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Daniel Murray
You know what's not fun? Spending your days in workflows, writing content and dragging blocks around the screen. You know what is telling ActiveCampaign's AI? Your marketing goals and watching it build the campaign for you. Emails, landing pages, follow ups, done. It's the way marketing automation should be. Start your free 14 day trial right now@activecampaign.com that's active. Activecampaign.com welcome to the Marketing Millennials, the no BS marketing podcast. I'm Daniel Murray and join me for unfiltered conversations with the brains behind marketing's coolest companies. The one request I tell our guest stories or didn't happen. Get ready to turn the up. What is Kyle, welcome back to the podcast. Excited to chat with you. You've been in so many different roles, seen you grow from being in sales to now all the way, like in leading marketing teams, which is cool to see. Well, thank you for coming back.
Kyle
I appreciate that. Yeah, I'm looking forward to the conversation. Daniel, it's always fun chatting with you.
Daniel Murray
So you want to give just a little background where you're at right now and like how you got to where you're at and then we'll talk about what's going on at ClickUp and what problems you try to solve.
Kyle
Yeah, for sure. So I'm the Global VP of Marketing at ClickUp. At ClickUp we have two different revenue models. We have a product led growth revenue model and then we have a sales led revenue model. I'm responsible for creating all things demand pipeline, generation awareness for the sales led motion. So my team is sales PMMs. It's content and thought leadership. It's demand gen and marketing operations. And then of course, near and dear to my heart is the SDR organization that also rolls up to me. So that's kind of how I was raised. As you mentioned, Daniel, I was raised through sales. I started my tech career as an sdr. I ended up leading a rather large SDR team. I did the same thing at my next company and then I kind of stumbled my way into cmo, into, you know, I've been a CMO twice now because I care about broadcasting messages as broadly as possible and, and I know to what extent pipeline is the driver for a company's growth. And I just saw the impact that marketing teams can make in doing both of those things. And that's why I gravitated more toward marketing than staying into more traditional sales.
Daniel Murray
I want to go into the problem you're trying to solve right now. I know your Boss is very big on giving people big hairy goals for everybody in his team. And you have a big goal of solving like how to get to 1 billion ARR. Could you unpack that? Why is the goal of that and how are you working backwards to get to that goal?
Kyle
Yeah, it's a great question, Daniel. So the high level goal is to get to a billion dollars in ARR. And it's something of an arbitrary number. A billion is a nice round number and it's aspirational and it's cool. And very few software companies ever achieve that mark. So it's something of a rallying point. But what's underpinning that goal is to be an enduring, legendary company that is fit for public markets, that's profitable, that's attractive, that's known for the sales organization we have, that's known for the product and for the customer experience that we deliver. And all those things combined means we're a billion dollar company. And so that, you know, it's billion dollar ARR is sort of shorthand for all the other supporting goals that we have. It's also a rally cry for the company to say we. What got us here is not going to get us to this next level. We need to reinvent ourselves. We need to hold ourselves to different standards. We need to find new and different ways to generate pipeline, to generate revenue, to do these things that we've never done before. And if we just try and continue to run the old playbooks, it's not going to work. So that's why having bigger, meatier, hairier goals is important, is because it requires people to think and act differently. And I'm happy to dive into some of those different ways that we're thinking and acting, but that's kind of what's underpinning that $1 billion number.
Daniel Murray
I really like those big hairy goals because I think one, it gets leaders and then people under leaders to think creatively of how to achieve that goal. If you have like an easier or like a semi good goal, big goal, you might just do the basic actions to get you to X goal. But yeah, I want you to unpack like how you are thinking of breaking this down. I know you come from the mindset of marketing and sales working well together, having a good system. So how do you, how do you unpack this for us?
Kyle
Yeah, yeah. So. So with respect to the company level goal and what Gaurav, our COO talks about is this billion dollar number. As we just said, my goal that he gave to me, the, the number that's on my back. Daniel is. And he's very clear about this. And I think he's right to be clear about it. He's like, I don't want you to just come in. And the same thing that was already. Is going. Was going to happen at the company is what happens. Like, you need to provide incremental value, which is to say value on top of what would have happened without you. And the number is $100 million. I need to create $100 million of incremental pipeline this year. So what am I doing? Like, there's a million things that I could do to try and get to that $100 million number, and I'm happy to talk through a handful of them, but I'll pause there. Any questions or comments about that?
Daniel Murray
No, no, no. I love the thought process. I mean, I think a lot of market. I like that how he thinks like that. Because a lot of marketing departments, you just. If you add someone, you might just be like, in a year, we went to X amount. But, like, you don't really know, like, the impact of that person to your team, especially a leader to your team trying to create an X goal. So I like that I need to create an incremental amount. That ClickUp probably is going to grow X amount this year without you. So what are you doing to unpack that? So we should talk about, like, let's. Let's get into, like, how you think about creating that $100 million.
Kyle
Yeah, yeah. So there's not. I don't have it line itemed out yet where I could put like, this. This line item is going to be worth 15 million, and this one's going to be worth 5. I don't have that yet. I will get to that level of specificity at some point. But the way I think about my charter, the way I think about the goal of this demand team that we've put together is we are responsible for leading the market externally with thought leadership, and we're responsible for leading the company internally with the way we think about ourselves, the way we talk about ourselves, the way we present ourselves. What is our narrative? What is our point of view? These things are really, really important. We can't go and create all this pipeline, all this revenue if we're not true industry leaders, true thought leaders. So that dovetails into part two of our mission statement, which is creating and capturing as much demand as possible. We need to create as much awareness as we can so that when the SDR calls that person, they're familiar with ClickUp when the AE is on that call, the prospect has an understanding of what we do. We need to create and capture as much demand as possible. Which segues into part three of our mission statement which is designing and winning the category. We need to think differently about what this category is. That we're in the existing category is not sufficient. Daniel. Like the existing category is called collaborative work management. That's the old way of thinking about how work gets done. Software is converging. AI has unbelievable capabilities, many of that. All of those products and capabilities are baked into ClickUp's platform already. And we need to market to be aware of this new category. So all of these parts of the mission statement are acting in unison and, and it's by unpacking each of them. This is our path to $100 million in incremental revenue. So before I get into. I know I'm like dodging your question answer answering with specificity but I think it's really important that marketing teams have these higher level missions and make sure that they are a leadership function inside of their company. Otherwise you're going to be a ticket taking company. Otherwise you're going to be a support mechanism for the sales team. That's not what we are. We are, we are a leadership function for the market for the company. We're generating as much pipeline as possible and we're winning the category and that is the service that we provide to the company.
Daniel Murray
And I don't think you dodge it. I think we're break going down level by level. So like the high level go billion. The next goal, I need to get 100 million of of that this year because that's the incremental value. How I'm going to do that. I need to make sure we win this category. We're have thought leadership internally and externally. We need to redefine this this category. I mean also the point you made with I see this problem all the time with sales teams is one sales rep has one market, another sales rep has this market. This market has 80% brand awareness. This market has 20% band. This rep is crushing it. That reps not crushing it. And they think it's because of like and it's like actually no, we might need to move some marketing efforts so we can get brand awareness in these markets as well. So to help those reps out. It's not always a rap problem. It could be that there's no awareness in those markets and I see that all the time too. Yeah. So yeah, I mean okay, we'll break the Next goals down, step by step. So I know you're one of your favorite ones. We'll go to your favorite one first. Is like winning the winning a category. You've been talking about this all the time. So how did, how, how do you think about winning category? Like what does it mean to win a category?
Kyle
Yeah, for, for me, it means architecting the future that our customers need to live in. We need to have a point of view that brings to life the current state of the problems that our customers are having and architects the future for what success looks like when you solve these problems. To the extent that we can bring this vision to life now, we have this from to journey, we have this value journey that we can take our customers on. The crisper and clearer we are about this point of view, the more our customers trust us that we understand their universe, the more they're willing to invest in us as partners with them to solve this and help them realize this promised land. So we, the first thing that, one of the first things that I've been working on here, Daniel, is we need to be really crisp about the problem that we solve. If you look across our space, Collaborative Work Management again is the name of the category, the existing category. A lot of it is around productivity, A lot of it is around efficiency. A lot of it is around time savings. And those are all very useful things, of course, but it's not visceral. There's no emotion in any of those problems. You know, Daniel, if I go to you and I say, hey, your team could be 20% more efficient, is that going to get you to leap out of bed? Probably not. And so what is a different way that we could frame the problem and what is a different way that we could present that problem to our customers to get them interested in our point of view, to get them interested in our product. And that's one of the first things that we're starting to do. So how do you do this? It's not an easy thing. We right now we designed a field survey where we asked our 800 customer facing people that exist at ClickUp, we ask them what are the problems that we solve for practitioners? What are the problems that we solve for champion or for executives? Practitioners and executives, we want two different levels because they're very different altitudes. And then the follow on questions are what are the impacts of solving those problems? And we got really unique insights from the hundreds of people internally that contributed to the survey. So that's part one. Ask as many people internally as you can. Part two, I would, right before we started recording this, I was on with one of our best customers and I was asking him the exact same questions. What were the problems before ClickUp? How did you communicate those problems to your executives? What's been the impact now of your multi year engagement with ClickUp? What have we actually made happen for you? And just really try and understand from the fields mouths and from customers mouths, what is the problem that you solve? And then the marketing spin on that is the language that you put around it. How can we make it more emotional? How can we create language that, that we can own? And if we own that language now, we're checking the box of leading the market externally, we're checking the box of leading the company internally with visceral, emotional language that we can craft a story around. And so this is I, I think the tip of the spear. When I think about how am I going to hit my $100 million pipeline number? I need to be different than any of the competitors in the space. I need to think differently about the problems that we solve in the future that we're architecting and the need to take that to market really, really sharply internally across our company, but also externally.
Daniel Murray
Yeah, I mean like just even me thinking about ClickUp as a company, I know ClickUp because I see ClickUp everywhere. I also see some of the competitors a lot too. I kind of know what both of you two do. But I, if you ask me right now like what does the five people do differently or what they solve differently, I probably couldn't give you an succinct answer. Like I could be like, I should maybe try all three of them and see which one works better for my company today. So. But I might go with ClickUp more because I, I ClickUp is out marketing people like these people.
Kyle
And that's the interesting thing about it. And it's something of a counterintuitive thing for many marketers. It's definitely a counterintuitive thing for many product leaders and Many product led CEOs is many people think that marketing your solution is an effective way of marketing feature functions, capabilities and of course to a certain extent you need to do that. I believe, and I learned a lot of this from Christopher Lockhead, who authors who authored Play Bigger and he has a subsack called Category Pirates, that a more effective way of marketing is actually marketing the problem that you solve, evangelizing the problem that you solve because that gives you authenticity and it gives you credibility. And if you're loud and if you understand the problem that your customers are having well enough and you communicate it crisply enough, they will assume that your solution solves that problem. You don't have to be as on the nose about this actual solution and all the bits and bots and features and functions. And so that's what I really want to try and do. And right now as you look across our space, there's nobody in our space is communicating really clearly about this problem. So it's a huge opportunity for us to come in and be thought leaders and show up differently against the rest of the competitive set. And that's something I really want to focus on.
Daniel Murray
One thing I want to get a picture into. So okay, the, the category problem you're going to attack and that's a messaging thing, that's a, like how you like going to change the language on landing pages, on ads, on the way you pitch decks, all that stuff. Part of the things that makes ClickUp so unique too is like there's a PLG motion. There's also like a sales that motion. And you've been in both arenas of PLG and sales that how do you think about those? Like, like what needs to improve in those motions to like get that incremental? Because there is a lot of things that, especially when you're that side, you tweak a one part of the cycle, 3 to 4%. That's, that's millions and millions of dollars. So how do you think about like tweaking the, the processes for like PLG and just like actual like bigger sales deals?
Kyle
Yeah, it's a great question, Daniel. Generally speaking, and this is not true 100 times out of 100, but generally speaking, the PLG motion, the self serve motion is going to be a better fit for smaller accounts, down market accounts. Normally there are companies that are, you know, between under 25 employees, let's say under 50 employees. When you are, when we are selling to larger companies, upmarket companies, thousand, five thousand, ten thousand employees, that's normally a guided sale. And they're very different audiences. The mom and pop shop, super important customers of ours, we have three thousands, tens of thousands of these mom and pop shops who are customers and they're extremely valuable customers of ours. And we take their feedback very seriously. What they need is not necessarily exactly the same as what the 10,000 person enterprise company needs, but there is overlap. They're not totally distinct either. They're trying to manage projects, they're trying to execute projects, they're trying to grow their companies, they're trying to do things, you know, from a strategic level that are more or less the same and therefore top line messaging can often be more similar than different between these two very different audiences. However, the velocity at which we get to the feature level messaging has to be much faster in the down market segment because they care more about the features and the capabilities. That's what they're really investigating versus an enterprise sales led deployment where we're controlling more of a narrative. We're controlling the narrative in a more complex ecosystem that has more competing apps, that has more tools, that has more data, that has more stakeholders. And so we can use a lot of the same messaging. It's a matter of emphasis and it's a matter of speed at which we get to the okay, so what does your product actually do? And we need to do that a lot faster in the PLG motion than we have to do in the sales LED motion.
Daniel Murray
Which makes total sense because one stake, probably one buyer with a credit card PLG where like big enterprise, multiple stakeholders have a procurement, care about security, care about these big problems that you don't even need to think about when you're marketing to a small mom and pop, care about integrations, care about all these things that you don't really care about. So I'm going to talk about the non PLG because you came from the sales background. So I want to talk about what are some things that you're seeing right now or planning on changing and at the size of company you are on to make the sales team more efficient, that you're getting into bigger accounts, that you're winning these deals more effectively. All those things.
Kyle
Yeah. One of the, the main thing, and this is probably the thing I've been able to do most immediately because I'm very passionate about it and I have a lot of experience having done this in the past is we haven't we ClickUp have an unbelievably horizontal platform. If you want to do something on our platform, you can probably bend the platform to your will and do that. And that's very useful of course, and that's why we have such a large PLG motion. However, saying that you're everything to everybody is not always the best marketing strategy because everything to everybody is often nothing to nobody. And so the first thing that we've been doing is we've been quote unquote productizing the platform. What are the top 10 use cases that exist for ClickUp? Many of them are across marketing teams. The way you execute campaigns, the way you do creative production, the way you run your Field events, those types of things. And then of course there's OKRs, corporate initiatives, there's general project management, there's product launches and engineering, there's top 10 use cases. Right? So we're productizing the platform and then we're creating all of the relevant bills of materials for each of those use cases. Pitch decks, demo videos, demo flows, one pagers, thought leadership content, how to oriented blog content, social content, yada yada yada. The bill of materials is very long and then we can architect real demand gen campaigns around each of these use cases. So the first of our campaigns we're doing, it's launching at the end of May around our first use case. And we're showing the company that if we organize the product around these use packaged use cases, we're going to be able to create a type of demand that's going to be more predictable for the sales team to have 10, 20 opportunities that are on the same theme versus bouncing across a bunch of different themes because our platform is so extensible. So we're creating unified demand. And the other useful component of this Daniel, is we're able to integrate AI into these use cases. That lends itself to a different type of product pricing model. So the PLG to SLG motion is very useful that we have internally. But many of our sales led opportunities are anchored to ppu, price per user, packaging or pricing because they come from the PLG universe. Now with this more package use case approach that incorporates AI, we can start using AI as a pricing lever on top of the price per user. How many customized agents are you creating using ClickUp? What does your AI credit consumption look like? Are you using us for connected search? The way that you might use glean, how much AI usage are you going to have and how can that serve as a really useful lever inside of these opportunities that we're generating? So the average deal size we should start to see go up pretty significantly. The value that we're creating we should start to see go up pretty significantly. And that's the first thing that we've really been focused on is what are the most popular use cases and how can we create more of a prescriptive value journey for our customers that show them start here, go here because that's what customers really want and need and that'll really help us increase the demand or the value capture that we get from these appointments.
Daniel Murray
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Kyle
That's right.
Daniel Murray
So it makes makes sense of like breaking down the product and what, what is like the. For people. Like if you're like people who are marketing to everybody right now, like how do you make that decision without also like conflating that you are like. Because the messaging was that you're everything. Now you're going back to saying like, I do this one thing for these people. So how do you like keep topline re. Re messaging that you do a lot of things and then also message that you're also like a real problem that someone's having right now.
Kyle
That's a great question, Daniel. So let's go back what we've talked about. We've talked about top line narrative definition and problem identification and then we've talked about kind of the click down from there, which is the use cases that your platform actually makes possible. And so the hierarchy here as we think about this is when we define the big problem that we solve now, the next thing we need to do is we need to take that problem and we need to extend it into the use case that we bring to life. There should be complete unity and cascading of the messaging from the top line to the next level down. And so we want to make sure that when we're presenting the big problem that we solve, it still is about we can take down all of these various use cases. But most people, Mr. And Mrs. Demand Gen Marketer, are interested in how they execute campaigns using ClickUp. And here's how we do it and here's how we eliminate that pain. And so a lot of it is making sure that there's message resonance from one level to the other and then there's audience segmentation. So this is all about promotion and we're very sharp about who are we promoting this campaign execution use case, who are we promoting it to? Obviously it's marketing stakeholders and probably within marketing stakeholders. We can probably leave creative, you know, design people to the side for the time being. Let's focus on demand gen growth, marketing, revenue marketing. Let's focus on those people. And so segmentation is a big part of it. And then we can try and make sure that when we start to engage the other audience, we're still using the same messaging hierarchy. We're just focused on a different use case.
Daniel Murray
I mean, that totally makes sense. And then the beauty with marketing now is I targeting so good, you could just put a landing page target those people test messaging. But also since you are covering marketing and sales, like what's the difference between like testing messaging at scale with marketing but also like testing messaging with like one to one with sales? Like, because that's another way to test messaging is like these sales reps going, trying new pitches, trying new angles, seeing what works. And you can also cascade that up to like top level. So what's like the difference between those. Those.
Kyle
Yeah, it's such a, such a good question, Daniel. I, I love the concept of field testing. You know, sales Reps using language, SDRs on cold calls using language and getting more qualitative feedback from them. There's kind of two different ways. The traditional means of testing messaging from a marketing standpoint would be like, let's just put the A test and the B test on search engine marketing and just let's see which one converts better. But when you are going through this exercise of problem identification and new language, how they convert from a direct response standpoint is not necessarily always the best way of evaluating whether or not you had message resonance. A lot of that will come from the live conversations that you have. Because what you're trying to do is you're trying to change the way people think. And so there's kind of a couple different things that you're looking for in this field testing. You're looking for when the sales reps are using this language, when SDRs are using the language, you want to see what is the reaction of the person on the other end. Are they, is it resonating? What is their body language? What happens? So that's kind of point number one. When they first are exposed to this new language that you're using, what's the reaction? And the second thing is, does that prospect start using that language? Back to you at the end of the call and I'll give you an example of this, Daniel. When I was at Clary, the problem that we architected at Clary Clary is a forecast, is a forecasting, revenue, intelligence type solution. And the problem that we architected at Clary was this big trillion dollar problem of revenue leak. And so we would present this problem in all of our sales calls and SDR calls and all the rest. And this was not a phrase that had ever been used before, but we would present this problem, hey, we're Clary. We solve revenue leak. It's, you're leaking 15 of your revenue. It's a major problem. And by the end of the call, the prospect would be saying to us, I think we can stop our revenue leak here, here, and here. And we're like, okay, this is working. This is resonating because they're using our language back to us. So it's a little bit of a dark art. It's not nearly as scientific as other types of message testing or AB testing. It's. It requires a different level of conviction from you and like, you as a marketing team and you are you as a leadership team to get this new language of this new framework out there. And then it requires your sales reps to be pretty dynamic on calls and to assess how much of the new language is really resonating.
Daniel Murray
I'll go one step deeper at messaging right now because one thing I want to ask is, because everybody's doing this right now and how you're going to tackle it, everybody seems to have something that's AI powered. Everybody seems like it has AI baked in their product. So how do you win the AI messaging battle when it feels like everybody is saying AI powered AI this AI, that's, um.
Kyle
Yeah.
Daniel Murray
How. How do you think about that?
Kyle
It. It's a focus on real outcomes. Daniel I think a lot of people are burned, have been burned by AI and to the extent that they still trust it, their trust has been really diminished by the poor experience they've had so far. And so as we think about, okay, we're taking ClickUp as A broad platform. Great. We're now architecting the use cases, the most popular use cases that we solve. So campaign execution is one of those use cases. We're embedding our AI capabilities into that use case. So as we demo you how we execute campaigns using ClickUp, we're going to show you. Here's how AI can take the transcript from your marketing kickoff call, your campaign kickoff call, and turn it into a campaign brief. And here is how AI can create the project list for you and auto assign owners. And here is how AI can take the brief and create the promotional emails. And we're actually going to show you that this is not just smoke and mirrors. This is AI that's embedded into these workflows automatically. It doesn't require your team to be prompt engineers, it doesn't require you to do any heavy lifting. All you need to do is press go and the rest is just going to happen in the background. And we do that by showing and not by telling. So I think people are pretty jaded by a lot of AI messaging right now. We're not going to lean too heavily into saying we're the best AI company of all time because like it's going to be in one year and out the other for the majority of the market. But at the same time we need to show that we are leaders in AI and we're showing that we're leaders by the outcomes that we're producing in these use cases that we're architecting.
Daniel Murray
One thing also, I know that ClickUp is very good at doing, is like doing things differently, like standing out in marketing with like their social, with messaging, with doing testing. So what are some things that you're like, what are some freedoms that you're having right now that you are thinking about to take like some risks that you haven't taken before to like get to that hundred million goal?
Kyle
Yeah, there are 10 corporate values at ClickUp and I'm not going to swear on this family podcast, but one of them is literally normal effing sucks. And it says the F word on the new hire onboarding slide like normal effing sucks. And I was like, okay, this is a serious thing that, like this, it's, it's, it, it matters, Daniel, because that gives the company and gives me free reign to think very differently. And we don't want to be boxed in and we don't want to be super buttoned up, corporate IBM type marketing like we had before. I was here, I think at Dreamforce last year or the year before. We had protesters protesting Slack and that was how we promoted our chat offering that's now part of our platform. Like picketing Slack outside of Salesforce HQ at Dreamforce. Like is that kind of thing that like the precedent is set for us to be very creative, to go outside of the box, to not be normal. So I don't know exactly how that's going to manifest, but I know that in the meetings that I've had and the brainstorms that we've had, the creativity is off the charts because people are not afraid to paint outside the lines and to take some risks. And you have to. And you have to to stick out, especially in this day and age. So I don't know what that means exactly, but expect more of the same.
Daniel Murray
Yeah, I just wanted to say that because I think going back to our first, we started with big goal, but it also starts with the values that the company has instilled into the people. One leadership being willing to have people take big risks. And also they know that when they have big goals you're not going to get that through doing the, the basic playbook that other companies are running. Because if it is a playbook, then someone's ready, probably executed it before. That's right. So yeah, it's cool because you're in a stage right now where four weeks in you have unlimited rain to think and try new things and don't know what I'm going to do yet. But right now, the first six weeks is what you're saying. I got to figure out what the sales team's doing, how our customers are saying, how amazing. And I bet you even when you did the exercise talking to all your frontline salespeople, there's a range of what people are saying differently to the customer that could be reeled in to like clear assistant messaging as well.
Kyle
100% huge variance by region, by segment, by role, all the rest. So it's no small feat to be the organizing principle that summarizes all of this thinking and all the different avenues that we can go to explain our value. But when we get it right and we can communicate really crisply, it unlocks everything else downstream.
Daniel Murray
So we talked about the messaging, the messaging to win the category. We talked about a little bit about the sales and PLG motion. How you thinking about that? Is there any other things that you are thinking about like high level goals that you need to execute to like get 100 million? Because 100 million is a huge number. Like some companies don't even do 100 million. So most companies don't do 100 million. So it's a big number for a marketing leader to add 100 million.
Kyle
Yeah. Yes. The answer is there's a million. Well, I shouldn't say mil. There are definite levers that we can pull and we are blessed by this super high velocity product. LED motion like the inbound demand that we have is pretty, pretty remarkable. Now one of the main things that I need to do is I need to, I'm running a program that we're calling no Lead Left Behind. I need to make sure that every single lead that comes into whatever funnel they're coming into gets the exact right context messaging, treatment, follow up, etc. So that we can capture every single drop of revenue. And if we pipeline, if we don't do that, there's no chance that I have to reach that 100 million target. So maximizing and optimizing all of our inbound lead funnels, our SDR team, our lead routing, our lead scoring, our prioritization, the AI that we're using across the whole thing, like that's an enormous part of it. A lot of, a lot of folks will think of that as demand capture. And I think it's really, really important that you are super tight, airtight on all those various channels of demand capture. So that's one thing. The second is how are we taking these use cases to market? What are the demand campaigns that we're doing, what are the outbound plays that we're running, what are the other signals that we're using to prioritize which accounts and what kind of segmentation we do for these various use cases? So I need to figure out what this entire mix looks like. But there's probably, you know, the top five or 10 things, levers that we can pull that are going to make an outsized difference here. And I, I don't have it exactly figured out yet. I don't have it totally line itemed out yet. But by the end of my second month, by the end of June, you better believe that we're going to be pretty airtight and this ship is going to be moving in the right direction.
Daniel Murray
Yeah, usually what I've seen when you're at a high revenue, because I've been at a SaaS company that was doing hundreds of millions in revenue and usually what the, what you're trying to do is like make sure systems processes funnel is efficient. Now like can we raise like lead to OP just by this much by changing this to increase that metric or is it, do we see a leak of like, when leads come in that they don't get a quicker time to touch or the met. Like, these people are messaging, right? It's usually just like a levers in this whole, like, scalability of like. Because what worked, like you said at the beginning, what worked before, where a lead comes in, they say certain things, they close. Now there's more competition, there's more, there's more people. And scaling people is one of the hardest things to do, especially with sales. So it's like usually like a efficiency play as much as like a big play on like demand and messaging change, but it's also a big efficiency play as well.
Kyle
Definitely, yes. And we need to be really sharp about every single conversion point in the funnel from lead to meeting and then meeting to op and op to close and everything in between. So you're spot on about that. Daniel. The thing that I'm trying to do and what the energy that I'm trying to bring is to think differently about the type of demand that we create. Right now, we do very well at the PLG to slg kind of taking that PLG motion and it's informing our sales LED funnel. How can we create a totally different funnel for our sales team? How can we create a totally different type of demand? How can we engage a different audience, a more senior level audience? Because frankly, many of the folks that come to us in the PLG motion are practitioner level, they're lower level. So how can we engage a CMO instead of the content marketing manager? And if we can figure out the right way to do that, we can accelerate deal cycles, we can create larger deals because we can attach to more use cases. And if we can unlock that and start that boulder rolling downhill, that's going to be super value accretive to the customer as well as to us as a business. So that's the other side of the coin that I'm trying to figure out operationally.
Daniel Murray
Two more questions. Before you said you got hired because you need create an incremental like 100 million. What do you know that you know is efficient right now? That like, you, you don't have to touch like. Or is creating that, that revenue that's going to be like, consistent and you know that's coming in like, does that like, sway your focus somewhere else? Like, you know that this part is just a machine. I don't need to touch it. Is it that PLG motion you just talked about? Is it like, what is the machine?
Kyle
It's the PLG motion for sure, Daniel. And then in Our smaller segments. What's, what is very well instrumented right now is we have product usage signals that will be served up to the reps, our sales reps and our sales reps will take those usage signals. There are five people using ClickUp in this workspace or they are using these five different products in the last seven days or you know, a million different product signals that we can rise up to our reps and then our reps are prioritizing accounts and going to find the upsell opportunities there. That's working exceptionally well. So we don't, I don't have to worry too much about that entire universe of product signal and there's some programmatic things that we can do and there's some AI things that we can do to sharpen it. But it's not necessarily my biggest focus. My biggest focus as I mentioned before, is what is a new different type of demand that we can create. What's a new type of sale that we can architect that leans more into our AI capabilities for these various use cases that we have and just commands a different price and a different value because it's more prescriptive and it's more of a painkiller for the things that matter more to executive level stakeholders.
Daniel Murray
Yeah. So if I getting this correct, your goal is ClickUp really wins on SMB. Now we need to win how we went up market. We need to start going click like mid market enterprise. Like those are like, which is a, like you said before, different messaging, different motion, different type of people, different stakeholders. And also some of those, what you said before, some of those like SMB are becoming mid market and like how do we get them from, how do we help them get to mid market to those mid market to enterprise or we have the right signal. So it's, it's more of a how we go up market which is easier to go. To be honest, it's easier to go up than down. As I've seen before in, in, in most companies it's like way easy to go up.
Kyle
I think so too. We'll find out.
Daniel Murray
We'll find out. It's your problem to deal with right now. But lastly, what is a, a marketing hill you would die on?
Kyle
Oh, good question. AI is not the answer for everything. And I say this, there's a lot of momentum out there and if you go down LinkedIn for five seconds and you'll see some sort of AI tool or tip or manifesto or whatever and I think that marketing people feel a lot of understandably feel a lot of Pressure to become AI native. And I think it's very important that you understand what AI is and isn't good at, what AI is not good at. And I think what a lot of marketers have seen started or a lot of the expectation that companies have for how marketing uses AI is to do strategic thinking. Now, AI right now is not good at strategic thinking by definition. Daniel like these AI models have been trained on historical stuff like what's happened in the past. AI can't do this strategic thinking to invent a different future for your customers. That has to come from you. It has to come from human strategists that are connecting a different set of dots and the, the marketers that understand this, that use AI to open up more time and capacity for strategic thinking for themselves. These are the marketers that are winning. The marketers that are trying to outsource everything to AI and just, you know, have an AI content marketer, an AI campaign manager and AI, all this, like, it's just not going to work that way. So I, I, I will die on this hill. I've seen both models in action. I've seen the right marketers do extremely well by integrating AI. And I've seen marketers completely crash and burn because they expect too much or try and outsource too much. So find the right balance.
Daniel Murray
I mean, the type of thinking that AI could do everything is a type of thinking of you are going to get replaced if you, if you think AI could do everything. Very true. Which is so I do agree like this, what, what wins for, for humans is like our creativity, our different inputs are like, we don't take only inputs from marketers, we take inputs of different industries, different things people are doing. Like you could take AI and say, tell me what like Nike strategy doing. But if you try to do like a startup they've never heard of and try to ask them like how they're doing things that AI is not figuring it out. You're going to have to figure it out yourself. So it's like, it's really good at like broad thinking but not like intense focus strategic thinking like you said. Lastly, where can people find you and.
Kyle
What you're doing on LinkedIn? I post relatively regularly on LinkedIn. It's been a little hectic here as I've ramped up. So I've dialed my LinkedIn stuff down, but come connect on LinkedIn, say hello, that'd be awesome. And then if you want to learn more about ClickUp, it's just ClickUp.com we got everything you need there.
Daniel Murray
Cool. Thank you so much. I appreciate you coming on.
Kyle
Always a pleasure Daniel.
Daniel Murray
Thanks so much for listening. Keep tuning in to hear more great insights from the coolest marketers from around the world. If you haven't already, make sure to subscribe and follow the Marketing Millennials podcast on Apple Podcasts, Spotify, YouTube or wherever you get your podcast. And if you like what you hear, I would greatly appreciate you giving us a five star rating. It helps bring more marketers into our community.
Kyle
Sam.
Podcast: The Marketing Millennials
Host: Daniel Murray
Guest: Kyle Coleman, Global VP of Marketing at ClickUp
Release Date: June 27, 2025
In Episode 329 of The Marketing Millennials, host Daniel Murray engages in a deep conversation with Kyle Coleman, the Global VP of Marketing at ClickUp. The discussion revolves around building a winning marketing playbook, setting ambitious goals, and innovating marketing strategies to achieve $1 billion in Annual Recurring Revenue (ARR). True to the podcast’s ethos, Kyle shares actionable insights and real stories from his experience leading marketing teams at a high-growth software company.
Kyle Coleman provides an overview of his journey to becoming ClickUp's Global VP of Marketing. Starting his tech career as a Sales Development Representative (SDR), Kyle transitioned into leading large SDR teams and eventually gravitated toward marketing. His passion lies in broadcasting company messages broadly and driving pipeline growth, which has led him to serve as Chief Marketing Officer (CMO) twice.
Kyle [01:26]: "I've been a CMO twice now because I care about broadcasting messages as broadly as possible and... the impact that marketing teams can make in doing both of those things."
Daniel introduces the primary focus of the episode: ClickUp's ambitious goal of reaching $1 billion in ARR. Kyle explains that while the number is somewhat arbitrary, it serves as a rallying point to drive the company toward becoming an enduring, legendary organization fit for public markets.
Kyle [03:00]: "The high level goal is to get to a billion dollars in ARR... it's shorthand for all the other supporting goals that we have."
Kyle delves into the specifics of achieving the $1 billion ARR target by focusing on incremental pipeline generation. He emphasizes the importance of marketing as a leadership function within the company, responsible for thought leadership, demand creation, and category definition.
Kyle [05:41]: "We are a leadership function for the market for the company. We're generating as much pipeline as possible and we're winning the category."
A significant portion of the conversation centers on defining and winning a new category in the market. Kyle outlines the necessity of architecting a future that aligns with customer needs and differentiates ClickUp from competitors. He highlights the process of redefining the problem ClickUp solves in a more emotional and visceral manner to resonate deeply with customers.
Kyle [09:57]: "For me, it means architecting the future that our customers need to live in... the more we're clear about this point of view, the more our customers trust us."
Kyle discusses ClickUp's strategy to "productize" their platform by identifying the top use cases and creating tailored materials for each. This approach aims to generate more predictable and unified demand, facilitating larger and more consistent deals. Additionally, he touches on integrating AI capabilities into these use cases to enhance product pricing models and deal sizes.
Kyle [17:44]: "We're creating all of the relevant bills of materials for each of these use cases... to create a type of demand that's more predictable for the sales team."
The conversation shifts to refining ClickUp’s messaging to emphasize the problems they solve rather than just their features. Kyle emphasizes the importance of authenticity and credibility in marketing, arguing that leading with the problem statement can position ClickUp as a thought leader. He also discusses the strategic use of AI, highlighting how ClickUp embeds AI into workflows to deliver tangible outcomes without overreliance on AI hype.
Kyle [28:42]: "We're embedding our AI capabilities into that use case... showing that we are leaders by the outcomes that we're producing."
Kyle explains the distinction between Product-Led Growth (PLG) and Sales-Led Growth (SLG) motions at ClickUp. He details how PLG targets smaller, down-market accounts with rapid feature-level messaging, while SLG focuses on larger, upmarket enterprises with a controlled narrative. The integration of AI into sales practices aims to enhance deal sizes and accelerate sales cycles by addressing executive-level pain points.
Kyle [36:56]: "We need to think differently about the type of demand that we create... engage a CMO instead of the content marketing manager."
Kyle outlines strategies to maximize demand capture, including tightening lead funnels, optimizing lead scoring, and ensuring every lead receives appropriate follow-up. He emphasizes the importance of operational efficiency in transforming inbound leads into significant revenue, ensuring no lead is left behind.
Kyle [34:04]: "We need to be really sharp about every single conversion point in the funnel from lead to meeting... it's going to unlock everything else downstream."
Highlighting ClickUp’s corporate culture, Kyle mentions the company’s value of "normal effing sucks," which fosters an environment of creativity and risk-taking. This culture encourages unconventional marketing strategies and out-of-the-box thinking essential for achieving their ambitious growth targets.
Kyle [30:41]: "We have free reign to think very differently... creativity is off the charts because people are not afraid to paint outside the lines."
Kyle shares his firm stance on the role of AI in marketing. While recognizing AI's potential, he warns against over-reliance, emphasizing that AI cannot replace strategic thinking. Instead, marketers should leverage AI to enhance their strategic capabilities, not outsource them.
Kyle [40:47]: "AI is not the answer for everything... marketers should use AI to open up more time for strategic thinking."
The episode wraps up with Daniel and Kyle summarizing key insights. Kyle encourages listeners to connect on LinkedIn and explore ClickUp for more information. The discussion underscores the balance between leveraging technology and maintaining human strategic input to drive marketing success.
Kyle [43:24]: "Always a pleasure Daniel."
Kyle [01:26]: "I've been a CMO twice now because I care about broadcasting messages as broadly as possible and... the impact that marketing teams can make in doing both of those things."
Kyle [03:00]: "The high level goal is to get to a billion dollars in ARR... it's shorthand for all the other supporting goals that we have."
Kyle [05:41]: "We are a leadership function for the market for the company. We're generating as much pipeline as possible and we're winning the category."
Kyle [09:57]: "For me, it means architecting the future that our customers need to live in... the more we're clear about this point of view, the more our customers trust us."
Kyle [17:44]: "We're creating all of the relevant bills of materials for each of these use cases... to create a type of demand that's more predictable for the sales team."
Kyle [28:42]: "We're embedding our AI capabilities into that use case... showing that we are leaders by the outcomes that we're producing."
Kyle [36:56]: "We need to think differently about the type of demand that we create... engage a CMO instead of the content marketing manager."
Kyle [40:47]: "AI is not the answer for everything... marketers should use AI to open up more time for strategic thinking."
Kyle Coleman's insights offer a roadmap for marketing leaders aiming to achieve exponential growth through strategic goal setting, innovative category definition, productization of offerings, and balanced integration of AI. ClickUp's approach demonstrates the importance of aligning marketing strategies with overarching business objectives, fostering a culture of creativity, and leveraging technology to enhance, rather than replace, human ingenuity.
For more insights and actionable marketing strategies, tune into The Marketing Millennials and join the community of forward-thinking marketers.
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