The Best of Both Worlds: How PLG and SLG Win Together with Gaurav Agarwal and Kyle Coleman of ClickUp | Ep. 371

0:01Kyle Coleman:If you ever wished you can clone yourself at work, meet Optimizely Opal. It has out-of-the-box AI agents that learn your brand, plug into your existing stack, and automate your work that used to take weeks. Requests, revisions, approvals, all of it, poof. See it at Optimizely.com slash AI.

0:26Kyle Coleman:What is up? We're back to the Market Millennials podcast. and I am doing another special episode with you and dropping one of the best sessions at Marketing Land Festival 2025. It features two absolute operators, Kyle Coleman, Global VP of Marketing at ClickUp, and one of the sharpest guys in B2B right now, and Gwarov, COO of ClickUp. He is leading all things revenue across both product-led and sales-led growth. And in this episode today, they break down why product-led growth and sale-led growth is a false choice, how to actually measure incrementality, how demand creation and demand capture work together, why messaging consistency is a superpower, and how AI is changing both motions for good.

1:24it's one of the most tactical episodes you'll hear and it's backed by real operator wisdom.

1:32Kyle Coleman:Okay, let's get into it. And if you want more sessions and see sessions from Marketing Land Festival 2025, you can come into the Marketing Land community or we're also launching Marketing Land 2026 soon, but you can register in the community as well. Okay, into the episode. Bye. 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 guests, stories or it didn't happen. Get ready to turn the f*** up. All right. Hello, everybody. Welcome to this session at Marketing Land.

2:23Kyle Coleman:We're in the growth stage. We're very excited to be talking about a topic that is near and dear to both mine and Garof's heart here, which is the best of both worlds. How does product-led growth and sales-led growth win together? We're going to dive deep into these topics. Before we do, though, let's start with a couple intros so that you all know why you should be listening to us. We have some things to say, and we want to establish a little credibility first. So, Garof, who are you? What do you do? Thanks, Kyle. Thanks. Thanks for kicking us off. So hello, everyone. I'm Gaurav. I'm the Chief Operating Officer at ClickUp, responsible for all things revenue across PLG and SLG.

2:56Hence, we are here to share some learnings that we have had. Kyle, back to you. Beautiful.

3:01Kyle Coleman:And I'm Kyle Coleman. I'm a global VP of marketing here at ClickUp. I'm more focused on the sales-led side. But as you will come to learn, the PLG and SLG motions at ClickUp are inextricably linked. We can't really do one without the other and vice versa. And so, you know, my purview is mostly focusing on the demand programs, sales development programs, sales programs that are driving our sales led motion. But there are so many tentacles into and across the aisle for our entire PLG engine that it's been very interesting for us to unpack all of that. So let's dive in. Gaurav, you've been here now at ClickUp for three, four years.

3:38Kyle Coleman:How long have you been here? About four years now, getting to four years. Yeah. Yeah. How do you decide? You have a finite budget. you have to make a decision about what to invest in, what teams to grow, what programs to grow. How do you decide whether you're going to build a PLG engine or build a sales led engine? What goes through your mind? It's the favorite word I have, right? Incrementality. There's a running joke internally that we, me and Kyle have in ClickUp, like what's Gaurav's favorite word? It's incrementality. But to sincerely answer your question, Kyle, I think it comes down to a lot of the world phrase PLG and SLG as if you have to do one of them, you can't do both.

4:17And I think that's the wrong way to look at it the same way as commercial versus upmarket is the wrong way to look at it. These are all false dichotomies that people create. The way to look at this is, you know what, try to do a little bit of both. Of course, there's constraints now. A lot depends on your business model as well. does your business model support if you have a large tam potentially plg would work but if you're only selling to top 100 companies out there perhaps plg is not a thing for you right so there are clear business limitations across which one should apply more than the other but outside of that assuming you're running a software business that has a few million people that can use the product your price points can range from 10 grand to say 100 grand to a million if you have all that breadth in business then you could argue that you could make both work so do not fall into that false dichotomy what's more important is you try both of them see what is truly incremental to the business what i mean by that is if i put a dollar here do i get an roi can i attribute attribution is a sinful word let's not use the word attribution but can i directionally measure and say that if i put a dollar here i perhaps i'm getting two dollars back.

5:28If yes, then yeah, keep putting the dollar there because as executives in a startup, our goal is to find opportunities where we can make investments such that those investments return back at a very healthy level. So that's the game we are in. It's managing a portfolio and you should be managing both PLG and SLG and making investments based on the ROI that you're getting or the incremental lift to the business based on the investment made.

5:55Kyle Coleman:Love that. And I know another way that you've thought about it, I've heard you speak about this, and this really resonates with me for a variety of reasons, is that it's not necessarily PLG versus SLG, again, a false dichotomy, as you mentioned. It's more about what are the things that we're doing to create demand and what are the things that we're doing to capture demand or harvest that demand. Talk us through, well, what do you mean by that? That demand creation, demand capture, how does that mental model work? That's a great question, Kyle. I think that's I think that's the crux of all of this.

6:26When I say demand creation, what I mean by that is, can you go out in the market and for someone who doesn't know about you, create an intent and a desire to talk to you and seriously consider your product, right? So that's demand creation. And then there's demand harvesting that, hey, I need your product. How do I buy? And interestingly, you can apply sales on both. For example, sales can go like great sellers know how to create demand, they can go spend time with your buyers in those customer accounts, understand their pain point, and tell them about the art of possible and create demand. But sales can also be order takers on the other side where a hand raiser comes in that's extremely high intent.

7:09And now what you're doing is you're running a great deal and you're servicing that customer and ensuring that they have what they need. Similarly, on the PLG side, you could either just be harvesting demand created by sales and now the customer is transacting through self-serve or you could be creating demand run some amazing top of the funnel marketing people are using a product to further deepen their intent and now they are raising their hand that sales can fulfill so you're 100 right the way to look at this is what is creating demand and what is harvesting demand and in any revenue machine creating demand is significantly harder than harvesting demand so that's what this comes down to and you have to be able to do both in a in a way that the net economics of your business work out on this point how have you seen like sales because you come from that world right but at the same time you're one of the few leaders who i admire so much that you grew up on the sales side but then moved to the marketing side how do you see this interplay between demand creation and demand harvesting happening, especially as you move to more sales heavy motions?

8:19Kyle Coleman:Yeah, it's a great question, Garvin. It's something I've spent a lot of time not just thinking about and training teams against, but also actioning in real life. And it's part of the reason why, as you mentioned, I cut my teeth and grew up through sales and sales development and have, for that reason, a pretty unique perspective on what it takes to be an effective marketer with respect to demand generation in particular. And a lot of it, I'm sure many people have heard that it, I think maybe, you know, 10 years ago, it took seven touches for something to stick in somebody's mind. You have to see a brand or hear the value prop or see the commercial, the billboard, whatever, seven times before that brand has really stuck with you.

8:56Kyle Coleman:That was 10 years ago. That was 15 years ago. Now we are inundated every single day. God knows how many ads and banners and messages and commercials and podcast interruptions and all the rest. It's like, it's so hard to keep track. I would not be at all surprised if that number has doubled from it used to take seven touches. Now it takes 15 touches, 20 touches to create that demand. So how do you do that? You need to have not just, um, some sort of presence across so many different channels, outbound ads, hopefully PLG, um, all these different channels, but you need consistency in what you're saying.

9:33Kyle Coleman:You need consistency with what people think about You need a brand promise that is consistent and deliverable across all these different channels, because that is what will ultimately create that demand. And so in the past, prior to joining ClickUp, I had built that engine through sweat and tears and really without any product help, frankly. Like we had kind of, at my previous company, we had kind of a PLG motion, but we kind of sunset it. At other companies, I built the demand engine at Looker and then again at Clary, and there was no PLG component at all. So building that brand awareness, building that demand creation muscle was brute force.

10:12Kyle Coleman:It was outbound emails. It was executive touch points. It was VIP dinners. It was trade shows. It was all of the things that you need to do. And now what's been so interesting about being at ClickUp is I've understood that PLG is just another channel to add into that mix. And it makes that mixture of channels so much more effective because you get a totally different delivery of that brand promise. And so I'm starting to see the universes come together and starting to see how this PLG plus SLG can work really well together. Yeah, I mean, I think you're 100 % right. Because ultimately what both these channels need is very strong messaging that can move the hearts and minds of your users and your prospects.

10:54And you're 100 % right. Like the right teams know how to come up with messaging, both at the user level and the buyer level, and use that central platform that can scale across different levels in the organization. But it's still that same messaging. And instead of making it early on when I had just joined ClickUp, there was just so much divide that there was a camp of people that felt like this is very PLG message. We used to have this message called one app to rule them all. and and and a few a few people have had very strong povs that that message does not work on the sales side of the house because sellers don't want that although that's not true now if you look at what's happening then their marketing is going through consolidation our buyers love us we are talking we are you know this like you are championing some of this guy we have millions of dollars in active pipeline today that is all built on like consolidating the ai sprawl and and and moving moving people away from like having to buy 10 different AI tools to just buying one.

11:54So consolidation, removing sprawl is a very clear strategy. And again, as you said, right, like people end up thinking about it too tactically versus going deep. And if you go deep, you'll find that there's enough messaging that you can come up with that can work for both. And now both the motions are compounding versus taking away from each other.

12:13Kyle Coleman:That's right. And I'm really glad you said that because I think a really important frame for the people that are listening to this really focus on marketing, really focus on growth, is there's this tried and true and potentially another false piece of logic here that PLG marketing has to be feature focused. And what's really interesting and the evolution I think we've been on is to say, well, what if we borrowed some best practices from B2B marketing and started evangelizing the problem that we solve a little bit more and then just let the product speak for itself with how it actually solves it in the product experience that people have?

12:48Kyle Coleman:So if we're more forward and more consistent with this concept of sprawl, the AI sprawl that we solve, this work sprawl that we solve, if we're consistent with that messaging across all the different entry points that we have, and we're getting people into the product, seeing is believing. We want to show them how our product can solve that problem of sprawl in the way that we get them onboard and new user onboarding and all the rest. And so I think that you can be really creative and you can approach things differently by focusing on the problem that you solve, evangelizing that problem. That works very well for an enterprise kind of tops down sale.

13:23Kyle Coleman:And I think the same thing can be true for a bottoms up PLG sort of sale. It just requires you to think differently and to take different bets. You know, this is interesting. the ultimate uh if you look at plg companies who are the ultimate examples of that consumer companies right like a shampoo company a soap company they're all plg company because they're all product-led growth the interesting thing about those companies is when the product is commoditized which is where software is headed you don't you don't sell a soap because of the size of the bar you sell because of a bigger brand theme that you create around it because it's brand affinity that invites people so to your point that you said right like features matter yes but how do you build that brand around your product so people feel inspired and they want to associate with you i think that's ultimately what drives to more true more in consumer marketing in fact i would say brand is a much bigger more in consumer than it has been even in b2b and that plays up over and over again.

14:26So you're spot on that finding those anchor points in bigger problems that we solve in bigger solutions, how you carry yourself, all those are extremely important things for any brand to nail. In fact, more and more B2B brands would begin to do that.

14:40Kyle Coleman:I think that's right. And it's really interesting that both work, like you can go the problem evangelism and we solve this problem route, or you can go some more feature oriented route. And like insurance companies are another great example of this. So we have Geico that's 15 minutes could save you 15 % or more very feature focused. And then we have all state the masters of mayhem. The mayhem is the big problem. They're, they're evangelizing. If you go with all state, you're going to solve this mayhem problem. Those are the opposite ends of the spectrum. They both work, but what do they both do?

15:09Kyle Coleman:They are, they have been consistent on this message for years. And well, maybe Geico has gone a little far astray, but like they were consistent for years and years and years and years. And I think that's really what it's all about. You're trying to own that property in the brains of so many people that you're trying to influence. And that's what effective marketing is. It compels people to take some sort of action. And now as I layer in the PLG component here in the old world, prior to my having a PLG product to sell, my call to action would always be talk to a salesperson. And guess what? People don't want to do as much right now.

15:42Kyle Coleman:They don't want to talk to salespeople. They want to educate. They want to get their hands dirty. They want to play around. So now I have different arrows in my quiver for, from a calls to action standpoint, as I'm educating, as I'm owning this real estate in people's minds, as I'm compelling them to take action, we can go down the more traditional B2B talk to sales route, or we can go get started. Jump in now, use this template. Here's this AI agent you can use. Go get your hands dirty. We'll be here when you need us, but go try this. We know you're going to love it. And so you get, we click up, we have optionality.

16:13Kyle Coleman:And now this is very important. And this is a question I'll throw back to you, Gaurav. Our go-to-market motion can only be as strong as our product. And if we're making this promise that we have the agent, we have the template, we have the workflow library, and then they get into the product and it sucks, that's not good. That's not going to drive any revenue. So how do you think about that product experience and how do you work cross-functionally with the product team to deliver on that? So ultimately, all marketing can do is pour some gasoline on the fire, right? Like we are, the only true mode that exists is product and then marketing can build a brand mode and a distribution mode around it.

16:49So I think that's something for all of us to acknowledge that if you're stuck in a place where product is not good, you shouldn't be there because you don't want to be the person that's overselling a dream. So done. Now, going back to the example that you said, right? Like we will do some messaging at the top. People will have an inspiration to come try something. Previously, they'll go to the sales team and then sales team would provision the product for them. now they go to the plg side i think what happens is your core product has to be good in both cases but when you send people directly on the on the plg side a lot of the adjacent areas around how the product is experienced onboarding sign up activation ux ux becomes incredibly important because unlike a sales-led growth funnel you don't have a human a success person teaching you every step of the way on how to use the product so the product has to be extremely intuitive and we are so lucky for that to be one of the strongest pillars in our product team in click up in fact ux is perhaps the most important pillar in our product framing philosophy because we look at everything from a perspective of how does this make the user experience and and i think that's what you have to prioritize over and over again and you have to track your metrics and you have to see when we ship this are more people getting to this feature are they finding value is that activity translating to economic value towards the end but you have to obsess about every tiny detail on the user experience and i think that's what we do really really well the amount of obsession i see on every small detail the level of user research that we do surveys nps we do a lot of work not just around building the product but around wrapping the product in a way that people can use it.

18:35And if you don't have that, you will struggle to build a very strong PLG funnel. And by the way, we talk about it as if this is just in context of B2B. Actually, that's not true. 20 years ago, Amazon started e-commerce. People were shopping in retail and Amazon was like, we need to digitize commerce. What is PLG? PLG in a way is digitizing commerce. That happened in e-commerce, in retail. Then more recently, in the last decade, you've seen that happen in fintech. people are buying million dollar mortgages directly online with very little human touch like think about it like why do you think your ten thousand dollar software or your fifty thousand dollar software matters more than a person's like an entire life's work oftentimes it's buying a house people are doing those decisions online so previously used to buy low the way you would get a loan is you would call a loan officer and you would did a rocket mortgage would call you back and now you'll go to lengthy two and froze over the phone call and you'll try to get to a place that makes sense.

19:37Now you can do all of that online. So digitization of FinTech happened in the last decade. And that is the journey we are going through right now. And whenever that happens, you need very strong product thinkers and of course, marketing and growth thinkers to think through how the experience would be, but very strong product thinkers that can reimagine what the user experience of that product should be.

20:00Kyle Coleman:Yeah, and that's a really good segue. into this whole concept of AI. I feel like a lot of people expect just to slap AI onto their logo and say, all right, we've created a new demand funnel here. People are, this is gonna be irresistible now. We used to be Acme and now we're Acme AI and the pipeline is just gonna come pouring in. The new users are gonna come pouring in. But ultimately what ends up happening is you make another bad brand promise. And if you just slap AI onto your logo or if you just are blasé about your AI capabilities, or if you expect people to get in and just figure it out, you're creating a really bad experience that's going to end up hurting your PLG funnel and your SLG funnel.

20:44Kyle Coleman:So how do you think about that when it comes to ClickUp's AI capabilities, the agents, the workflows, the dashboards, the things that we have that our customers are relying on to execute core parts of their day-to-day? How do you think about delivering those AI capabilities in that same intuitive way that's powerful while still easy to use?

21:27Kyle Coleman:Optimizely OPPO learns your brand, plugs into your existing tools, and can automate personalization, compliance, reporting, and way more. See what it could take off your plate at optimizely.com.ai. I think it comes down to you have to make it super easy for people to try it out and feel like they are co-building that experience with you and the product.

21:51You can't go to a place where you say, we have done it all for you. Just come and click one thing and start using it. I think that's a great vision to have. But you know what's even more powerful when you do it 90 % of the way there, but you invite some participation from your users so they feel like they have a strong voice in how they want to set it up. And that goes a long, long way because they feel like there's some buy-in from them in how it was deployed. So I think that's going to be extremely important for these AI native features that, yes, you want to get as close to the finish line as possible, but you want to keep a little bit of room.

22:24Maybe it's just clicking a button, but some room out there. The other reason to do that is AI is not fail-proof. AI will fail. So you don't want to build a brand around this thing that, hey, we get 100 % of the things right 100 % of the time. That will backfire. So the more collaborative that experience can be, that's why we strongly believe that AI will not replace human, AI will augment human. AI will multiply human capacity, which means you still need a human in the loop. And I think it's that co-creation between AI and humans that will create magic versus someone just saying, I have the best AI product.

22:58No, I have the best AI platform on which humans can work. I have this question for you, Kyle. Like you've been leading the charge on like AI first marketing for a while now. You did that. I mean, in some aspects at Clary. Clary had a lot of like features ahead of its time than you did at Copy AI. Now you're doing it at ClickUp. How have you seen that problem being solved?

23:18Kyle Coleman:It's a really interesting question, Garavan. It's a tough problem to solve because the inclination that we, especially from a marketing standpoint, have is to talk about how easy everything is to do. But the problem is if something is very easy to do and the expectation is I just click to install and now I can use it, it's probably not going to be customized. And what people are realizing now with these AI solutions is that they have to be customized. Otherwise, the outputs are generic and unusable. And so how do you find the right promise to make to somebody? And how do you make it as easy as possible for them to give the inputs that they need, collect the intake that you need to collect in order to create something that genuinely is usable for them from an output standpoint.

24:01Kyle Coleman:So you have to set the right expectations up front. And we have to lean into a lot of what you're just talking about. The power here is its customization. And we're not it doesn't require you to be a technical whiz or prompting expert or PhD AI person. All you need to know, in the case of ClickUp is you need to be an expert on your domain, on your processes? How do you get not from A to B, that's easy. How do you get from A to Z? What are all the steps that is required to run that process? Where are the areas of friction when you're running that process? Okay, great. Now we have an understanding of the process you want to codify.

24:38Kyle Coleman:And now we can go and replicate that with an AI agent, you can go and replicate that with an AI agent with our agent builder. And so we help people understand that this is not something that you snap your fingers. Because when you've used a tool like that, you go into chat GPT, write me a blog post, and the blog post sucks, because of course it does, because you tried to just go in and skip the hard work. We've tried to make it clear to people that in the clearer and understanding the stronger perspective you have on what good looks like, the more useful our software is going to be to help create that outcome for you.

25:12Kyle Coleman:And so we try and be honest. I mean, if you try and trick people into getting them into the funnel, they're going to be disappointed. So be honest upfront, make sure you're emphasizing what you're really great at. Make sure you're emphasizing that this is still a human first exercise. And we're not outsourcing your thinking, we're codifying your thinking to create great outputs. Yeah, I mean, and I think we're coming up on time, but maybe that's a great way to finish, right? That marketing's job isn't to just deliver boilerplate messaging at the top and be like, hey, this is one all be all. I think it's our job to then come up with highly context messaging that is relevant to people and product experiences that is relevant to people and that can drive them to action.