Beyond Social

How ClickUp Went From Unknown Startup to $300M ARR

• Vista Social • Episode 51

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ClickUp scaled to $300M ARR in one of the most competitive SaaS categories in the world.

In this episode, Reggie and Vitaly sit down with Chris Cunningham, Head of Social at ClickUp, to break down the SaaS growth strategy behind ClickUp’s rise — from living in a startup house to becoming a category leader in the project management space.

They unpack what it really takes to scale a B2B SaaS company in a saturated market: scrappy go-to-market tactics, early product-market fit lessons, unconventional hiring strategies, aggressive product development, and building content as a long-term competitive moat.

You’ll learn:

• How ClickUp attacked a crowded SaaS market dominated by incumbents
• The scrappy growth tactics that generated early enterprise deals
• Startup scaling lessons from hiring, product launches, and GTM mistakes
• Why modern B2B marketing strategy must include a dedicated content creator
• How AI SaaS features (including ClickUp 4.0 and Super Agents) are reshaping productivity software
• The balance between shipping fast and shipping polished in high-growth startups

This conversation dives deep into SaaS startup scaling, founder-led growth, B2B content marketing, AI integration in SaaS products, and how to build a durable brand in a competitive industry.

If you’re a SaaS founder, B2B marketer, product leader, or growth operator trying to win in a crowded market, this episode is packed with practical lessons.

Subscribe for more founder-led conversations on SaaS growth, AI in marketing, startup strategy, and building scalable marketing systems.


Entering A Crowded Market

SPEAKER_02

Even though click-up's a large size, we still move as if we're a very small startup.

SPEAKER_03

Like we're still very aggressive, we're still very hungry, we still spend like we're broke, negotiate like we're broke. The crowded space is always frightening, right? I'm assuming there were project management tools in the market back then. How do you attack a crowded space?

SPEAKER_02

One, look, you gotta be a little bit crazy. I mean, everyone told us not to do this. We saw the mistakes they had and we really believed differently. We thought there was room to come into space because with a crowded space does mean there's a lot of money there, right? You know, we lived together in a house. So like we had 5 a.m. standouts Monday through Friday, 7 a.m. Saturday and Sunday.

SPEAKER_00

We worked seven days a week. At what point did social media, organic social specifically, become like important to Clipka? Yeah, the first thing for me is is just hey Chris, thank you so much for being with us here today. We're super excited to be telling out a chat with you. We've been power users to an extent of ClickUp. I definitely would say the support team and the marketing team, we we couldn't live without ClickUp. So it's exciting to have you here.

SPEAKER_02

Yeah, I mean, we're power users for you as well. And yeah, I remember the first days starting ClickUp. I used to wear like our swag and our sweatpants, just waiting for someone to like, oh, I use ClickUp. And that took maybe a year and a half, but then eventually I was in the airport and I sat on the plane with someone who's like, Hey, I'm a customer. I was like, Yes, finally, we are getting somewhere. Let's get on some t-shirts before we yeah.

SPEAKER_03

I think we started noticing that last year as well, right? The conference where people would like come in and like, oh, you know, we're using you as well. That's what it's a really good feeling. The best feeling. That's a good feeling.

SPEAKER_00

Yeah, man, like ClickUp has has blown up. I mean, it's it's hard to talk to anybody who runs a business or somewhat related to someone who runs a business that hasn't heard or uses ClickUp. I'd love to hear a little bit more about how it was in the beginning and like the journey of the city.

Founding Story And Early Hustle

SPEAKER_02

Yeah, so it wasn't always so easy. You know, at the beginning, it was just there was four of us uh founding on the founding team, and then really we had like really three or four others who were there. One was like a contract at the beginning, and funny enough, you I'm speaking about this because we just got back from an OG off-site where we took the original seven to the Dominican Republic and we celebrate how far we've come, still did some work together and you know, planned for the future. But the way it started was we were in Palo Alto, we were living in a house together, and it was really just going relentless. It was a pivot. We had originally started a social media app that was a competitor of Snapchat because back then they had these fatal flaws, right? Snapchat erased your best memories in seven seconds. So we created an app called memory. And I really thought that was gonna be our calling. We're gonna make the next Zuckerberg, and we were doing well until Snapchat came out of Snapchat Memories and just completely ripped off the idea we had built. And it was a good lesson for us. But we pivoted, and that's how it started. We were living in a house together, and we didn't really know what to do after we basically lost a lot of our investment in trying to build that competitor. But we had built this tool that we called Mission Control Center, and what that was for us was just a project management tool that so we didn't have to switch. We were tired of like some people using Trello, some using Asana, some using Jira. So we built this for us and we decided to go to market with it. And so, you know, it took some time to build. We studied the market. We were in a house. I was our first sales rapper, first marketer. Uh, and the rest of the team was basically just dev in operation. So they were building the tool. And what we did was we built this tool called AppGator. And what App Gator would do is it would take all the bad reviews from all of our competitors. So anytime someone reviewed a two-star of Asana or a one-star of Trello, we would get that notification. And one, it would help us learn what to build and what to fix, what was wrong with the space that people were mad about. And then two, I can hit them up and be like, hey, let me give you click-up free. We're trying to, we hate Asana too. We're trying to fix that problem. And so that was like a GTM motion, but also a product motion. So early on, we were just building everything we could to try to stand out, anything we could that would fix the problems that we saw. And the problems that we saw were that most people were trying to make you work a certain way. They weren't being very flexible. And since we were new to the space, we came in at a great time, at a time where people weren't shipping fast, they weren't creating new features, they were making you work a certain way, and we did none of that. We were completely customizable, fully flexible, and I think that's what kind of got us going.

SPEAKER_03

So a lot of times, and we talk about that a lot, is that the crowded space is always frightening, right? So there is, I'm assuming there were project management tools in the market back then. Amazing tools. Amazing tools, right? And normally one would think that such a crowded space with amazing tools would not naturally be the kind of idea one would have. Absolutely. Right. So yet you still did it and still a lot of success. What is the contributor? Maybe the pattern to follow, like how do you attack a crowded space? One, look, you've got to be a little bit crazy.

Pivot From Social App To ClickUp

Scrappy GTM And AppGator

SPEAKER_02

I mean, everyone told us not to do this. You know, Dustin from Asana came from Facebook. How are you gonna compete? They have so much money. I remember so many of those conversations. But we saw the fatal flaws, like we saw the mistakes they had, and we really believed differently. We thought there was room to come into space because with a crowded space does mean there's a lot of money there, right? The recipe that I would say is is number one is being scrappy, right? I know that sounds very generic, but let me break it down. Two things we did that really changed everything for us and that called being scrappy. One is the first I told you building that tool, that's scrappy, right? Like that's getting us direct leads. That led to a lot of big deals, but that's something other people weren't doing. I'll give you a second example. We were always, always obsessing over the competition, learning everything we could about the space. So we were in every Facebook group. We were everywhere. And so I saw when I was in this Facebook group that one of our competitors was shutting down, they were closing their doors, and they were not building an export. So imagine if I came to you guys and said, hey, your ClickUp two weeks, it's done, and you lose all your work. You lose everything you have. We're not building an export. You're freaking out, right? That's all your work, work you've worked on for years. So we went to our CTO, Alex Rkowski, and we're like, hey, could you build an export in time to export all their stuff into ClickUp? He's like, I think I can. Stays up, you know, day and night, ordering Chinese takeout, chugging coffee. He builds it with like three or four days to spare. So I pop into that, you know, not a bad size project management tool. It's called Productive. Pop into their Facebook group, say, hey everyone, I know you've been terrified about losing your work. Follow these steps right here, and you can export it right into ClickUp. We'll take care of you. We're happy to have you. And all of a sudden, we onboarded all of their customers. We had way more, I had to go hire like six customer service reps and some account managers because we there's an influx in customers at that time. So the first thing I would say is being scrappy, like going out there and finding extra ways, doing things people won't do, staying up late, pitching ideas while you're at lunch with your team, at dinner with your team. You know, we live together in a house. So like we had 5 a.m. stand-ups Monday through Friday, 7 a.m. Saturday and Sunday. We work seven days a week. So of course, when you're putting that many hours in, you're together, you're pushing, certain things are gonna come together, certain ideas are gonna come, and then you have to really execute those. Secondly, you know this, but I'll give you the deeper part of the recipe is is hiring. You really got to hire right early on. But now, what I challenge you to realize is that you don't just go hire, like as soon as we got funding, we went and hired like CTOs of these major companies. You know, like I don't think you necessarily need to do that. I wouldn't even say they're necessarily better. They've gotten a little bit comfortable, right? They don't move as fast as you. I think you just got to go out there and find people who have a chip on their shoulder. People who are unconventional, right? Like hustlers, someone who's been through something hard because they can come in and they can give you their all and they can learn from you. How do you spot that though? I'll tell you how we did it. There's a couple ways. In the early days, what we did is we asked one question in every interview, and it was, what's the hardest thing you've ever done? And you want to hear it. And if they have to do some easy answer, probably not gonna work out. That life's been too easy for them. But you have someone who's really accomplished something or really been through something very tough, and they came out strong and they have a positive attitude about it, they're probably gonna be pretty good because it's tough working at a startup. You know this, like it's it's hard in the early days. We don't have much money, very intense. You don't know if you can make payroll the next month, right? Like those days are tough. Not everyone can they don't need to know. Yeah, they don't need to know, but you know it's done for you. It's not me enough done for us. But sometimes it's good to put the pressure on them. The second thing we do is we just have them start coming and work with us. We'd have them come work with us because like anyone, you can give them a test and anyone can go like hire someone else to do the test for them. We'd bring them in and just say, okay, you're gonna come sit in the office and you're gonna work with us for a couple days. We'll pay you for it. And they do that. And that's when we felt like they could be a good fit. We could see them in there, we could see how they worked, see how they, if they just asked everything, if they went and tried some initiative, went through things on their own, docs, stuff like that. That was how we did that in the early days. And now, still the same. We still kind of have to bring them in and because interviews don't always cut it. Anyone can say the right thing, but can they do the right work? Can they think the right way? Can they move on their own? Do they need a lot of help and hand holding, or do they just dive in?

SPEAKER_03

Interesting, you talk about the office. You think you could have done it without a physical office? Yeah, yeah, there's a lot of companies, like including us, for example, we do not all remote for a variety of reasons. Sure.

SPEAKER_02

I say it that way, but not everyone was in the office. Some we just we do through Zoom and maybe work beside each other. And but a lot of times at the time we were in the office. So I just I'm referring back to the really early days because and as we were in San Francisco at the time, uh, and that was that was how we did it. But definitely we still do it now, and we we had them come in on like long meetings or work sessions, and we just see how they contribute.

SPEAKER_03

That's awesome. Yeah, because we've been talking about whether the remote uh work fosters the the necessary degree of sort of the startup intensity uh versus if you are in the office and you are able to kind of uh you know be in each other's sort of spaces and collaborate. And we kind of have to be remote for a variety of reasons. Again, the cost of resources, the availability, even, because we compete with the likes of ClickUps, you know, to hire people, you know. And you guys compete with the likes of Meta, you know, you know, there's always you know, so AI, so and and we are very geographically dispersed, so we've always kind of thought whether that was you know helpful or detrimental element to this all, but it sounds like you guys have been had success in both. Both.

Winning Customers During Competitor Shutdown

SPEAKER_02

Look, and to this day, we have an office in San Diego, we're remote as well. I'd say we're kind of in the middle, but I one thing I will push back and say is we do believe that magic happens in person. And what I mean by that is again, we're gonna hire anyone where they are. We want the top talent no matter where they are. Top talent will get work done, they'll do just fine at their home. But what we do is once a quarter, maybe twice a year, we fly out a lot of teams and we bring them to our office together. We put them in a hotel, we've worked at a good rate with them. And for the whole week, they're gonna stay and they're gonna work together, and they're gonna have some big projects they're gonna work on. And we're gonna still like they're gonna work during the day, we're gonna take them out to nice dinners at night, we're gonna take them to a Padres game, we're gonna take them to a comedy show, you know, cool things like that. But there's some ideas, there's some magic that happens in person that we still believe in. So we still try to get as much in-office work together as we can, but we don't cut anyone off or not hire them if they're not near the office. Like I live here in our offices in San Diego.

SPEAKER_03

Any like maybe mistakes that you guys have made that maybe take back the time you would have done differently? I mean, granted, a lot of success, but sure, sure. No, we made tons. Lots.

SPEAKER_02

I I think hiring was a big one for us. I think early on we got some funding. We just hired, you know, the top names from the top companies, and honestly, they didn't work out a lot of them. I'm not saying all, but but a lot didn't. And I think we had more luck either acquiring and aqua hiring or uh finding people from smaller companies that were ready, still ready to grind. Because even though clickup's a large size, we still move as if we're very small startup. Like we're still very aggressive, we're still very hungry, we still spend like we're broke, negotiate like we're broke, we still do all that. Like people hate negotiating with us. We got we got this guy named Jason Wooten, who uh I used to work with at C Ven, who we brought in. You don't want to negotiate with him. Uh well maybe you'll see it in about a month. Maybe luckily your prices are pretty fair, but if not, he'll be he'll be coming in.

unknown

Oh no.

SPEAKER_02

No, I think it's for a lot of the, you know, for but he comes in and negotiates almost every deal we have. Uh I would say other mistakes we made were moving off, you know, because we got bigger moving off things that still work for us. Like I think we at some point we got away from doing, you know, discounts and and cool things like that, because that's what they tell you to do as you get big. But we still notice that that's a good way to bring on new customers. So obviously you gotta be smart and you can't go on App Sumo and give your product away for ten dollars, like we definitely did in the early days, like a lot of people did in the early days, right? We did too. Everyone did it, right? But it's a good way, but then you pay for it later. So I think there's there's a way to there's a way to do it. Um let me think of some other mistakes we made.

SPEAKER_03

I think, oh man, I mean, so many. Like bad features, maybe, uh like maybe something on the product side where you built something that wasn't necessary. We've done is we're very aggressive. We've built almost everything, right?

Hiring For Grit Over Big Names

SPEAKER_02

We have whiteboards, we have docs, we have almost everything. But I think you realize at some point that you can only put so many resources so many places, right? So you might we might rush to release docs just to get it out, but then it might be another year before we get it to where it's like competitive in the space, right? As good as everyone else. So there's one, I think one thing we could have done better is is maybe not rushing to like not releasing the tool until it's really ready to go. That's just something because we're we're aggressive when it put things out. And another one, we really messed up our 3.0 launch. We said a date it was gonna come out, and I think it took us like seven, eight months after that, right? So that's that's a big mistake. So on 4.0 that we just launched last week, we didn't say a word, just came out. We definitely learned from our lessons on being too aggressive on the product roadmap. We're we're still aggressive internally, but we will not announce them until we feel a little more confident because you just never know.

SPEAKER_00

It was a pleasant surprise logging in and seeing that animation 4.0. I was like, whoa, I gotta check out what's over here. You know, that was so cool stuff.

SPEAKER_02

It's a fun way to do it rather than hype it up and then be late, and everyone's like, where's it at? Where's 4.0?

SPEAKER_03

Where's 3.0? No, we are in the same mentality of releasing perhaps a bit too early because we are in that sort of excitement and that press to kind of surprise, you know, to get this in front of the user. And obviously, support team gives us a lot of slack for it, you know, because because that does come at that kind of expense of maybe stability issues here and there, a few extra complaints from the customers. Is that kind of the reason the rushing was a bad idea? Or is this like more about like giving less completed?

SPEAKER_02

Let me make sure I clarify. I still think the rushing overall is a good idea, and the reason why I do is because I think so many companies over fixate on like, oh, if we release this with a bug, you know, they're gonna be angry. They're really not as long as you correct them fast. So what we would do is we'd chip fast. And we didn't really have a bug team back then. So we'd ship fast, and we still ship fast today. But if someone had a bug, we'd make it like a good thing. We'd say, like, thanks for reporting that bug. That's it. Here's two months free of clickup. Well, and I'll I'll let you know the second it's fixed, and we'd hot fix it to the top, get it done, and I'd say, hey, here's your two months free of clickup, thanks for letting me know. So people get excited, they almost became like our bug team. Like, oh, I can free click-up longer. So we start hooking them up, and then people did a lot of them. We end up hiring some who were really good too, like really kept spotting and finding good bugs. Yeah. I just meant that like for some larger things that we've released, like a big feature. I think maybe in the future we can wait a little longer and make sure it's a little more polished for putting it out.

SPEAKER_03

Yeah, it sounds like you guys are taking just as much sort of reasonable risks. Uh, you know, would uh did I hear you right? No QA team? That's that was back in the day. We definitely have to be able to do that. Back in the day, too. No, he is giving we getting that. So because I'm for the same reason, because QA team, as good as it's is in principle, it's gonna slow us down.

SPEAKER_02

It does slow you down.

SPEAKER_03

That's I mean, so we've been developing like processes on top of processing, including involving certain customers that are providing enough beta testing, improving processes internally. But yeah, it's it's quite unorthodox, quite extreme. I think it's a small enough to do it still, but we need it now for certain things.

SPEAKER_02

But I wouldn't say our QA team is massive by any means. I think we're trying to do something with AI as well, as much as we can.

SPEAKER_00

I wanted to ask too, because a lot of our audience members are either brands, markers who are in the social space that they might be thinking either, hey, we're we need to start working on a broader strategy for social. At what point did social media, organic social specifically, become like important to click up? Is it somewhere along the way, was it early on where you guys realized we gotta be on there, or do you think later on, as you implement other strategies, it made more sense to start being more active on social?

SPEAKER_02

So in the original team, we actually used to work on a social media agency together in the early days. So to us it's always been important. We've always known the power of good social media. But when it really became something that we focused on is it's kind of when you know I moved off of doing sales and really started focusing full-time on content. And that's when I went to the board because I basically have been really good at making bets. And I do this by watching B2C. When something happens in B2C, it's probably gonna work later in B2B, right? Like I was doing influencer marketing like five, six years ago. Most people just started within the last three years in B2B. They weren't doing it as much, right? I really went heavy on it early and I saw a lot of success. And then now the bet that I made like a couple years ago was that every company would have one creator, one creator who creates content for them consistently. And, you know, now I think it's even going a step further. I think everyone's gonna have their own like mini TV shows, and that's what I have now. I mean, basically I'm running an operation that feels like TV. I've got actors, I've got writers, you know, we've got writers' rooms. We shoot for 10 hours a day, once a week. You know, it's a it's a very serious operation. I think if you want to win in today's world of content, you gotta take it serious. And that's why, you know, that's why I do love using Vista because there's a lot of pages I got to keep up with. I don't just have ClickUp. I got ClickUp Comedy, ClickUp Man on the Street, I got ClickUp Memes. You know, I got a lot of different pages. And I even have other shows that I'm starting on the side. So at the same time, I like I like being able to manage it in one place and see everything's going on. So shout out you guys for that. You do make it very easy to see my stats and to make sure I know how well we're doing. Uh that's been well schedule everything out. It's been super smooth. Any company not taking content seriously is in more trouble now than ever, because with AI, almost anyone can build anything, right? So you need some type of moat. You need some reason that people think of you and you need eyeballs. And if you're not getting that, you're probably gonna have a tough time.

Office, Remote, And In-Person Magic

SPEAKER_00

A ton of our audience and our customers who use ClickUp too. So with the 4.0, can you give us some highlights of like this the most exciting things, maybe through two or three things that you're super excited about?

SPEAKER_02

Yeah, the first thing for me is is just the hub on the left side, your personalized hub, right? You can have everything right there as you log in. So, you know, most of the time when you wake up, you go to work, you gotta have your email here, another tab for your docs, another tab for your calendar, another tab for your goals. You don't have to do that with ClickUp. It's all there in your in your home page, right? So I think that's the most beautiful part that people are loving the most, is just this personalized hub that you design, that you make it work your way, and you set everything up. Second thing is having chat right there as well. Everything kind of starts with chat. But the problem is most people use Slack. So they're in Slack and they talk about something, then they're gonna go back into their Google Doc or whatever else they're using. With us is different. I can be chatting and tell you, hey, hey, Reggie, let's go ahead and get this done. Right from there, you can create a task inside the chat and you can link it. Or with inside the project, you can have the chat, then you can have your list of tasks. It's all right there. So nothing gets confused. I think that's a really big plus. And the last one is the two letters that no one's ever heard is AI. I think we have a great job of implementing AI inside of 4.0 and the fact that you can talk to AI anywhere inside of it. So at any time, you can say, what have we gotten done in this specific project of the last six hours? Or hey, there's a lot of tasks that have been logged. Give me a summary. What did everyone get done the past three days? Or hey, here's this doc. What's the important things I need to know for my job? What's important for Reggie? You know, like what's important for me, and then go and take that back. So I think that's some of the really cool 4.0 features that I'm loving. And I almost forget because I've been using it for some time.

SPEAKER_00

That's amazing. I mean, Vitana were talking about how a lot of companies right now are overhyping AI. They're implementing things that people don't want. They don't care, right? Like, but I love seeing companies like ClickUp where we're looking at the workflow of what are our users doing? What are the things that we can do to either speed things up, to give them better access to data, to like superpower them, right? And kind of in an agent or whatever it needs to be. So it's awesome seeing you guys work on that stuff.

SPEAKER_02

Yeah, and that hyped me up for the next thing. We do we do have super agents coming out as well. The beauty of super agents with ClickUp is like you said, most people have AI, they're being forced to use it, right? They got these crazy workflows that take so long to set up. So we wanted to fix that because we want agents to be simple. Like you shouldn't have to really build out the agent, make it complex. And with ClickUp, you can build it, but it's very simple. It's plug and play. Like I want this to do this when this happens, and you can set it all up. And we're connected to all the major models, right? So if you want to use Claude for part of it, you want to use GPT, you can. And again, you can just pay for ClickUp and you get all of them in there. So that's that's a great little plus. But the other part is that there's a lot of monotonous work you shouldn't be doing. And you shouldn't have to keep switching and dragging your files in. You just tag one agent. Create the agent, tag it, let it do its work. Wow. Awesome.

SPEAKER_03

Yeah, we've been we've been also working on quite a bit of AI, and uh some of it is very much accurated in that same.

SPEAKER_02

What's some AI stuff coming with this now? I'm excited to see it too.

Mistakes: Hiring, Discounts, And Roadmaps

SPEAKER_03

Uh, we have the AI summarizations within the inbox, uh, sort of to help you respond. That's what you know the users are interested in being able to respond to. That's a good one for us. Like, hey, what's the main messaging in this inbox? Well, the to summarize the entire conversation, identify opportunities, you know, with that user, generate the response. It does it in your brand voice, you know, whatever you know, you've come to define. We've done AI summarizations of data, sort of spending you know, half an hour trying to figure out the key trends, got a summary there. You know, we are expanding AI and content. We're looking at some content generation, like images and videos. So, yeah, it's it's an ever expanding.

SPEAKER_02

So you could you could create it inside of Vesta. So, hey, I need a uh design for 4.0 release.

SPEAKER_03

So, if we can overcome the you know the extra hand or extra head or whatever the side effects of all these image generators are it's a work in progress. But yeah, AI is super exciting space, and uh, we also like on the lookout for a lot of ways to automate.

SPEAKER_02

Yeah, I love that. Again, we have a pretty massive operation, right? And and I was glad I found Vista on my own two years ago. I've loved I've loved everything I've used in you guys, love the features. I just think you have the best cost. So you get the most value. Most of these others charge a lot more, and you guys offer all the same things. So I never understood why more people aren't using Vista. That's why I speak about it on stage and everything else. Yeah.

SPEAKER_00

Well, thank you so much, Chris. I appreciate your time. I know we're running out of time here on the studio there, but I appreciate you coming to the show. Yeah, absolutely. I'm excited to have the whole team dive in to click up 4.0 because I don't know that anybody else on the team realized. I'm the first one who saw the animation. I'm like, I'm I'm about to start creating a lot of things. Turn it, man.

SPEAKER_02

Turn on the workspace if you need any uh if you need support, let me know. I can obviously plug you in. Thanks, awesome. Yeah, thank you. Awesome.

SPEAKER_00

Appreciate it. Yeah, it