on what does a good cold email look like? What are the right things to sell to which personas? What are the right value props? Like you need to map that stuff out. So I'm like, I, I don't mean to skip over that. That's part of the domain expertise of what makes for a great cold email, what makes for a great promotional marketing email. Like you need to have that context informing your AI system and all these AI tools are making it easy to integrate that kind of stuff. The beauty of, of ClickUp is it's all just already in our platform natively.

Yeah. Yeah. I did a, I recorded something with Chris Cunningham like years ago and I hadn't really like checked out ClickUp in a while and I was like, man, this product has gotten really broad. And then before we, before we hopped on, I was like on the ClickUp site again this morning. I was like, this product is like massive now.

Yeah.

It seems like you guys just do everything for a company that wants to opt into the ecosystem. Is this, so you are a, like a traditional SaaS company now that is like, is becoming AI native or, you know, the positioning really feels AI native. If you, you didn't know how old ClickUp was, is that a challenge to convince people in the market that you guys are AI native? Like you are as much AI as like some YC startup. Coming out today?

Yeah, it's a really good question, Kyle. I'll kind of answer it a little bit differently, which is again, like, what is the evolving role of the CMO? And what do I think I focus on maybe more than others is I focus on evangelizing the problem. I think that there is a misconception and something that I've certainly have had to unlearn after my years of marketing training in school and then, um, bad leadership or bad advice is that I used to think, and I think many people still do, that the best product wins. And then I, then I use Salesforce. Like clearly the best product does not always win, but there's this, there's this, people want it to be true. You know, founders, especially technical founders are so proud of their product. They just assume it's going to be a field of dreams type thing. If I build it, they will come. The best product is going to win. And that's just not how it happens over and over and over again. You're like, man, I can't believe. That company didn't make it. They had a killer product. What happened? Yeah, yeah, yeah. And it just doesn't happen. And the reason it doesn't happen is because there's a very important narrative storytelling problem orientation that is critical to attracting an audience and maintaining an audience and architecting a different vision of the future that people need to subscribe to, to buy your product. And so what I focus a lot of my time and energy on is creating that problem creating language around this, that problem. This is something I learned from Christopher Lockhead in the Category Pirates. Evangelizing that problem with language that you own makes it easy to explain what you do. And the more you evangelize a problem, the more people assume you have that solution. And so as you think about, to finally get back to your, your question about like the AI positioning, the AI messaging, effective AI is all about context. If you don't have context, it's much harder to get effective AI outputs. And so we've thought a lot about what, what, how do we position that? Like, we're not gonna have to just, you know, change our name to ClickUp AI and just have a new logo. That's not, that's not gonna work in 2 years. In 1 year, that's like the appending AI to things is gonna, it actually probably already is a faux pas. We need a more nuanced way of thinking about what is different about ClickUp. And so we have this whole concept of convergence. Like software converging your docs, your chats, your projects, your whiteboards, your forms, all converging onto a single platform that's creating the context. So that's our solution. Prior to my joining ClickUp, they were really heavily marketing this solution and this positioning of convergence, and people were like, what, what exactly does that mean? It wasn't totally landing. And so I kind of inverted it and thought, it's not wrong. The solution is right. Convergence creates context. Context powers your AI transformation. Wonderful. That all makes perfect sense. But the problem wasn't very clear. And so we did a, I did this exercise. I asked the field, I talked to God knows how many customers. I talked to analysts. I was like, what problem does ClickUp solve? And I asked champions, I asked executives, I asked our seller, I asked everybody. I must have had 100+ conversations that was asking a very simple question. What does, what is the problem that we solve? And then I went, you know, into the lab and created you know, tried to create some, some new language around this. And the two-word phrase that we've come up with, and that's resonating really well, is the problem that ClickUp solves is work sprawl. Your apps, your people, your data, your knowledge, your context is sprawling all over the place. ClickUp solves that, creates 100% context, powers your AI transformation. And as people see that, and when we present this problem of work sprawl, you see the light bulb go off. They're like, yes. Finally, you get me. And then, then when we talk about convergence, they just see it as the antonym to work sprawl. And then when we talk about AI, it all flows and it all makes sense. So yes, we are repositioning as an AI company. Yes, there's a lot that we need to do to become known as an AI company, but it all starts with the high-level messaging, and it starts with a story that your sellers can actually tell. If your sellers can't tell that story, it is dead on arrival. Like, you could do the best marketing campaign in the world, you have the best website in the world, if you're still a sales-led company, And your salespeople don't tell that story because it's too complicated or it's fancy language or it's ivory tower type messaging, it's not gonna land. And so I, I've tried to be very intentional about that and tried to simplify the way that we tell this AI positioning and this AI readiness story. And, and that's the messaging hierarchy that we've come up with.

Yeah. The, the graphic that I liked on the site was like, it was like a little puzzle. Yeah. It was project management, like data. Data and not something else and then them coming together and then just like AI punched in, in the middle of it. And, and I think if you have spent any time trying to build AI solutions and, and making it work in your organization, you're, you're very familiar with the fact that it's, it's, you know, like, what do you, how do you jam all this context together? Because, you know, Claude MCPs into a bunch of stuff and you can use Claude code to get into these files, but then, you know, OpenAI has the, that can get you into these things, but not those. And you just end up in this wonky spot, which is not something that we have totally solved yet, but we hired a head of applied AI for, um, go-to-market to try to just like solve it in this part of the business.

There you go. Yeah, that's the right approach.

Yeah. I mean, it's, it's, I think going back to that question around You know, do you think that everybody needs to be AI native and know how to do the prompt engineering? I've actually gone, I think you need to know enough of it to understand the primitives and understand why AI does the things it does, or else you can't problem solve. But I also think companies need to have that expertise that people can tap into to go and like actually problem solve somebody, something and say. You know, actually it's not Zapier that should be in the middle of this. This should be with like an MCP or this should be something like natively that we're building in a custom tool. Um, so it's, it's, I think you have to learn the prompt engineering and figure out, you have to learn the first principles. Like I often ask people, I'm like, do you know the difference between pre-training and post-training? And most people are like, no, I mean, it's just like making the model. Right. And that would be an example. It's like, okay, well, you probably don't understand. Like the principles and fundamentals underlying this thing so that you understand what's happening above, you know, above the line, like when it hits a rep, like why are your emails like slop? Well, you've chained together multiple layers of generative outputs in a way where like, you know, you're stacking lossiness, you're stacking hallucination, which no Yeah, with no human in the loop, with no constraints or the right context engineering or like, but unless you understand how the prediction machine sort of works and understand the strengths and weaknesses of like the very fundamental tool, it's hard to make good decisions as a business process architect or like as a work architect. Yeah.

So I think that's pretty well said.

Yeah. I think both things need to be true. You do need to learn it. But the sophistication of what is possible now has me like pretty confident that we need real experts in-house to help take all of that to the next level. Even just like buff out the kinks, take something from like, you know, what I vibe code or like spin up in a custom GPT is going to be like fine, but somebody who lives in this all day long, every day, it's going to be way better.

Yeah, there's a difference between something being fine for one-off use and something being production ready for scale. It's a different beast.

You know, you're going to spend hundreds of thousands or millions of dollars against this output. You know, if it's campaign copy or cold email or whatever it might be, like you should be spending the cycles to really, really hone it in. Um, okay. So changing gears slightly, how has your leadership philosophy evolved? You know, in, in this, like specifically with AI, you as somebody who is shepherding the careers of a bunch of folks and thinking about how this whole thing stitches together, has, has that leadership philosophy changed very much?

I would say it depends on the team and the mandate of that team. So I have our XDR team here at, at ClickUp, and then I have our mar— our core marketing team, product marketing, field marketing. A content team that's based in India. I have a bunch of different teams and I think it, they require a different type of management and expectation setting and things like that. So is there a specific like role that you're curious about?

No, like as an executive, how are you, how are you managing your teams differently?

Like in a leadership sense, I would say the thing that's changed most for me is a comfortability, like this has really nothing to do with AI. So I'm going maybe a little bit Yeah, off of the topic, but the unlock for me is just being comfortable delegating and being comfortable pushing. And the, I think a lot of people are uncomfortable pushing because it is uncomfortable until you realize that if you think about the people in your career that you're most grateful, I'll speak for myself. The people in my career that I'm most grateful for are the people who push me. I don't remember the managers with whom it was an easy relationship where they just like, okay, check, check, check, have a good day. It was always the people that expected more, that gave me more, that allowed me to earn the right to take on more, that encouraged me to, to fail and explore those failures. And so I try, and it took me a while to like be comfortable doing this because I like being liked. It's nice, you know, I, it's, it can be uncomfortable to, to entertain that kind of, uh, conversation with a high performer because you don't want to demoralize them or you, you don't want to feel like, oh, if they get a negative feedback or something like, like you just have to put that outta your mind and understand that in order to scale yourself and in order to scale them, you have to raise the bar from a standards standpoint. And as soon as I really understood that, I started challenging my people in a very different way. And the mandate that I try and make very clear is my expectation is that myself and everybody on the team runs toward the fires, not away from them.

Mm-hmm.

You need to identify the problem areas and you need to go solve them. Even if you're not sure you can go solve that thing, if you go and you see that that's a problem and it's only tangentially related to your role, go solve it. Like go figure out how to put that fire out. And if we're doing that proactively, that is the type of career growth that people appreciate, especially high-performing people. And that's what makes for a really high-performing team as a whole. So that's my managerial philosophy in a nutshell. It's easier said than done, obviously, but it comes from a comfortability of like really challenging people and expecting them to do more like than they expect of themselves.

Yeah, we have a thing internally that we use a lot that we borrowed from 10A Tandon, which is like we want heat-seeking missiles for pain. Yeah, like we, we want people that just like have a nose for it and go flying at it and try to solve. If you can stack a bunch of those types of people in your organization, then special things can happen. I think the balance and where what we've, I think, done a good job at, owner, is having a bunch of these super intense people with very high expectations that want to solve problems, but still can treat each other really well. I think like you can pile a bunch of those people together and the organization can get a little wonky, but maintaining that semblance of like team orientation and camaraderie is underrated for sure.

It's funny you say that, Kyle, because I just recently had a conversation with somebody where I was like, look, people have to like working with you. If they don't like working with you, like you're, you have dependencies on, you're asking them for stuff. You're in their priority list. What do you think is going to happen if you treat them like shit? They're, you're going to slip off their priority list. You're not going to be effective. So like, I'm not saying put velvet gloves on and I'm not saying that you have to be like, you have to be, I don't know, you, you always need to have high standards, but be nice, be kind. It's not hard to extend the olive branch. Um, and so I, I totally, for certain people, but yeah, tough, tougher for certain people, but, and that's exacerbated by the remote environment as well. And so a lot of the advice that I give to my team is that you need to have real relationships with the cross-functional people that you work with. And you have to go out of your way to manufacture those things. I was talking to our head of demand gen and I was like, hey man, you need to have a real relationship with our second line sales leaders. Like, when was your last one-on-one with Lauren? Never? Like, you have to solve, go solve that. You should have a regular, and you need to own the agenda. You need to bring her something valuable. You need to add value to her day-to-day and have a real relationship with her so that you can be that heat-seeking missile, understand what the pain points are, get feedback on the campaigns, get close with our frontline managers. Like these are non-negotiable things. Your team is not just your team. It's like vertical. Your team is the horizontal ecosystem of people that you work with. And in a remote world, you have to go out of your way to create real relationships with those people. Otherwise you won't be nearly as effective.

So say more about why you think your first team is horizontal. And not vertical?

The reason is because especially at senior levels, it's a lot about dot connection and context that you have. And it's a lot about you being effective in shepherding longer-term cross-functional strategies. And that shepherding requires good relationships with people, but also a really deep understanding of what different teams and people's priorities are. And if you don't take the time to really deeply understand that and weave the connection, cross-functionally, you can't be effective vertically down across your team. I'll give you an example, Kyle. Like, I, um, ClickUp's been around 6 or 7 years. As you mentioned, this broad horizontal platform, we have all these capabilities and a very, very strong PLG, product-led DNA. And so we have this DNA that's very much feature selling and hey, what do you want to use ClickUp for? Use it whatever you want. Here are 10 licenses. Have a good day. And when I started, I was like, We have to productize this platform. We need to be much more, uh, opinionated about where to start and where to go using ClickUp. We need to scan across our most common use cases and we need to package those up, deck and demo and templates and AI agents and yada yada. And then we need to go create the right SKUs and we need to sell those things. If I tried to do that just up and down my chain of command, it's completely dead on arrival. Like I need solutions engineering, I need pricing and packaging. Obviously I need the sales team. Sales team, and all of those leaders have to be bought in. My service to my team, my marketing team, is to go and get the buy-in from all the senior-level stakeholders across all of those different departments so that we can have a real initiative that really gets across the line. And if I forego that hard work of getting the right people in line and on board and then just go do it anyway, it's going to be a failure. And so that, that's the way I think about things. Like, yes, your team is your vertical chain of command. but you have to focus first on your first team, which is your cross-functional peers.

Yeah. Do you find, I don't know if this is AI driven or if this is a natural evolution. Have you found the lines between marketing, sales, product, data, RevOps have blurred more in the last few years? I mean, you were an early person who's blurred those lines, but do you think it's a broader, a broader trend that these things have more overlap than ever?

Without question. Yeah, because executing has become more blurred than ever. It used to take humans monitoring product signals and executing those signals, and it made sense to have specialization in order to do that. Now we can monitor and action very complex signals much more easily in a more automated way. And so we don't need to have, as an example, somebody sitting on the website waiting for a website visitor to come and then have a live conversation with them. We can architect that playbook and then we can have the AI agent do that. So now I don't need a team of people that are specifically, uh, just sitting doing that one task, or I don't need, um, you know, let's use, I mentioned ClickUp has this PLG DNA. I don't need a team of people that are monitoring signals for product usage. Oh, they hit a paywall. I need to go send them an email. That is completely automatable. And so for that reason, like what used to be a sales action and a sales process to create a meeting or create an opportunity or create an expansion or whatever. Is now very much a demand generation one, like fully automated. The mandate that we have internally is to automate whatever is automatable. And that's for two reasons. One is to make sure that nothing slips through the cracks because human processes are broken because they are beholden or humans are beholden. Um, and they're going to be imperfect for that reason. So automate what's automatable so that we make sure that every time that paywall is hit, the right thing is sent at the right time to that person. But the other reason is because we don't want humans with brains wasting their time staring at an inbox and pressing send on an email. It doesn't make sense. We want them doing the more strategic work. So that's the mandate that we have. And the lines are very, very blurred for that reason. And traditional quote unquote demand gen is creeping further and further across that line, taking more and more and more off of sellers' plates in a very useful way.

Yeah. Yeah. And how these teams get architected, I think is going to be really interesting because there's, you know, these layering of skill sets, like the persuasion skill set is so valuable to bring into demand gen. I think that's sometimes what is missing in many demand gen environments. It's like people don't learn the old school copywriting stuff. Like maybe they, maybe they used to where you really got into the minds of a buyer. And because it's, it's so much more about optimizations and A/B testing and, but the, the hierarchy is going to be interesting to understand because, you know, for owner, for example, so we want to be able to, to serve the bottom of our market in like a much less hands-on way, have the product do more and more of the work and give the customer the opportunity to opt into, hey, like I need help. Can you get on a call? or the same way, like when there's a trigger, send somebody in, oh, you got stuck at this stage. We know that's where people struggle to get back on track. Okay. Put a, put a sales rep against that account. And so now you have product demand gen and sales all like doing something similar. Do you have an opinion of how that architecture will look? Like who owns what of the customer journey? Is it going to be different for every company? Like, how would you think about solving It depends on the company.

It depends on the complexity of the product. It depends on how self-serve it truly is. I mean, the answer, like any good question, is that it depends.

It depends.

Yeah. I would say, uh, the way that we're trying to do it at ClickUp is we're trying to outsource to AI or to automation anything that really is transactional. So anything like we want our sales process to be as frictionless as possible. We know that many buyers want their buying process to be completely humanless. Like we, and we need to allow for that to happen. That requires the product onboarding and enablement and learning experience to be world-class, especially with a product that has so much horizontal breadth as we have. Like it, you need instructions to know how to get started and where to go. So we're trying to create the right, um, sales systems to, uh, really sales processes, marketing processes to make that happen. but also the right off-ramps for sales reps. If you have a conversation with somebody and they're like, hey, I just want 5 licenses, just go give me 5 licenses.

Mm-hmm.

We also don't want a sales rep transacting that deal. We want an off-ramp to automate that. And so we're trying to find the right ways to make sure that everything that's transactional can get off-ramped so that our team can focus on real value selling, so that they can focus on real relationship building, so that they can do the things that are uniquely human. Kyle, that's the main, main thing is like, and I know it sounds like an oversimplification, But that's ultimately what it comes down to is what are the things that only a human can do? And if we get really good at those things, we're gonna have a distinct competitive advantage because most people are not very good at those things. And the irony is it's all the fundamental stuff that's been, you know, great sales for the last 50 years. And that stuff hasn't changed that much. So how do you build great relationships? How do you really go wall to wall? How do you have a real point of view about the account that you're selling into? Like, This stuff is traditional sales skills, Sandler, force management, whatever, like battle-tested. And we, I think I've lost sight of that because so much of sales became the science of scale and it's never really what great sales was. So I, I maybe I'm too much of an optimist on this, but I really think that we are gonna have a return to a lot of the relationship building and a lot of the things that made great sales great and great marketing great for that matter. By just focusing on the right stuff.

This is also my running hypothesis is that AI will allow sellers to do more selling because what, what has been one of the downsides of the CRM and sales acceleration era is reps spend so much time just pushing data around and filling out, filling out fields and updating records and it's not selling and the sellers don't want to do it. I don't want my sellers spending time on it. How do I get them doing as much face time with a customer as possible? We always say revenue generating activities over everything. That's like our mandate. How do we get people doing more RGAs? You can say the same thing for marketing. So in this world of like more blurred lines, who owns what metric? Because now I think in my world, it's sort of simple because like my target is actually a company growth target. I'm not accountable. I am accountable to the close one number, obviously that's, that's an input, but really the metric I am optimizing for is like, how fast is this company growing and how much enterprise value are we creating? Which means it's got to be efficient and low churn, high retention. But who owns the metric then? Like who owns the growth metric? If, you know, somebody, a customer can start in sales and then go to PLG or vice versa. How have you guys thought about that?

Yeah, it's a great question. Um, we have a, well, I own pipeline, so pipeline is squarely on me and this is even the sales source pipeline. I still feel accountability to make sure that the sales team A, has enough time to do what they need to do to self-source and B, has all the armament that they need from a messaging, positioning, sales collateral, et cetera standpoint. So pipeline, especially sales, what we call our, our, in our sales-led motion. That's, that metric is owned by me. We have on the self-serve side of the house, the product-led side of the house, we have a head of growth who owns the whole end-to-end lifecycle revenue for the self-service motion. And then my counterpart on the sales side are our heads of sales for commercial sales and for enterprise sales. So they own revenue and we try and keep it pretty simple like that. I own pipeline, they own revenue. Um, and then there's a bunch of efficiency, efficiency metrics that we're all accountable for and we kind of stack hands on, but those are the high-level delineations.

And how do you prevent squabbling or if a metric has two owners, then it has no owners on the growth and revenue number and because you're sourcing pipeline for both. And so how do you think about alignment so that people aren't trying to optimize for their own silo?

Yeah, well, we understand and I think this is where kind of our, we have a single owner. He's our COO. His name is Garav. He's like actually, I think literally a genius. He's extremely sharp. And he's across—

I bumped into him at GTM last week.

Oh yeah, I'm sure. I'm sure you did. Yeah, he had a great time. He's across all of these different businesses and ultimately he's responsible for the entire revenue number of the whole business. And so he helps us see across the aisle, so to speak, to make sure that we on the sales-led side understand how the self-serve side is feeding us and how the systems may and how what the investments that they make there have the impact here. So he helps us all connect the dots and stay aligned. There's friction though. Friction is healthy as long as you have the right conversations. You know, we, we have the classic friction between myself and the sales leaders. Like, are we creating enough pipeline? Are we converting enough pipeline? You know, and then we go back and forth on what coverage rates need to be and we hold each other accountable to improving our programs here and there. And so friction is healthy as long as you are open about it and there's a dialogue. And then we have the, the, the other of keeping us all on the same page.

Okay. That makes sense. Um, and so your AI, do you have like an applied AI team? You, you mentioned that there's like central folks. What, what is that today?

We have, uh, what we call our center of excellence team. This is a team that rolls up to me. They are, um, kind of quasi solutions builders, quasi product marketers. They're experts in ClickUp and they are doing things. They're building everything internally to power our processes and, and AI-ify our company. And they're building all the templates and agents that we use or that we sell into many of the ones that we package up and sell into our customer accounts. So we, we have that team of people. It's not a huge team that are doing the solution building. They also own like ClickUp University and a lot of that knowledge and training systems and things like that. So it's, it's a very useful resource that we are lucky to have. And a lot of it comes from our PLG DNA. Like we have to have this team to build up the university. So our self-serve users know the product. And then we can extend their usefulness to our sales-led business as well.

Very cool. I want to change gears a little bit. So do you operate that differently? So you came from CopyAI, like an AI native, like built in and scaled in this sort of on the back of the AI boom and ClickUp is now transitioning what seems like very effectively into this. Are there, are you operating the teams any differently in those types of environments or is it mostly the same?

It's mostly the same. I mean, the, the virtue of ClickUp is we have far more resources and so it's funny because we're, we're doing a similar at, at CopyAI, we had the concept of a maturity model and a self-assessment type thing and it was a lead gen capture tool and all the rest. And the way that we did it, myself and this one other guy, Nathan Thompson, we did this at Copy AI was like duct tape and super glue, just like super janky experience. And like, it was good enough for a Series A company. We're doing something very similar at ClickUp and now we have a real web engineering team and we have a real design team, like, and we have all these resources. And so we can do it in a way that from a brand standpoint is just next level. Like it's the same. Thought process, but the level of execution, the, I guess the polish and the precision of the execution, that's, that's the difference. So similar sort of strategies executed with different levels of expectation based on the different resourcing that we have. Okay.

That makes sense. And, and so is there advice that you would give to a more traditional SaaS incumbent trying to make this transition? So, you guys have an advantage because it is AI-centric. You could just call it AI-native. You were early and it seems like very far along this maturity curve, but a lot of companies are not there and they don't have AI built into their product in a way. ClickUp's interesting because doing cool, super advanced stuff internally is like you're dogfooding your own product. So I'm sure there's tons of resources to do do it. Yeah, that's not the case for most companies, you know, they're selling into like a traditional, more traditional B2B product, it's workflow management, but then everybody's trying to evolve themselves internally to be AI native. What, what advice do you give those companies? Like where, where should they start to, for, for marketing leaders, where should a marketing leader start to when they're thinking about, all right, how do I get an order of magnitude more efficient with these tools? Is there an assessment model? Are there like places that you think that, that, um, people should start in their org? Like, what advice do you give?

Yeah, well, obviously they should use ClickUp. Um, in a— that the right, the right answer is you as from a leader. And what I view my role as a leader is, and, and I learned this early at CopyAI, that when I was selling Click— when I was selling CopyAI, most people that I was selling to, they had no idea what was possible. Like, not everybody is living on Twitter and following the latest and greatest. Like, you and I know the difference between ChatGPT-4 and 4.0, but most people do not. Let's leave 5 alone for the time being. 5's gotten beat up enough. Like, most people don't know this.

I'll say. Yeah.

Yeah. Um, so what was kind of a revelation to me was the first thing that you need to do as a leader is you need to expose people to what is possible in vocationally, in their domain. What are things that you can do? Like I, I actually recently at ClickUp, I sent a note to our team channel. It's like, did you know you can screenshot a dashboard? You can upload that screenshot into what we call ClickUp Brain and you can ask it like, tell me the trends and it'll do it. Like, did you know that that's possible? And half the people did and half the people were like, oh my gosh, that's amazing. And so like exposing people to that kind of use case, exposing them to how to think about what's possible is the right kind of light bulb moment. And from there, the next thing that I did is every week, every single person on my team is responsible for submitting one AI use case. Doesn't have to be new. Doesn't have to be revelatory. It doesn't need to be something that's productizable and going to make millions of dollars. Did you use AI SDR to research that person ahead of a call? Great. Like submit one AI use case per week and that compounds and you start to see people learning and you start to see people commenting on other people's submissions and like, oh wow, share your prompt. How did you do that? You have that agent, you have that automation there in ClickUp. How'd you do it? And you just start to, you manufacture the conversation. And I would say like, this is kind of quintessential leadership tale as old as time. Change management is hard and it has to be tops down. And if you're expecting your quote unquote AI mandate to be, use AI, see you in 3 months at our next all hands, it's not going to work. Like you have to live it yourself. You have to understand it yourself, share examples, and then create some mechanism to get your people excited and engaged about what's possible and then hold their feet to the fire from an accountability standpoint to make sure they're doing it. Yeah.

Yeah, that makes sense. There's a book by the Heath brothers that I like called Switch and, and, uh, Dan Heath just wrote a book called Reset, which I only started listening to last night after it was recommended in, in the, because the subtitle is how to change what's not working. And so I'm sure there'll be a lot of lessons from Switch that, that carry over, but the, the change management piece is so underrated at the talk I gave it at GTM. This was like a footnote that I sort of expanded on and I'm, and I'm I kicked myself that I didn't have more slides on it because I really believe that the companies that will, companies that will take the most advantage of this new platform are the companies that can digest the most change, both at a leadership level that we're talking about, but at a rep level, think about how much we're changing their, like people's day to day. And it's easier when you're a participant in the change, like when I change a thing of how we work, I'm excited about it. But if the change is happening to you, it's much more difficult to internalize oftentimes. And so the rigor around how you execute change management, I think is so underrated. And we, for the last, I don't know, 18, 24 months, I've had this traffic light model. You could have a green, yellow, or a red light change. And that has a bunch of different expectations of the communication that needs to get done around it. How does it cascade? And we're still like, cause we were, we just like kept launching things and people were, our reps were basically like, you got to slow down this. Everything is chaos. Like it's too much. And, and, uh, it was like the number one thing that came out in this engagement survey. And it was really good feedback because it made us, it made us get serious about it. And now we feel like we have a good muscle. We don't, we try not to do too many big things at one time. But in retrospect, like it was reactive to the feedback from our team, but in retrospect, it is actually like now given us this platform to, to advance the business in a way that like is not otherwise possible because either it creates chaos or you launch a bunch of change, but nothing happens. The, the, the behavior of your team doesn't move. And then you've just sort of like spun, spun your tires that change. Management, like muscle, is, is one that I think doesn't get enough attention.

I totally agree. Yeah.

Um, okay. So we were talking about the transition, like how companies can think about the transition. So the art of the possible is certainly a big piece of it. Leading from the front and setting the expectation. Are there any particular parts of a marketing org where you'd say to folks, like, that's the first place to look in terms of accelerating with AI or automating? Like, how do you think strategically about use case priorities? Organization?

Yeah, the first place to start is, I think the place that makes the most sense to start is in a kind of quasi-content waterfall, which is most, most marketing teams are running virtual events. Most, maybe not all, but most. And if you are one of these companies and you have a virtual event cadence, you have transcripts. And those transcripts that you have from those events are theoretically at least your best presenters or your best thought leaders or your best customers or whomever. Telling a great story about how they use your product or what's new or what's wonderful or whatever. That transcript in a past life would take a lot of time and energy to turn into serviceable content. Mm-hmm. And now it doesn't. Now it takes great workflows to turn that raw transcript into great content. And that's a no-brainer place to start. And the reason, Kyle, is a lot of what we talked about before. The context is all in the transcript. You don't have to do anything super super fancy to incorporate any, uh, net new context into that. Brand guidelines and your structure for blog posts or whatever is, is, is easy enough. A lot of times in my past, especially if it was like a more technical webinar or something that was like more product-oriented, that knowledge is just trapped in a sales engineer's head. And asking the SE to write a blog post while they're spending 12 hours a day on sales calls, like, it's never gonna happen. But now it's like I have it. It's all great. And so like now that you, you have that, you've built that muscle and you're like, okay, great. Here's how we can take a transcript from a webinar. We can turn it into social promos and email promos and long-form blog content and thought leadership content. And okay, great. We have this cool waterfall. Now you have the muscle to say, hey, what if I just go ask this product manager to riff for 5 minutes on the roadmap? Just record a voice note and just tell me what's going on and I can turn that into a content waterfall and you can start thinking differently about what are the raw materials that you need to create great content and where is it trapped in the heads of the people that are live across the business. And I think that is a no-brainer place to start for marketing teams.

And it's so much easier to interview people than it is to ask them to write a thing like, hey, can I put 30 minutes on your calendar to just ask you a bunch of questions? Everybody says yes to that. There's no crap. It's not that hard. Writing does force you to think more carefully about something, which I go back and forth in how much I want to do blank page writing. I was on the plane home and it didn't have Wi-Fi and it's a weird place to dictate, but so much of my writing flow now is just like I hit the function key, which is my WhisperFlow hotkey, and I just yap and I'm like, hey, I want to write this. Post about lossiness and here's where I want it to be. Like, do some supplemental research, give me the fundamental book, blah, blah, blah. And I had to do it staring at the blank page. I'm like, oh, I'm just like so useless now without my little super, super intelligence friend beside me. But, but I think it's a, it's, it is such a good example of how you can make it easy to just manufacture content and get better. Like, this podcast, like the transcript goes into my Claude project, which has the prompt and all the context. And then, then I do like a 20-minute, I do like a, you know, a 10-minute Claude artifact edit where I'm like, like 0.3 replace with something else that I had in my notes. And like, this is too obvious. So like, make it more sophisticated. So I do like a 10-minute Claude edit, and then I'll do a 20-minute hand edit to make sure that it's like up to a standard. And then I publish.

There you go.

Those would take 3 hours, 4 hours before, because I did the first couple podcast newsletters by hand. It was like literally 3 hours doing it by hand.

But it's a good exercise because you get that structure for what it looks like done.

That's why I did it.

Now I have, now this isn't slop and I feel good about this. My only quibble is that you should be using ClickUp's talk to text and not Whisperflow, but we'll talk about that offline. But yeah, that's it.

I was on I was actually on ClickUp and I was like, I wonder, cause I'm looking for a personal CRM. I, so many people reach out, they're like, I'm looking for a sales leader. I'm, I'm looking for my next gig. I'm this and that. And I, I'm, I want a personal CRM that I can just like have the recorder in my call and then have it like update the record or I can just like quickly do a thing and log the LinkedIn message or the whatever. ClickUp looks like a big platform for my purposes, but if it works, we're not supposed to be pitching here, so I will refrain.

I've been, I've been a little tongue in cheek, but we'll, we'll talk.

Okay. Yeah, man, I'm open to it. It's funny because, you know, it's all outside of my day job, but, but I just end up making like intros for people or, you know, like a bunch of cool, we use a bunch of cool, um, technologies. And so they're like fundraising. I'm like, oh, you should talk to X, Y, and Z. But it's so manual right now. But, and I have these lists that I keep that are just like crap. So if ClickUp solves it all, let me know. You'll be in their song and it'll be perfect.

Yeah.

I'll do, I'll do the evangelist thing if somebody can help me set it up. So one, we may have answered this question, but I wanted to ask a slightly different version. So the rate of company creation has never been higher. Like the number of productivity tools that are spun up by AI. AI project management, AI this, Granola, Fireflies, all this stuff. So there's more proliferation of people that compete with some part of the ClickUp platform. How do you think about standing out in this market where there is, and the volume of noise, the volume of like email noise and fundraising noise, how do you think about standing out uniquely in this day and age?

It plays to our advantage, Kyle, because our value prop is the exact counter. To this noise that's created, we are combating the problem of work sprawl that everybody feels like they're a victim of. And whether that's because of the proliferation of apps that they've bought that they aren't using, or whether it's because their data is locked somewhere that they can't use it, or their team is all spread out and the context is trapped in team, like people understand that this is a problem and more apps is not going to solve the problem. Like we just went through this with SaaS sprawl. We were just there very recently. Yeah. People saw it and they got burned. And so people like, we have an advantage for that reason. And this is part of the reason why this positioning and the messaging, the thoughtfulness that went into defining crisply, defining our problem was so important was because people see this phrase and they're like, yes, help. And then we start conversations. So yeah, channels are busy and yes, email inboxes are full. Flooded. And yes, there are a million different AI apps for all these different things, but our value prop sticks out because it is different and it's using different language that is resonating really well.

So make— so take ClickUp out of it now and make— and more generically, just everybody's market's busier than ever. Yeah. How would you advise CMOs to try to, to stand out above all of it?

Yeah, I would say, and, and I, I subscribe, as I mentioned before, to the category pirates. Way of Thinking. This is Christopher Lockhead and team, a literal Substack you can go subscribe to. Or if you, you have time to read one book on the topic, read either a book called Play Bigger or a book called The— it's so good— or a book called The Existing Market Trap. You can read that.

I haven't heard that.

It's kind of like, it's funny because The Existing Market Trap came out later, like years and years later, but actually serves as kind of a prequel to Play Bigger that sets the stage for why category design is so important. And what you will learn, and the big takeaway, is you have to own the language. You have to name, frame, and claim the problem that you solve, and you have to do it in a way that is new and different language that gets people. The reaction that we're trying to get from people, Kyle, is when I say work sprawl to people, and I wonder if you have this reaction, the reaction is, huh? Ah, like that. Like, what is it? It's different, but it's familiar. It's already imbued with meaning. Like if I If I had to define it, I could, but tell me what you mean. Like, that's the language that you're trying to create because it just burrows into people's heads in a different way. And that's the responsibility of, of CMOs, of product marketing, of positioning, is to do that. If you do that well, you will break through the noise because you're thinking at a different altitude and you're solving a problem and you're not just going and selling a product, you're selling a problem. And that's the way the buyers buy. Buy. And this is consumer products and this is tech products and everything in between. People buy to solve problems. So evangelize that problem. And anyway, that's, I would highly recommend that's what you do because all the other stuff that we're talking about is just excuses for bad positioning. Yeah.

Yeah. The tricky thing is everybody tries to create their own category and then you have no idea, like I have no idea what you're talking about.

So notice like I'm not at all talking about the name of the category. I am talking only about the problem that we're solving. I think that the problem definition and identification is the critical part to the way that you're positioning your product. The name you give the category is— it's important. I don't mean to discount it, but it's somewhat ancillary. Like, if you can't describe your problem really well and evangelize the hell out of that problem, the category is meaningless. Like, you need to convince analysts that your category exists via the problem that you solve. Not based on the name of the category and the cute acronym you created. Like, who cares? So I like focus on the problem definition, identification, and the rest will fall into place.

Yeah. My, I'm curious on your feedback on this. So my biggest gripe with product marketing and positioning and all this stuff is that what you end up, what I hear as the buyer is like, we are an agentic platform to accelerate the transformation of value in your company. And blah, blah. It's like, dude, what, like, what are you talking about? Like what, like I have no idea what your product is. You're just like, it's a bunch of buzzwords. And, uh, I sort of glaze over as a buyer. And so actually part of how I teach my teams to position the product is like, hey, look, like before we're going to do it, let me just lay out like what Owner is and where we fit in. And so I actually tell them to feature dump right off the top. I'm like, So owner is like everything you need to, to like win online, but it is website, online ordering, email, text message marketing. I'm like, I tell them to list, like actually list what are the things like, what, what are we talking about? Because going back to another Heath Brothers book, Made to Stick, it's gotta be concrete. Like you, you have to make it clear and easy and simple. It's like, okay, so we're talking websites. I, I like now I understand where, and then we can get into and where owner is different. Is, you know, you lose flexibility and choice, but you opt into a proven operating system that will win. And it's like, okay, now I get, it's like proven operating system within the construct of websites and online ordering and all of this different stuff. It's just like the people get way too cute with this stuff. And then you just have no, like no idea. I can't, the number of cold emails I get where I'm like, I have no clue what you're trying to sell me. And I'm like, definitely not taking a demo. But if, if you emailed me and be like, hey, we have the, like Superhuman does a good job at this. I think I use their email product and I love it. It's just like email with like tons of shortcuts and automations. I get that. Okay. I'm, I like, I like hotkeys and all this stuff in, in other places. That's my style of operating. So it's like, Now talk to me.

Yeah.

Uh, what's your reaction to that? Am I a bad marketer? No, no, no, at all.

Get you like, get them if they're in the grocery store, tell them what aisle to go to, like, you know, and then you can be more specific. And the way that you're approaching this, I think makes perfect sense. I think the way that I'm approaching it is somewhat different, but it's the same philosophy, which is I want to make the problem concrete. And that's the aisle in the grocery store I want you in. And I'll tell you how and what bag of chips you need. Like that. That's the way I go about it. It's the same, it's the same concept though. It's like we need to make something concrete so that they can attach to something. And the way that I think about it, Kyle, and probably sounds like pretty similar to you, is I'm very mindful about what is the conversation that they're going to have internally after this call.

Yeah.

And what is the one line I want them giving about what we do? And I don't want them saying that we compete with X, Y, or Z competitor. That's not the takeaway that I want. I want them to, you know, we solve a fundamentally different problem in a unique way, and I want them to be able to explain that problem succinctly. And so that's the way that I approach it, but it's, we're, I think, coming at it, the same problem from slightly different angles.

I really liked the language you put around it. If you haven't read Pattern Breakers by Mike Maples yet, you're going to really like it.

Yes. It's the best.

His whole choice versus comparison thing is, so I've always taught, not always, but the last like 6 or 7 years I've taught what I call point of view positioning. So like, don't try to sell the product, sell this point of view. And if you believe this, then uniquely Owner or Shopify or League are the only companies who solve it in that way, if you believe this point of view. So Owner's point of view is restaurant owners don't want to be digital marketers. And so you should opt into a system that is opinionated, low choice, but therefore gives you the best, best results. Because we've got an army of experts doing all sorts of experiments and then upgrading your website every single week, which you can't do on other platforms. And so like, that's the point of view. And either you're like, no, no, no, like I actually went to design school and brand is everything. I have custom fonts and we can just say, hey, it's not the fit, you know, like you're not going to like Owner. And so we can all save ourselves some time. But that choice versus comparison or the quote I used to, that's in all my point of view positioning stuff is compete with no one and no one can compete with you. And so you're uniquely like, I like your work sprawl thing. If you own, it's like, we're the company that fights work sprawl, then you, then it's like, okay, like I get it. Yeah. That's, uh, that's cool. So we'll do a quick fire and we'll wrap.

Sweet.

What separates a good CMO from a great one?

Influence, internal influence. You've got to be able to sell your ideas internally. And most CMOs sleep on internal marketing. And if you're not leading your company internally, then you're a service organization. And that's fine, but it's not what great CMOs do.

What's the most common advice you give to your new leaders or like VP marketing mentees?

Yeah, we, we talked about this already. So forgive the, the broken record here, but run toward the fire. Go find, seek out the problems, put that fire out again, even if it's something you're not sure you can do. Go have the confidence to come up with a V1 solution and the confidence to pivot if your V1 solution doesn't work. Like we need, we need you to go do that. If all you come in here is maintain and optimize, it's not enough.

Yeah. Um, what's the hardest lesson you've had to learn?

Again, like I think we talked about this, but I would say again that the best product doesn't win. And like, I, for whatever reason, I don't know why, I, it was just kind of built. It was kind of the way I thought about things. Like, of course consumers are going to buy the best product. And then the more layers I peeled back about human psychology and decision-making and Silicon Valley and what sticks and what doesn't, the more I realize how much of a narrative brand storytelling wrapper there is around all these things and how much So many other factors play into things. So I think you, like, especially, I know, like, many tech founders will listen to this, like, you gotta lose a little bit of preciousness. Now, of course, believe your product is the best. I don't mean to say that, but product alone is not going to win. You have to think bigger than that.

Yeah. All right. Last question. Best thing you've read in the last 12 months?

Ooh. Um, I. Read, um, I, I read a lot of business biographies and a lot of other biographies. I find that to be a little bit more interesting and like mentally stimulating to understand how other top performers got to where they are in life and how top business leaders got to where they are in life. And then like, yeah, instead of reading a book about marketing and then translating marketing principles, I like to read about how did Sam Walton build Walmart and like what did he do and then see what translates it. I just find it to be be a more interesting neural connectivity exercise for me. Um, long way of saying I went on this tear of reading Tiger Woods, LeBron James, and Kobe biographies. Just like fascinate, like fascinating. One of, um, our COO, his name is Gaurav, I mentioned earlier. He, uh, one of his main principles is you have to be effective in your role, but you have to be obsessed. And he uses this word very intentionally, uses it very often, and that word is obsession. And Tiger, Kobe, LeBron, man, obsessed. And when you just learn about their craft, I just find the work ethic inspiring. So like, that's been the best thing that if I had to recommend a trio of biographies, like, and you're remotely interested in, even if you're not interested in basketball and golf, like the dudes are really impressive. So I just kind of like blew through all three of those biographies. I was just motivated. I'm getting chills. Oh, Michael Jordan was the other one. Oh yeah, yeah, yeah. Amazing people.

I have the guy coming on who created the Mamba, Mamba system with Kobe.

Yes. Awesome. That's very cool.

Yeah. All right. You got to go. Thank you for joining. This was awesome. Uh, you can find Kyle on LinkedIn, you know where to, you know where to get them and you can follow all things.

Say hello there. I'd love to hear from you.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link in the show notes and be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.