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The Playbook Behind ClickUp’s $4B Content Engine
Speaker
Blaine
Speaker
Chris Cunningham
00:00 Scaling ClickUp's Viral Content Strategy 04:14 "Content-Driven Sales Transformation" 07:21 ClickUp's Messaging Strategy With Creators 09:53 "Effective Marketing & Sales Strategy" 13:16 "Consistency in Content Creation" 19:29 Executing Creative Video Concepts 22:34 Starting a Brand from Scratch 24:42 "Formula for Going Viral" 28:29 Audience-Centric Content Creation Strategy 32:18 YouTube…
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“Free Private Community for Aspiring Content Creators: "The best news, this community is absolutely free to join, but there will be a vetting process to make sure that you're serious about your content and personal brand and you're ready to support others.”
“Exclusive Free Community for Serious Content Creators: "The best news, this community is absolutely free to join, but there will be a vetting process to make sure that you're serious about your content and personal brand and you're ready to support others.”
“I took a bet that I thought all companies were going to have content creators if they wanted to be, you know, to really compete in this game.”
“I took a bet that I thought all companies were going to have content creators if they wanted to be, you know, to really compete in this game. I thought they're going to have some kind of creator they hire that creates content for them consistently because they're better than just asking some of your employees at the office to create content, right? They're always going to be better. It's what they do.”
“I took a bet that I thought all companies were going to have content creators if they wanted to be, you know, to really compete in this game.”
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Today we're joined by Chris Cunningham, a founding member and head of social marketing at ClickUp, the AI powered productivity platform, which is valued at, I believe like $4 billion, maybe, maybe even more than that today. But Chris has been instrumental in shaping ClickUp's brand voice since 2017, transforming their social presence into one of the most influential B2B SaaS with over a billion impressions in 2024 alone, regularly generating 200 million plus impressions per month. So in today's workshop, we're going to cover how ClickUp's content started small and evolved into a viral content machine. Uh, we'll talk about key pivots and breakthroughs and moments that define ClickUp's content strategy and the lessons that Chris and the team have learned along the way. Um, we'll talk about building repeatable content systems and as well as a team culture to be able to keep things moving, keeping things engaging week after week. Um, and also ways to measure and monetize your content engine. Like, how does it work once you're creating content? How does it actually translate into, into business? Everything from a big bet like a Super bowl bowl ad, to more regular, everyday sort of content series. And lastly, we'll be just talking about advice in general for creators, marketing teams looking to scale up their content and turn it into business.
So with that, Chris, I'll let you kick us off. Why don't you give us a little bit about your background and maybe how you got involved with ClickUp from the early days.
Yeah, so I'm on. The original four started ClickUp. It's been a wild ride. Before that, it was the same crew we had. We, we started an agency, we did really well, in the early days in Charlotte, North Carolina, made some money, decided we wanted to take on something bigger. So from there, we built a social media app that was a competitor to Snapchat called Memory, because at the time, Snapchat would erase all your memories in seven seconds. So we thought we had this great play. We were doing really well.
We moved to California. We were living in a house together in Palo Alto, building this, and everything was going great. I thought we were gonna be the next Zuckerberg until Snapchat came out. With Snapchat Memories, we lost all our money, lost everything. But in the interim, we had built a tool because we didn't really like Asana, Trello, Jira. We thought it was weird that he had to log into so many different types. Like, developers would use Jira, you know, marketers would use Asana. Just didn't make sense to us.
So we had built our own internally and we decided to go to market with that. It's kind of our last hoorah until we had to go back to, like, work, you know, different jobs. There's our last, like, entrepreneur run, and we locked ourselves in a house, you know, then Palo Alto. Kept working, worked crazy hours, and we, you know, first. First year was tough. I was our first sales rep. First, like, customer service rep and really marketer. And so I was just kind of trying to be scrappy.
I remember closing our first deal and then starting to close more deals. But ClickUp's grown a lot since then. I think we've really kind of shown that customization is really important in software. And then now branding as well. So I've shifted my focus. Who knows? Our first sales rep. I'm obsessed with marketing. I love content and I love creating leads that way.
And so I think now I can build more leads for ClickUp by creating content rather than just, you know, closing deals on the phones. So, yeah, my role now is head of social marketing. I get pretty big goals every few quarters. The first one was 100 million impressions in a month. I hit it, then I hit 200 million, and now they've asked me to find a way to hit 300 million. So I do that by creating what I would call different shows. I have many different pages because obviously it's hard to get one page to hit that many. I focus on different platforms.
I talk to experts from all different types of platforms. I'm trying to be omnipresent, be a little bit everywhere. But, yeah, that's. That's my mission now.
So I love that. I love taking the approach of like what you just mentioned, having that lens and starting in sales and then seeing, wait a minute, content is a valuable way to, you know, not only get your name out there, but generate real leads that can turn into business in a super, super meaningful way. So rather than just saying, oh, I'm going to build a sales team and go outbound, outbound, outbound, you've really flip that on its head and now you're able to generate tons of impressions which lead to inbound and growth of the company. So why don't you take, take us back to initially just getting your content set up because at a certain point in time, click up and your content game was just like everyone else, right? Like, you know, you guys hadn't, you didn't have a ton of traction. You weren't doing 100, 200 or 300 million impressions. So what did it look like in the early days? What were some of those first, you know, what were some of the first shots on goal that you guys were taking and. And what did it look like? And really building out your content? Motion.
Yeah, I love you use that term. We're very big on shots on goal. We want to put as many shots up as possible, but we want to have calculated shots. We want to take them with low budgets, right? Because the, the way we work at ClickUp, even though sure, we've raised some money, but we're not just going to throw money away. So we're very, very. We take. We take bets is what we call it. So I'll make a bet and I'll start it very cheaply.
So at the beginning of early days, it was just me making videos, making, I tried raps. I've done a little bit of everything just trying to make content. And then I realized that the only way is really going to scale is about brought in like an expert. And it's a bet that I took like what, almost a year and a half ago now. I took a bet that I thought all companies were going to have content creators if they wanted to be, you know, to really compete in this game. I thought they're going to have some kind of creator they hire that creates content for them consistently because they're better than just asking some of your employees at the office to create content, right? They're always going to be better. It's what they do. So that's what I did.
I found. I was like, give me a little budget to get one creator. And there's one who I had my eye on for a while. His name is Luke. If you've ever seen our content, he's the guy in the blue shirt, very funny. And he was creating content for a company called Ad World. And I knew he was good. He had grew that page in such a massive way.
And I just kept telling him, hey, they ever let you go or anything like that, please let me know. And they did. One day out of nowhere and he has a family and he's like, I don't know what I'm going to do. And so I sent him a check the next day and hired him on contract. But I wanted, I was like, let's just prove to my COO and to the board that we can hit some numbers because I know they'll give me more budget. They always do, as long as I prove something and show something. So the first month or so, you know, we had some hits, but nothing crazy. It took us probably like that six to eight week mark before we really started having some videos hit.
1 million and 3 million. And I think we hit like a 25 million month. And that's when they were like, okay, this is awesome. Let's, let's ramp it up. So we hired him full time and then he was like, hey, look, I, I really, I feel like I need some help. You know, I'd like to have other people in, in this. And that's where he scaled it up again and, you know, hired another actor, Adam, who's in the black shirt and they're now kind of termed the HR guys. But they're creating content for us every single day.
Every day. They're creating every day. We're iterating and, and that's kind of how it has to be if you really want a chance to, to compete in this, in this game, in my opinion, on a high level. So, yeah, we have, we have two full time actors that are acting all the time. They're building scripts, they're doing commercials for us, a little bit of everything there.
And Chris, tell me a little bit about, you know, what the product is that you were trying, like what were you trying to communicate is the message? Because like you just said, we're talking about all these different form factors. We're talking about scripts and videos and like, you know, we can be funny, we can do skits, all this different stuff. But at the end of the day, you know, one part of it is entertainment and getting those views, but another part of it is, know, building that brand recognition so people know who you are, what your product does, all that sort of stuff. So, you know, Going back to that, when you're bringing on that first creator, like what's the, you know, content brief that we're talking? Like what, what, what are the goals outside of just views? Like what, what are you, you guys as ClickUp trying to communicate and how does that, you know, happen through the creators that you're working with?
It's different for every platform. So obviously on LinkedIn I will still post some of the funny videos, but on LinkedIn I'm creating more thought leadership content. So at the end of the day I, I, I'm doing a mix of content. I'm doing top of funnel because I just want a lot of people to know about ClickUp. We believe in the product, we believe we can compete. So we want to get in that, in that, in that room, get on those calls that we are, you know, when people are shopping for project management. So that's where the top of funnel, the funny and, and things like that. So when you see our TikToks, our Instagram, you know, some people be like, oh, what is that? Does that bring leads? It definitely does.
You know, GaryVee was one of our bigger Vayner Vaynermedias one of the biggest deals we closed last year and they found us from, from social, right, that we had great social and then check this out. So I mean that alone more would, you know, more would pay for everything. But we've had so many leads that come in, we've tried to find a way to turn this into bottom of funnel as well. So with the HR guys, the funny content, that's just to get attention, right? But we'll find you later, we can retarget you, right? So now my CAC payback is lower because I'm running an ad with two characters you've already seen, you're much more likely to watch. And in that we'll make it so a funny video. But we'll go back to the product. So I don't just have them making the funny video. Sometimes I'll mix in products and they'll make the funny video.
Then I'll go to our, our mograph team and they'll find a cool way to bring in the product and we'll make it to where it's not still, not too much. We still enjoy the video. So that's kind of our play there. LinkedIn. I'm creating more thought leadership content, visual carousels, things like that. Same with X, you know, X X is probably our weakest platform. I'm still trying to, to figure that one out. As a brand account.
And I think we really need to create content through our CEO on that. But the other thing we're doing is we're creating thought leadership content. So I'm creating content. Gwar of our CEO is creating content. Zeb or CEOs creating content. Because a lot of people like to learn from real people now too. So especially on LinkedIn and X, that's what, where that wins the most. So that's kind of our play on that.
But then the day we want signups, we want attention, it's a little bit of everything. At the end of the day, if this is a machine for what it cost us, this is a machine that just gets us attention. It's well worth the money spent. But we love tracking and putting QR codes on there and showing that it does close leads as well, which it does. And then the last thing I'll say is there's many, many times when a sales guy or sales rep will hit me and say, hey, this deal's about to close. They keep mentioning how they love the HR guys. And so what I'll do is I'll, I'll have them on their next shoot make a personalized video for them. Something easy, something low effort, but it shows we took the time to research who they are or if there's a champion on a deal that's close to closing, the deal is already closed, anything like that.
We'll send them like personalized videos. And one more thing we do is we also have an AI tool that allows us to see who follows us. So I know that the CEO of McDonald's follows ClickUp comedy. Of course I'm going to make him a custom video and send that. And it's much more likely to get a book, a demo than just random cold email.
One thing that you said there that was really cool was about how content is one part of like the entire funnel. So when you guys are thinking about it, it's not just entertainment for the sake of it, it's you're building awareness. You've got an entire content, an entire growth motion set up to either, you know, retarget them, bring them through the funnel. So I think when you're thinking about it, you know, I, I think that's a, a very important perspective to take on content because it's not just about how content does by itself. It's like, how does it fit within that whole growth ecosystem. The other thing that you mentioned, the, the other thing that you mentioned that, that I think is like really important is like you're like, our CEO is creating content. I'm creating content. Our team's creating content.
What does that look like in your day to day? Right? A lot of people get caught up in work, in all the other things they need to be doing, and they kind of, content kind of takes the sidelines. So how do you make sure that, you know, a. What's the content that you guys are creating? Are you working with teammates to script it? Are you kind of saying, hey, take care of this on your own? Are you blocking out time? What is that, that content motion look like for getting you and your team itself to actually be creating that content?
To me, content's just another task, right? Like anyone can make excuses. So if you're just not making content means you don't prioritize it. We, we prioritize it, but it's just time. You know, with ClickUp, we, we allow ourselves to, to. To schedule everything. You know, we, we have a lot of tools that allow us to go through and say, okay, at this moment, you know what, we have like an auto tool. So I'll say, okay, these are the 16 tasks I want to get done this week and it'll schedule it for me. I want it on my calendar because I'm taking a call.
I'm not moving on a task, right? Unless I'm not fully presenting the call. So it's on my calendar. I know that, you know, a good time for me to shoot is around like 6:30pm or 6 when the lighting's going down. So I'll do it once a week. Once a week I shoot four or five videos and then I have an editor who edits it. It's not that crazy. And then I'll use Claude or something. I'll drop it into Claude and then I'll have, you know, LinkedIn written post X posts about if I want.
I don't really overcomplicate it. I've already built the system out for me. You know, I already have the style guy that I need to give Claude to talk like me. And then I'll kind of put it out there. I'll still change it and make it my own, but I definitely use AI to repurpose and maximize every little piece of thing I do. Sometimes I'll just take a walk. I'll go take a walk or I'll go shoot basketball. And while I'm doing that, I'll have my headphones in.
I'll talk, I'll take voice notes and I'll put those voice notes, put them back in AI and then it gives me, gives me posts there. So I try to do as low effort as I can, but still maximizing it out and then having editors take care of the rest.
No, I think that's so important. Like, you're saying you block out time, even if it's once a week and you're getting a couple videos done. And I think that's, it's really easy to kind of fall off the, the pace a little bit and maybe, you know, say, I'll get to it next week, I'll do it next week. But like you said, just block out time and, you know, it's something that compounds and it's something that you need to do over time to be consistent. And you can't just, oh, I'm just going to create one video and then you don't do it again. Right.
100, I think. And it's easy to do. Like, I get it, but the, the dividends that you said that, that content rewards with is nuts. The amount of people I've met, the, the people who DM me and just what I'm learning, because I'm getting better at it every time. I'm getting better at speaking, I'm getting better at having, you know, a voice and, and a take on things, so there's no reason not to make content. And I, again, if I'm going to keep pushing it and talking about so much, I got to walk the walk as well, 100%.
And I'd love, right now we've got a bunch of people in the audience who are watching. I'd love if you could maybe even share your screen and you could just kind of show us so people get an idea of, you know, your content, the content that you're overseeing, the types of different assets that your team's working on. Is that something you'd be able to do, like, pull up, like, maybe the Instagram or something like that?
You mean look like, show. Show our Instagram page? I can do it.
Yeah. Yeah. And just kind of. So that way we can kind of.
The two we create content for the Most are like LinkedIn and Instagram. I would say like TikTok. So I'll show both.
Sweet. And for everyone who's listening live right now, if you want to just drop any questions that you have, we're going to open this up in, you know, 15, 20 minutes or so for, for live Q and A and stuff like that. So as Chris is going through this as he's showing content, if you have questions about your Own workflow. Go ahead and drop those in the comments and we'll be able to. To get those. Get to those right after we wrap those.
I'm sharing, Blaine, but I think I need you to click.
Oh, I believe. Do I? Let me see where I see this.
When I click it, it doesn't pull it up.
Oh, there we go.
Maybe Lorraine.
There it is.
Can you all see it?
Yeah, we got it.
Sweet. So I'll give you like a rundown of what we do. Instagram is very video heavy. Right. I'm trying to win. So what I do is called the ABCD formula. And what that means is when we. You need to go test content for like 40 days before you do anything.
Just go test, like do 40 videos. After I do those 40 videos, what I'm doing is I'm going back and looking at them and rating them. If something does really well like this and gets 1.3 million likes, I don't even remember how many views I got. Yeah, 35 billion views. Something does that. I'm obviously going to redo it. Right. It did really well.
I'm going to make that again. And that's what we did with hr. Goes hard. And you'll see we do that probably once every two weeks. Because I learned if I do it too much, it exhausted. But here's another version of it. And it did great. Right? 10 over 10,000 likes was.
Because I have a repeatable formula. I know that when these two guys start dancing, they bring back nostalgic songs and, you know, and business jargon and things like that is going to do well. Another one we do is making fun of different. Making fun of different, like, positions. Right. So when the. At. When the IT guy does training, I don't know if you can.
Oh, yeah, we can. Really? So we can't hear it, but it's.
Oh, sorry.
But clearly it's like it's relatable content. It's content that's shareable and. And that sort of thing. Right.
Simple video. We have our main actor in there. Then we have, you know, a girl from the office. Like our girl is just at our office, just, you know, in there. So super lightweight, easy. I mean, now we got 154,000 likes. I think I got like 10 million views on total. So again, super relatable.
It's just. It's just showing it and everyone knows in it. It's like the five things they say all the time. Did you submit a ticket? Did you restart your computer? Right. That's all that is. And it did really well. We also still do some images and stuff. This one didn't do amazing on Instagram.
It did really well on LinkedIn. So we got like 4000 likes on LinkedIn. Dev versus dev versus dev. The one that did really well was PM versus PM versus PM. So I'm doing is. I'm just taking a thing where people get confused. Project managers, you know, developers. People know the different type of developers.
I'm just adding in, I'm speaking to the conversation. I'm helping people with work stuff. So testing on Instagram didn't do as well. All good. Because it did great on LinkedIn. We got pretty simple, right? Like this one did. This one did really well. We hop on trends.
So B. B is taking something like you've seen before and then putting in your own style. C is hopping on a trend. I recommend hopping on a trend like once a week. It's just quite simple, right. This probably took 12 minutes of just making things on HR. Just making these HR guys with the action figure trend. That was really popping off.
So you're always looking for trends and things like that. What's some other ones? We'll do music videos where you kind of replay like this is the next.
That's so fun.
We'll do music videos. We know those work. Then we'll do influencer videos as well. Because I'm still trying to show the product, the keys. I'm not sure the product every time. If I show the product every time, every time, I would not have this many followers. I probably have 90 or, you know, maybe 60k max. But we're going to hit 500k soon because we're making a lot of these other videos.
But we will, we will do great influencer class. Want to make it look cool.
Yeah.
We want to show what they can gain. So I, I highly recommend if you have a product or something like that, find good creators who you like their style. I would also jump on things that are happening in the world. So severance. Severance was a hot show. Whenever something like that happens, we're jumping on it. Right. I'm gonna make our own version of it in the corporate world when.
When Squid games came out. Same thing. We're doing it every single time. We're jumping on all that stuff. These do really, really well for us. Corporate jargon going too far. So it's kind of like our style. We've kind of built your ducks in a row, all your eggs in one basket.
Right.
Simple. But. And this is me over here.
For.
The stakeholders and we just raise stakes.
That's so funny.
So it's just funny. Just a play on words, all that good stuff. We've even done, man, on the street where we go and ask for their salary.
Yeah.
And this is a new page. So you can see we have click up on the street. It's a whole new page we're starting where we'll be going on, like doing on the street type content. So this is a pretty in depth look at our Instagram.
Yeah.
And what is a different type of content?
And Chris, I love that. And what does it take to pull this off? Right. Like, I, I know you've kind of said you guys approach this almost like having a writer's room, like you're doing a TV show or something like that. So from, from an execution point of view, what does it take to, to, to execute on this? Right. Because like, some videos we're seeing, you're working with creators. Some videos we're seeing, you're concepting and filming yourself. Other ones are simple things that you're putting a graphic together. But from an execution lens, what does it look like to pull off something like this?
Yeah, I mean, you got to be on, if I'm being honest. So you got to, you got to plan every day. So every Monday we have a writer's room. That's where we write. That's where we think of these ideas. Right. So in a writer's room, we'll probably have like nine ideas. And then we'll, we'll meet on Monday, we'll kind of pitch the ideas on Tuesday.
We pick the best ones and we punch them up. And then Thursdays they shoot. So Thursday they shoot all day from 8 to 5. So that's once a week we're shooting and that. And that's their job. And sometimes we'll bring some actors in. Like, that's an actress right there. That's an actress right there.
And sometimes we have people in the office. Like there's people in the FBI agents, they're just employees. So we'll try to get them to help out. That's the beauty of having an office. Yeah, I mean, I think it takes week by week knowing that we're going to create, you know, seven to nine pieces of content and have editors on the back end who are editing. So every single week we have content, we have a bunch stacked up, and then we test it. We kind of see what we think is going to do really well. And then we, we post.
And then if something does really well here, we'll probably post it on, you know, LinkedIn. And I'd say videos aren't hitting as much as they were, but they're still definitely hitting like this. We just post an hour ago. We'll see if it's a 25. It'll probably get to like 70, 80. Nothing crazy, but we definitely have videos that hit.
Yeah, and a lot of engage. And a lot of engagement too.
A lot of engagement. We'll do a lot of product stuff as well.
And I think, Chris, one of the other things that you said that was really important was about the, the mix of content, right? Like it's not all bottom of the funnel. You're not always selling just your business. You're creating, you're creating content for, you know, in your case, your icp. Like who's the person that could relate or could use ClickUp? I'm going to create content for them that they can relate to. Some of that, yeah, is going to be very bottom of funnel in terms of like, this is exactly how you use my product. But the rest of it is like, you know, you're creating entertainment, you're creating shareable things, you're creating relatable things and that's how you're able to build a whole kind of content strategy.
And a lot of relatable too. Like just business. Like this is. This is nothing that. This is something that everyone's seen in the office, right? Can we just add one more thing? Original plan, they stuck to it. And what happens when you just keep dependencies, blockers, adding revisions, you know, so we just add stuff like that in there. But you'll see like some of the videos that do hit more on Instagram. We'll hit more on LinkedIn.
Right? 2275 likes. That's big. That's good for LinkedIn. I'm always pleased with that. So we can kind of tell what videos we should post on LinkedIn because they've done well by testing it elsewhere. I try to LinkedIn, you can't just post a lot like you can on TikTok. So I try to keep it a little careful there and then we'll have other people we work with. This is just someone who loves, loves ClickUp.
You know, post force there did really well. He really showed the product in a good way. And I'll take these all day long. 30 comments all talking about the product.
That's awesome. So Chris, I'd love to now, now we've talked about, you know, like the operations, how you pull it off, the strategy. I'D love to pivot a little bit to, you know, how you'd approach this if you were a, you know, if you were starting from scratch, right? Imagine you don't have this team, you don't have ClickUp, you don't, you're not pulling in 300 million views and you've got a business and you're trying to get it off the ground. Right. You're one person, maybe you've got a couple vas. You're trying to grow your brand. Obviously it's different for every brand and there's going to be a lot of questions that, you know, you would need to know for that. But, you know, just walk me through what your approach would be if say you were starting a product like ClickUp and you were starting from zero, didn't have all the writers, didn't have the whole team we're executing, maybe just you and a couple others.
What would your game plan be?
If I had to start over and I'm at a new company we're building in public, we're doing that right? Because why not like, hey, we're starting here. We have X amount of money. This is what we're spending each week. I'm building in public and I'm not hiding anything. I'm not gatekeeping anything. I'm gatekeeping if we're going to lose all our money. I'm putting it all out there because people love to see it. They love to see the in and outs.
I'm putting hidden cameras in our where we work and I'm just letting that go. And I'm paying one low cost editor ted it all up and I'm posting almost every other day as much as we can. The good times, the hard times. No actors, anything like that. Just, just talking about what we're working on. So at the end of the day I would just ask for like 5, 10 minutes of all the early employees and just say, okay, look, five minutes. What did you do today? You know, and I'd find a cool clever way to, to chop it up. Actually one thing, we should still probably do that at Click, but we're just all set free now.
But that's exactly what I would do. I would, I would just start building it public. People love it, especially on LinkedIn and LinkedIn is a powerful place you can start. Then as I got some budget up and we close a few customers, I'll go get some creators, I'll go find a creator who I think has talent but doesn't have the followers yet, doesn't have the backing and I'll offer them a chance. Like, hey, look, you can, you can grow yourself on this page. I'll pay you. You know, maybe it's only X amount per month until you grow and hit certain numbers, but no one's paying you yet anyway, so you might as well make content and get some money from it. So let's, let's do it.
And then I'll get them and guide them and work with them, show them my formula of. Of. Because a lot of going viral is more just a formula. It's even, Even if I can't tell you exactly how many, you know, what numbers I hit each month, I can get pretty close. Because I, I know if we keep creating, if we keep iterating and we keep thinking strong enough and, and repost, if we test hard enough and then we double down on what's working well, we'll. We'll get numbers. So I think just like anything good in marketing, whether it be ads, whether it be, you know, blog posts, emails, you gotta test and you gotta learn and you gotta iterate. And it's the same here in this game.
So iteration is definitely a big part of content. And you just mentioned, you know, a formula to go viral or to grow. And a lot of that, like we said, is testing. But how do you think about, you know, going viral or creating content that really has outsized reach? Like you. Even the, the video you showed us that did 35 million views, which is like insane. That's like an insane number for, For a single video. So, like, what's the, what's the framework that you're thinking in when. Before you know, when you're in that writer's room, when you're brainstorming concepts and you're like, I think we can create something that pops off.
Like what. What goes into a concept that you think might. May have a chance to, to blow up?
We. We touch into. It's like, how. How human can you get? You know, I'm kind of the opposite. Everyone's like, oh, streamline all your content with AI. AI is writing nothing that we're doing. It's not doing any of that. Right? I'm not using AI.
Use AI when it's time for sure. But I'm not using AI to create. Like, it would never create those ideas. Now my. Might be able to give me some cool ideas once I have it. You know, like, maybe you can throw. If I'm like, I'm stuck on like, what's another song we could put in here? You know, I'm like a brainstorm with AI there. But I think the real strategy is like, how.
How human can we get and what can we check into? So there's a lot of boxes that that video checks, and that's just 35 million on Instagram, mind you. I got like, I think 40 on TikTok and in a ton on YouTube. It went viral in China's YouTube. It was. It was crazy. That was the most viral video I've ever experienced. And the reason why is it touched on so many different things. It.
It. You all know one of those people who take their job too seriously, right? And then you all know those people who want it to be, like, actors or whatever. And then so when they get a chance at their job to do it, they jump on it. And then all the nostalgia, right? There's. Those are songs that you haven't heard. The Backstreet Boys, you know, Britney Spears, Toxic. We brought back songs and we. But then we put it to a business relatable thing.
So we just hit so many different parts of your brain that that's. That's how we knew it was. I knew it was gonna be hit when it was in the writers room before we posted. I didn't know it was gonna be this big, but I knew it was a hit. I knew there was a hit when I just pictured them, you know, now that even those outfits are, like, famous, even. There's no. Had to be the outfits they wore the first day. When I picture them getting up there and like, you know, a crowd watching them and just, you know, performing like that, I.
I knew it was going to be pretty big and. And it's just something you just don't see on social media. But it's fun, it's light, it still has a little business to it, you know, like, they're changing the words around. Like, instead of, you know, at the end, it's like the door is that way, you know, like. Like just anybody. You're getting fired. It's just so funny on so many levels. I think that's why we're in the writers room.
We're looking for that. Does it hit? Is it relatable? What catch your attention at the beginning? Would it make you want to see it through to the end? You know, is there things that would keep people scrolled away? Is the pacing good? Those are a lot of things we're looking for. Uh, and sometimes it's also just a natural good idea, like just something that's. That's hilarious and relatable you know, like, that's why that the video went viral, because it got shared. People share that they think of someone like, oh, my God, I want them to see this. That's what you got to create. You have to create. Some people, like, wow, like, think of when you're scrolling, you need.
And you need to think of yourself. Like, think of when you're scrolling, like, what makes you want to share, right? It's usually something that makes you laugh so hard or makes you think of another person. So if you're creating content and you know someone knows that person and they're going to share it, then you're much more likely to go viral. Because shares are the number one forms that I care. I don't really care that much about likes. I care about shares. The shares are going. The rest is going to be there.
Well, and I think that's so important because, like, literally what you just said is, and I think a lot of people are probably guilty of this is they're thinking about their product and then they're going to create content to, like, try to, like, push out noise. And what you just said is you want to be thinking about who's going to be consuming this content. And, like, what about the content I'm creating is going to make people actually want to share it? Right? Like, how. How is this content engaging? And so if you can pair a concept with the foundational idea of, like, what, you know, how am I creating content for, like, my ideal audience? Who's gonna love this and want to share it with someone? Then that's kind of like the prerequisite for a solid content idea. And then all those other check boxes that you talked about pacing, is, you know, is there a strong hook? You know, is it edited well? Is it, is it resonant? All this other stuff, like, that will happen and that'll increase the. The chances of it going. But I think a lot of times people think about content and be like, oh, I need to get the viral music and I need to do this. And Instagram has this rule about how and when I need to post.
And like, sure, all of that's, you know, that's important. But, like, a lot of times people miss the main and most important thing is, like, you were saying, the concept. And like, is this something that's relatable and charitable?
Yeah. And another thing I should add in there is you need to know your icp. So if you're creating content, you don't know who you're creating for. You really just kind of Lost the whole goal right there. So you can start creating as much as you want. So, I mean, I do things like this. Like I interview people like once a week. And I'm just seeing, I'm just asking like, hey, like, I will make content for them afterwards, but I'm, I'm literally just asking like, okay, like, what content makes you laugh? What added value? What's something you learned in your job that helps? That's, that's how I know how to go back and make some of these posts like the more educational content.
But also I'm like, what makes you laugh? You know, what are you laughing about? Because luckily for me, ClickUp's ICP is pretty broad, right? Anyone on this call can use ClickUp and I want them to, but, you know, so if you're not thinking of your icp, if you're someone who's like, your ICP is it, then you should be doing just like those IT videos I did, because that's why it went viral in the IT community. It got shared in IT group chats or another IT to another IT person or someone who knows their IT person share that video. That's why I won. So you know who you're talking to first.
A hundred percent. Okay, this is a question that just came up that we get a lot that I'd love to see if you guys have context into. Do you schedule your posts or do you like, do you use a scheduling tool that will like integrate with a LinkedIn or an Instagram so it goes out, or do you, are you guys posting in platform natively and you know, do you see a, a difference in metrics when, when doing that sort of stuff?
Yeah, I mean, a lot of people fight me on this and I don't really care. I, I don't, I don't do, I don't schedule posts. I, I have someone who I want to manually do it each time. I, I, I've definitely seen a little difference in it. People will fight me to the death and say there's no evidence that it. And that's fine, you keep doing it your way. But, but for me, in my operation, I put too much into this and I really think that I like someone posting. I like it, and then once they post it, they're there.
I also believe in warming up the account, you know, going and liking a few posts, commenting before. So to me it's just, there is no need to, it doesn't, it doesn't save me time like that.
Yeah. And I'm in the same exact Boat based on what we've seen when it comes to content. You know, we post everything natively and aren't using scheduling or integrated tools. So like you said, you, you put a lot into that content. The least you can do is, is have, have a human post it.
Yeah, I just, I think it's not that hard to do and. Yeah, and maybe I'm wrong. Maybe have. They've changed it now, but I definitely saw numbers go down when I did it. So I'm still playing game.
Other question I had was, you know, platforms, we've covered some of those platforms. You know, we talked about TikTok, Instagram, LinkedIn. But tell me about YouTube. Is that, are you, are you guys going in on YouTube? Is it part of your strategy? Do you work with other creators there? Where do you guys stand on YouTube and, and how are you thinking about things moving forward?
Yeah, I think we're at like 80k on YouTube and right now we use it as a middle of funnel, just straight, you know, this is how you use ClickUp. We don't really make so many videos on there. We do some YouTube shorts and they don't. Our videos don't hit as much on YouTube shorts. But I do want to change that. So I am, I'm talking to some experts right now to see I can really start winning on YouTube as well. Because if I'm going to hit 300 million, I need that, that channel to win as well. So I, I wouldn't say I'm like a super expert at it yet, but I'll probably just.
Do you know what I think is the smartest thing you can do? And I'll get someone who is good at it and get them to either contract to help us build or I'll find a creator and build there too.
A hundred percent. And that's the thing. It's like when you're creating a content strategy, it's like you don't have to win on every single platform a hundred percent of the time. You need to find the platforms that work for you and what you're doing. And then once you've cracked those platforms and you've got the process in place, then you can start adding in the next platform and building because everyone, every platform slightly different. There's different workflows, different things resonate with the audience. So that's something that like, you know, we've seen a lot as well. It's like find the platforms that work for you.
A lot of times in the B2B world, like LinkedIn's A Great Place to start and you know, or an Instagram or TikTok start there. Then you can layer in X YouTube and everything as you start to see success in those different platforms. So that, that's awesome.
Focus on one or two to start. I see Jordan asked a good question too. I don't do it. I don't do it either. And I don't know, maybe like, and talk about engagement trading. I know people do it and I know it definitely helps them and I'm not gonna sit here and lie to you and tell you I've never tried it. Definitely I've, I've tried it. I've done some of the groups just to see and I definitely see a little bit of uplift.
But I don't know, I just feel like in the long run hurts. I don't want to be dependent on that. And if video is going to win, it's going to win. It might be a little bit harder and some of that might just give me a tiny bit of an edge. But I don't think it's worth enough edge to go into it. So for me I stick away from it and just keep it natural. But I'm sure there's people who see us and we like, and we like some of their posts and they like us back. But I'm not out there in any of those commenting groups where you put it down and they share your posts.
I feel like at some point they could crack down on it or oh, the risk just isn't worth the reward, I would say.
Awesome. Yeah. And, and for anyone who's, who's thinking about that, that's like kind of where you've got these engagement circles where you find a group of similar creators and everyone posts and likes and reposts your stuff. And, and, and Chris, to your point, I think, you know, thinking about how do you create content that's great and is blowing up for, because of the content that you're creating, the value providing as opposed to looking for maybe shortcuts that like could definitely work in the short term but you know, how do you build long, long term longevity into the, the content operation you're running? Right. Cool. So Chris, thank you so much for coming on. This was awesome. Love breaking down the strategy.
Now I think it's time I see a bunch of questions in the Q and A. So if anyone else has any questions about their particular workflow, go ahead and drop those. But I already see some that we're going to get started on. So let's just let's just get going here. So Ryan asks, is it fair to bundle content into these two types, chasing views and virality through entertainment versus trying to rank for high intent keywords that solve customer problems. So I guess, you know, in simple terms, how do you think about that content mix in terms of like what we were talking about earlier, going after entertainment, virality really blowing up. So your top of funnel versus your more bottle of funnel, high intent sort of queries.
You know, I think is the question how I separate it or is. Is there only two.
Yeah. Is it fair to just bundle content into two. Those two buckets or is there, you know, another bucket?
Well, I see it now. I can see the question, is it fair to bundle these kind of chasing these reality version? Yeah, to be honest, I, I actually haven't thought of it that way, Ryan, but I would say so. I think there's. That's really the two, I guess I'm making. I'm. I'm literally. They're just trying to, to go viral and get attention or I'm trying to rank and I'm trying to. Or show people what they can do with my tool, which I'm just trying to think, you know, what I would say.
There's a third. There's a third. And that's just hopping in the conversation because there's some content I make that does really well where I'm not, I'm not like ranking or anything like that. I'm just, and I'm not talking about ClickUp, but I might just be hopping in a business conversation. So I might just be like, hey, here's a better way that, you know, you can use this technique or whatever to be better at your job or so, you know, breaking, breaking down things that make people better at their jobs. I think there's also like teaching or becoming a thought leader. That's the only other one which you could kind of put in rank, but it's a little different. I think just like actually like putting content out there that makes people better at their job, I think is the only other one that I would create.
Awesome. Next one up is, let's see, you said you mix funny, relatable content with product heavy content. What do you say is a good mix of both? What's the ratio? So I mean, if we're thinking about, I guess our content funnel, what's your mix of, you know, top of funnel, middle of funnel, bottom of funnel. And how do you like, plan for that?
I guess so for me, I think of how most people consume content and I would say 75% of people when they pull out their phone and I want you to, as I say this, I want you to think about yourself. When you pull out your phone and you pull out Instagram, you pull out X. Like are you looking for, to be sold to, you know, and told about your brand? Most of the time not. There is definitely times where I want to, most of I just want to take a break. You know, I work long hours so a lot of times if I take, I just want to like, I want to chill for a second, maybe see something that's, that's different from work. And so that's what I would say. 70% of what I, when I create is, is, is that type of content right around it. 70 is a number I would say.
And then I would say the other 20% would be showing my product. Right. And I would say 10 is a mix of either like, you know, trends or that thought leadership type content that I'm speaking about. That's my mix. And I'm not saying it's perfect. I think some people should do more. We have a different goal. Like we're at a pretty big stage and we want to make sure that everyone knows who we are.
So that's why it's worth me for creating 70. If I was still earlier in the ClickUp days and you know, maybe before series A or right around series A, I would probably be about you know, 40 to 50% on the product and then maybe 40 or so I'm making content still get me attention.
Yeah, and I think that's a really important distinction because like really what we're talking about is brand marketing versus you know, more performance style marketing stuff. So like in ClickUp's position, you guys are so big that you guys really can afford to go heavily into brand. And while brand is always important, some earlier startups, you know, they can't afford to invest in brand in the same way that, you know, a scale up really can. So I think that's a really great insight for a lot of people who, so I think what we're saying is, you know, entertainment is great and it's great for, especially at the scale that you're at. But maybe if you're in the earlier stages, you're still not going to do all 100% product content because you're like, you're saying no one, no one wants to watch all of that but really being mindful of like what your content mix is for the right stage of your business journey and that that might shift as you grow. So in your stage, you guys are 70% top of funnel and then maybe like 20 middle and then 10 bottom like you had just said. But maybe early on in your journey you're more 40% top of funnel, 40% middle of funnel, 20% bottom of funnel. So that's a, that's a great way to think about and I think that's a great call out.
Chris. Okay, next, let's see. We've answered that one. Yeah, so you've kind of already touched on this, but would love to just get a little bit more clarity. So when you guys are making content, you know, how much of the time is it your staff versus like are you guys hiring actors to like come in and create these skits or are you just kind of rolling with your in house staff and be like, hey, come over here, I have a video concept for you to shoot.
Well, I've got two, two full, like literally two, two people are paid full time and this is what they do. They create, they create content. Right now they have certain goals. They need to create seven, you know, videos we post short for a week and they need to create like 1, 2 ads a week. So you know, they're creating a lot and it's kind of a whole process to have the back end and you know, sometimes we have different, different things come in. So I would say I definitely prefer having, you know, I love having the actors. I think soon most people will in some way shape or form and I like to bring in my, my employees. I can, I don't want to take away too much of their time.
Right. They're working. So my goal is not to do that. I just do it kind of. We have to for like a fill in. And if we sometimes have a shoot, the needs other actors. You know, we'll hire Lucky. We're in California so it's kind of easy to find.
So we'll, we'll hire some actors here and there and do that. But at the beginning I think you can use your in house staff, maybe find someone who is talented, get someone who's charismatic, get a good camera. I mean the iPhones are so good nowadays. You can do that too. But just start shooting like just start figuring it out. Don't let like, don't overthink it in the early days for sure.
Perfect. Let's see. Next up we've got Mitch who asks and Mitch, if you could provide some clarification here in terms of what platform you're referring to. But I'll go ahead and assume we're just talking about the ones we were talking about. So like Instagram, TikTok, LinkedIn, that sort of thing? Yeah. Do you have any, do you have any thoughts on video length when you're creating content? Right. Like, you know, I know some people try to create shorter content so people like watch it a bunch of times and like loop through it versus like, you know, longer form content, which might be harder to keep people engaged through. But if you can get people to like stay hooked, you know, oftentimes that content does really well as well.
So I don't know, do you guys have a preference and when it comes to like length and how does that factor in your decision making process?
I'm really glad that was asked. I think a lot of people make the mistake of thinking too much about the length. And what I mean by that is some of your videos should be short, some of your videos should be long. There are some advantages to both. TikTok is now favoring videos over one minute. I know a lot of my friends are creating like one minute and one because they can run ads as soon as you go over a minute. So they're definitely favoring videos. I've seen some get a higher engagement because they have over a minute.
That being said, if the video is not good and you know, you try to make it over a minute, then no one's going to watch it. It's not going to get any views anyway. There's some videos like my, like that one, if you watch this kind of recent where they're doing the it, that's maybe like 18 seconds, right, that hit because it's like you almost want to watch it again. You're like, well those lines they said it's, it's kind of funny. So I think, don't, don't overthink. I think you should have a mix in your like because I've seen so many people like, oh, we're just going to create three, four second pieces of content because everyone had to watch it. But it's like, well, no one's going to watch it because it's, there's a thought into it. Right.
You're just putting it there. So I think don't like, there's no need to like be like we're only going to make this or that. I think when you make the video, feel it out and if you can find ways to make it shorter, I typically would, but there's some that are worth having more time if you know the pacing is there and you know the payoff is really good at the end, then you should make it longer because you're going to get more views due that watch time. So really being aware of what type of video creating, being honest with yourself, like, are people really going to watch this one then? Probably not. Then we need to shorten it up, maybe even cut a whole scene out.
Awesome. And Chris, my, my last question for you is like, what do you guys have, you know, coming up? Like we said, content's constantly changing, the goal posts are constantly moving, your targets are constantly going up. You know, you're looking for other platforms. I know we talked a little bit about YouTube but you know, in terms of you and how you're thinking about content in 2025 and beyond, what are, you know, how are you thinking about it, what are some of your focuses and what are you going to be doing differently than maybe you've, you've, you've been doing?
Yeah, look, we're going. What got us to 200 million impressions won't get us to 300 million. So I am testing a lot of new things. I want to get good at YouTube. I think learning YouTube long form and YouTube shorts and mastering that will really help me get there because I think I have mastered the Instagram, TikTok game, LinkedIn. I think you can only give us so many impressions. I'll be strategic with how much time I put into there and, and hitting on that. I think the next real thing is, is creating content where it's like episodes but short.
There's an app called Real Short. I've seen a lot of people dominating on. It's big in China and I think Quibi tried to do it but it's a little too early. So I'm not saying it's going to be the next thing, but I'm saying I'm going to test and make sure so if I can be ahead of it. So you know, like you could watch like a whole season in eight minutes, right? Like maybe it's like you have a, just one minute episodes or two minute episodes. Something like that I think could be coming because attention spans are even smaller than ever. But people do like the episodic content and format. So I will be testing that as well.
I think that's, that's the main things and I think just keep trying new shows and keep seeing what I can do to, to get attention.
Have you guys ever done anything like, I know a massive trend that's happening right now, at least in like the consumer apps world, like iPhone apps. It's like people People will get, you know, a bunch of like creator groups. They'll go be creating like hundreds of TikToks and you know, basically pumping volume and creating these like kind of groups that just go after it and, and blow up, blow things up with a bunch of volume. Is that a strategy that you guys have looked at it all, tried, experimented with, what, what do you think about that?
I'm about to try it. I'm. I'm in a contract to figure out and work with a company to try it. So let's see. I think it's like the whole micro influencer creating a lot of content. Yeah, I'll let you know. But we're in process of. We're either going to build our own machine or work with somebody who's built it before.
So we're actually like. That is something we're working on as well.
Yeah, that's, that's really cool. It's something that I know we tried in the early days. We didn't see as much success because I think inherently like product form factor is, is definitely a part of it. But again you, it's something that you really need to test at scale, I think to win. And like you were saying, when you find the concepts that work like, those can really blow up. So I think that you guys should probably pull it off and excited to see how that goes for you guys. So anyway, Chris, wanted to thank you for coming on today. This was a blast breaking down how you guys have done it.
Excited to see how you guys go from 200 to 300. You know, for anyone who's following along and wants to get in touch, learn more, follow along your journey and ClickUp's journey. Why don't you shout out your socials? Where can we follow you? You as well as ClickUp? Sure.
Yeah, I'm not hard to find. If anyone needs help, I, I'm always down to help with building social strategies. I do consulting and things like that. I'm just at Cunningham on Instagram I think on. And then on LinkedIn and Twitter it's just Chris ClickUp and I'm just chris@ClickUp.com I'm not hard to find. So if anyone wants to reach out or I can help in any way, please let me know. I had a blast. These are great questions.
I wish you all the best on your content journey. It's a lot of fun.
Thanks everyone. Really appreciate, Appreciate everyone coming to hang out. And Chris, thanks again. It was a blast.
Absolutely. Same here. Thank you everyone.
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Castmagic LinkedIn Post
Turning your content into serious business growth? That’s what every creator, founder, and marketer wants—but few master.
ClickUp’s Head of Social Marketing, Chris Cunningham, joins Blaine on Uploading to unpack the content engine behind ClickUp’s $4B brand.
Chris helped scale ClickUp from startup to a SaaS powerhouse pulling in over 200 million+ monthly impressions and building some of the most viral B2B content on the internet.
In this episode, we dig into how ClickUp’s content strategy started small and went viral, the systems and team culture powering consistent output, keys to measuring and monetizing content, and top advice for anyone looking to scale their brand with repeatable, high-impact content.
Full episode here: [link]
#contentstrategy #saasgrowth #branding #b2bmarketing #uploadingpodcast
3 quick tips
99% of brands struggle to get attention with their content.
Here are 3 proven strategies from ClickUp’s $4B content engine👇
Test Relentlessly
In ClickUp’s early days, it was all about “shots on goal.”
Try 40+ pieces. Test different styles and concepts:
• Short skits
• Music parodies
• Trending memes
• Thought leadership posts
After testing? Double down on what pops off.
Mix your content types
Don’t just chase virality. The best brands blend:
• Entertaining, viral videos (to get attention)
• Product walk-throughs (to educate)
• Insightful carousels (to build authority)
• Relatable skits (to boost shares)
Your ratio should adapt as you grow.
Early days? More product. At scale? More brand.
Build a content assembly line
Don’t do it all yourself. ClickUp’s playbook:
Host a “writer’s room” every Monday for ideas
Pick the best scripts Tuesday
Shoot every Thursday
Hire (or contract) creators, not just employees
Consistency > Perfection.
Volume + iteration = Outlier results.
Bonus:
Block time for content creation—schedule it just like any other meeting.
The $4B takeaway:
Treat content like a product. Test, iterate, and build a repeatable engine.
Steal these frameworks, and watch the impressions roll in.
1 Hack 3 tips
Here’s 1 system ClickUp used to build a $4B content engine (you can steal this for your brand):
The “Writer’s Room” Content Machine
Most brands treat content like an afterthought.
ClickUp built theirs like a TV show.
Here’s the playbook Chris Cunningham (Head of Social Marketing & founding member) shared on Uploading:
• Team brainstorms content every Monday (Writer’s Room style)
• 9+ ideas get pitched and punched up
• Thursdays = shoot day (batch filming 7–9 pieces)
• 2 full-time creators act as the “faces” of the brand
• They test EVERY idea (raps, skits, viral trends, product demos—nothing’s off limits)
Here’s why it WORKS:
“Shots on goal” mentality: Most content flops. ClickUp expects it, and out-experiments everyone else.
FORMULA gets refined: After 40 posts, review the hits. DOUBLE DOWN on what works, iterate, repeat.
Entertain first, sell second: 70%+ of content is funny, relatable, and designed to get shared—even if it isn’t “product-y.”
Product comes later: Once you have attention, layer in bottom-of-funnel demos, value props, and retargeting.
The result?
• 200M+ monthly impressions
• Content that closes deals with VaynerMedia and gets execs from massive brands into their DMs
• Fans who actually want to see “the HR guys” (their actors) more than another boring SaaS post
Want to apply the “Writer’s Room” model?
Step 1:
Block time for content—treat it as a priority, not a “nice-to-have”. (Chris literally schedules his own shoot/edit sessions weekly.)
Step 2:
Test every format.
Funny skits. Memes. Trends. Explainers. Product walk-throughs.
If it flops? Good. Now you know.
Step 3:
Get faces for your brand.
Full-time creators > random employees. (But in the early days, just start with whoever can act on camera.)
Step 4:
Review, refine, repeat.
Find your “HR Guys.” Find the format you can own. Make it a show.
Step 5:
Start EVERY piece with your ICP’s pain or humor.
Generic = invisible. Relatable = viral.
It’s about building a content ENGINE—not just posting once and praying.
For B2B, brand, or anyone scrapping for attention:
Stop winging content. Build your own writer’s room.
Steal the ClickUp playbook.
(Content compounds. And consistency = exponential results.)
ℹ️ Introduction
Welcome to another episode of Uploading..., where we dive into the biggest strategies behind today’s most impactful content engines. In this episode, your host Blaine is joined by Chris Cunningham, a founding member and Head of Social Marketing at ClickUp—the AI-powered productivity platform valued at over $4 billion.
Chris takes us behind the scenes of ClickUp’s explosive content growth, revealing how a small, scrappy team grew into a viral B2B SaaS brand, generating over a billion impressions in 2024 alone. We’ll break down the pivotal moments that shaped ClickUp’s approach, from the earliest experiments to the decision to build an in-house creator team. Chris shares the repeatable systems, creativity-improving rituals, and strategies that helped ClickUp balance entertainment with brand messaging—all while driving real business results.
Whether you’re a solo creator, part of a marketing team, or building your brand from scratch, this episode is packed with actionable advice on scaling content, measuring success, and staying ahead of the curve in today’s social media landscape. And don’t miss out—Blaine also announces the launch of a brand new, vetted Uploading community to help you connect with top creators and scale your own journey.
Let’s dive in and discover how ClickUp turned their content playbook into a $4 billion engine.
💡 Speaker bios
Blaine Bio – Sample (Summarized Story Format):
Blaine is the energetic host behind "Uploading," a platform dedicated to empowering content creators and building strong personal brands. Passionate about community, Blaine has recently announced the launch of a new, private forum where creators can connect, learn, and grow alongside some of the best names in the industry—many of whom have appeared on the show. Committed to quality and collaboration, Blaine’s community is free but selective, seeking serious creators who are ready to invest in themselves and support others. Whether you're looking to scale your content, sharpen your focus, or boost consistency, Blaine’s mission is to help you succeed every step of the way.
💡 Speaker bios
Chris Cunningham is one of the original four founders of ClickUp. His entrepreneurial journey began in Charlotte, North Carolina, where he and his team first launched a successful agency. Driven by ambition, Chris and his crew soon set their sights on bigger challenges, developing a social media app called Memory—a direct competitor to Snapchat. Memory was designed to preserve users’ memories, offering an alternative to Snapchat's fast-disappearing messages. Building on these experiences, Chris and his team eventually went on to create ClickUp, marking the start of a wild and exciting ride in the world of tech startups.
💬 Keywords
Sure! Here are 30 topical keywords that were covered in the transcript:
personal brand, private community, content creators, B2B SaaS, ClickUp, social marketing, AI productivity platform, impressions, viral content, content strategy, content systems, team culture, content measurement, content monetization, Super Bowl ad, inbound leads, outbound sales, content creators hiring, writers room, vetting process, omnipresence, product marketing, thought leadership, LinkedIn content, TikTok, Instagram, YouTube, content funnel, brand awareness, top of funnel content
📚 Timestamped overview
00:00 Chris Cunningham, head of social marketing at ClickUp, discusses the evolution of ClickUp's viral content strategy, from small beginnings to over a billion impressions in 2024. The workshop covers content systems, team culture, measuring success, and monetization, offering advice for scaling content into business.
04:14 The text describes a shift from traditional sales to leveraging content to generate leads and business growth. Initially lacking traction, the approach evolved over time to drive significant impressions and inbound growth for the company.
07:21 The goal is to entertain, gain views, and build brand recognition for ClickUp by using various content forms like scripts and videos.
09:53 Machine gains attention, closes leads, and uses personalized videos to help close deals.
13:16 Consistency is crucial; regularly block time to create videos to avoid falling behind.
19:29 The execution involves a collaborative, writer's room-style approach, working with creators, self-producing videos, and creating graphic content.
22:34 How would you start and grow a brand from scratch with minimal resources?
24:42 Success in going viral involves a formula of continuous creation, testing, learning, and iteration.
28:29 Focus on creating content for your target audience that is engaging and shareable, rather than just promoting your product.
32:18 We're at 80k on YouTube, using it mainly as a middle funnel for ClickUp tutorials. Our YouTube shorts have limited impact, but I'm consulting experts to improve and aim for 300 million views.
35:10 Q&A session begins; Ryan asks about balancing content for entertainment/virality versus targeting high intent keywords to solve customer problems.
38:46 Distinguish between brand marketing and performance marketing; large companies can focus more on brand, while startups must balance content strategies according to business stage and growth.
42:37 Make engaging, thoughtful videos; quality trumps length for viewership.
43:06 Be flexible with video length based on pacing and payoff, aiming for engagement and watch time. Adjust accordingly to audience interest.
46:34 Available for social strategy consulting; contact via Instagram (@Cunningham), LinkedIn, Twitter (Chris ClickUp), or email (chris@ClickUp.com).
📚 Timestamped overview
00:00 Scaling ClickUp's Viral Content Strategy
04:14 "Content-Driven Sales Transformation"
07:21 ClickUp's Messaging Strategy With Creators
09:53 "Effective Marketing & Sales Strategy"
13:16 "Consistency in Content Creation"
19:29 Executing Creative Video Concepts
22:34 Starting a Brand from Scratch
24:42 "Formula for Going Viral"
28:29 Audience-Centric Content Creation Strategy
32:18 YouTube Growth Strategy Discussion
35:10 Content Strategy: Virality vs. Intent
38:46 Brand vs. Performance Marketing Strategies
42:37 Optimize Video Length Strategically
43:06 Optimizing Video Length Strategically
46:34 Contact Chris for Social Consulting
❇️ Key topics and bullets
Absolutely! Here is a comprehensive sequence of topics covered in the transcript, with sub-topic bullet points under each main topic:
1. Introduction and Community Announcement
Announcement of the new, private Uploading community for content creators and personal brand builders
Details on community access, vetting process, and value for serious creators
2. Meet the Guest: Chris Cunningham and His Role at ClickUp
Chris’s background and entrepreneurial journey before ClickUp
Founding ClickUp and the transition from sales to social marketing
Early experiences as a first sales rep, customer support, and marketer
ClickUp’s evolution into a $4B AI-powered productivity platform
3. Origins of ClickUp’s Content Strategy
Starting lean with low-budget, experimental "shots on goal"
Chris’s initial content formats (e.g., videos, raps)
First major pivot: hiring an expert content creator (Luke) and scaling up
Importance of measurable bets and incremental investment in content
4. Growth and Systemization of the Content Engine
Building a repeatable content system: daily shooting and content iteration
Hiring and working with internal content creators and actors
Creating a “writer's room” structure with ideation, pitching, and production
5. Content Strategy and Platform-Specific Approaches
Tailoring content to each platform (LinkedIn, Instagram, TikTok, X/Twitter, YouTube)
Entertaining, top-of-funnel content vs. product-driven, educational, or bottom-of-funnel content
Using humor, relatability, and trends—balancing product demo content with entertainment
6. Integrating Content into the Growth Funnel
Role of content in driving brand awareness, lead generation, and sales
Retargeting strategies using familiar on-screen personalities
Use of QR codes and personalized content for sales enablement
Case study of closing major deals through social media discovery
7. Operations: Workflow and Team Collaboration
Scheduling, batching, and prioritizing content creation
Leveraging AI tools (like Claude) for repurposing, scripting, and editing
Importance of prioritization and consistency in personal and brand content
8. Content Formats and Examples
Breakdown and live show-and-tell of ClickUp’s Instagram and LinkedIn feeds
Use of repeatable formulas (e.g., HR skits, trending formats, man-on-the-street)
Experimentation and analysis of content performance by channel
9. Executing at Scale: Building a Content Team
The structure, roles, and processes: in-house creators, actors, editors
Balancing in-house staff appearances vs. dedicated creative talent
Use of office employees and occasional contract actors
10. Recommendations for Small Teams and Solopreneurs
Building in public and documenting the entrepreneurial journey
Leveraging early team members and hiring emerging creators
Testing, iterating, and optimizing content with limited resources
11. The "Viral Formula": Ideation and Measurement
Elements that contribute to virality: relatability, nostalgia, shareability
Framework for brainstorming and producing share-worthy content
Importance of knowing and targeting your ICP (ideal customer profile)
12. Platform-Specific Best Practices
Manual vs. scheduled posting and its impact on performance
Analytics, engagement groups, and the pros/cons of shortcuts
Choosing the right mix of channels for your content strategy
13. Content Mix and Funnel Ratios
Recommended mix for entertainment, product, and thought leadership content
Adjusting content ratios based on business stage and objectives
14. Future Trends and Expansion Plans
Moving toward YouTube/long-form episodic content as next frontier
Experimenting with new platforms, formats, and micro-influencer strategies
Continual testing of new approaches to hit ever-increasing impression goals
15. Audience Q&A
Content buckets: virality vs. intent-based content
Ratio and strategic mix of content types
Thoughts on engagement pods and platform specifics on scheduling
Video length, format testing, and cross-platform adaptation
16. Closing Remarks
Where to follow Chris and ClickUp online
Offer for consulting/support and encouragement to content creators
Let me know if you’d like this sequence refined further, specific timestamp breakdowns, or deeper dives into any section!
❓ Questions
Absolutely! Here are 10 discussion questions based on this episode of "Uploading...," featuring Chris Cunningham from ClickUp:
Chris talked about the “shots on goal” mentality. How do you balance taking lots of creative risks with being intentional about budget and resources when building a content engine?
The ClickUp team made an early bet on hiring full-time content creators and even actors. What are the pros and cons of investing in dedicated talent for your content versus relying on existing team members?
ClickUp’s content strategy shifted from founder-led videos to a ‘writer’s room’ approach. How might this collaborative model change the quality or diversity of content a brand produces?
Chris mentioned separating content by platform, with more thought leadership on LinkedIn versus entertainment skits on Instagram and TikTok. What are some ways to tailor content to different platform audiences without losing brand consistency?
Measurement and ROI came up frequently—what are some creative ways to directly connect top-of-funnel content (like funny videos) to actual business metrics and leads?
How important is it for founders and leaders to be part of the content creation process, and how can you encourage participation across your team without it feeling forced or overwhelming?
The episode highlighted the value of building in public, especially for startups. What does ‘building in public’ look like in practice and what risks or rewards come with this approach?
Chris described going viral as almost formulaic, emphasizing relatability, shareability, and targeting ICP (ideal customer profile). Do you agree there’s a repeatable formula to virality? Why or why not?
The team experiments with video length, trends, and formats—from music parodies to man-on-the-street interviews. How do you decide when to double down on a successful format versus pivot to something new?
As ClickUp scales and approaches broader goals (like 300 million monthly impressions), Chris discussed iterating on both content and channels. What challenges arise when trying to scale content volume and quality simultaneously, and how do you avoid burnout or creative stagnation?
Feel free to use these to spark conversation in your group, classroom, or team meeting!
🎬 Reel script
Just wrapped an amazing session with Chris Cunningham, the mastermind behind ClickUp's $4B content engine. We broke down exactly how ClickUp went from scrappy beginnings to a viral B2B content powerhouse pulling in over a billion impressions this year. Chris shared real, actionable insights on hiring creators, building repeatable systems, and mixing viral entertainment with product-driven content to drive serious business results. If you’re serious about scaling your content and turning views into value, you’ve got to check out Chris’s playbook. Follow for more content growth strategies!
🔑 7 Key Themes
Absolutely! Here are 7 key themes from the episode:
Building a scalable content engine
Hiring and leveraging in-house creators
Mixing entertainment and product content
Omnipresence across multiple social platforms
Testing, iterating, and doubling down on winners
Aligning content with business goals and funnels
Creating efficient, repeatable content systems
🎠 Social Carousel
10 Tips Every Content Marketer Needs to Know
Swipe ➡️ for ClickUp’s secrets to building a $4B content engine
1. Take Shots
Test many content ideas (shots on goal) cheaply and quickly. Double down on what actually performs.
2. Start Scrappy
In the beginning, do it all yourself—film, edit, and experiment before bringing on experts or big budgets.
3. Hire Creators
Invest in real content creators, not just internal employees. They elevate quality and consistency.
4. Make it Relatable
Create funny, shareable content that connects emotionally—or nostalgically—with your ideal audience.
5. Platform-Specific
Tailor your content style to each platform—what works on TikTok won’t always work on LinkedIn.
6. Mix the Funnel
Balance top-of-funnel entertainment with educational and product-driven posts for conversion.
7. Iterate Ruthlessly
Review data, remix what works, cut what doesn’t, and keep your ideas fresh weekly.
8. Batch & Block
Batch-shoot content once a week, then edit and schedule—you don’t need to film daily to stay consistent.
9. Go Human, Not Just AI
AI can support, but human ideas drive real virality—especially for humor and trends.
10. Build in Public
Share wins and struggles transparently—building in public makes your audience invested.
Ready to level up your brand’s content?
👉 Join our free community or DM for more content growth tips! #UploadingPod
💎 Maxims
Absolutely! Drawing from the wisdom and strategies shared in the podcast episode “The Playbook Behind ClickUp’s $4B Content Engine,” here are some maxims to live by for anyone building a content-driven brand, business, or personal mission:
Content, Creativity, and Consistency
Block Out Time—Don’t Make Excuses: If you’re not creating content, you’re just not prioritizing it. Schedule your creative time like any other meeting or task.
Consistency Compounds: Small, repeated actions (like weekly content sprints) build momentum and drive exponential results over time.
Just Start—Don’t Overthink Early Days: In the beginning, quantity and testing matter more than perfection. Don’t let overplanning stall you.
Treat Content as a Task, Not an Afterthought: Make content creation a core part of your workflow, not something you’ll “get to later.”
Iterate, Test, Repeat: The path to virality or effectiveness runs through relentless experimentation and iteration. What works gets doubled down.
Teamwork & Talent
Surround Yourself with Experts: Don’t be afraid to bring in or collaborate with creators who are better at content than you are.
Build a Creative “Writer’s Room” Culture: Regular brainstorms, open pitching, and collaborative punch-ups lead to better ideas and stronger execution.
Empower People to Do What They Do Best: Hire for specific creative or content skills rather than burdening reluctant employees with extra tasks.
Strategy & Brand
Play the Omni-Platform Game: Be where your audience is, but start with one or two key channels and expand as you master new platforms.
Shoot Calculated, Low-Budget Shots on Goal: Take lots of “bets” or experiments, but manage risk with lean, creative approaches.
Let Your Brand’s Voice Evolve: Start simple but continually refine your message, style, and platform mix as you grow.
Measuring Value
Track What Matters—Especially Shares: Shares are a deeper indicator of impact than likes. Optimize for content people want to pass along.
Content Must Fit The Funnel: Know if you’re aiming for attention (top of funnel), education (middle), or conversion (bottom)—and plan your content mix accordingly.
Infuse Brand and Product Authentically: Entertain first, but always find clever ways to showcase your product or message.
Mindset & Growth
Think Audience-First, Not Brand-First: Design content for what your ideal user finds entertaining, useful, or shareable—not what you want to “broadcast.”
Build in Public: People love transparency and authentic stories. Share the real journey, good and bad.
Prioritize High-Quality Human Creativity over Automation: Use tools and AI to help, but the best concepts and relatability come from real humans.
Keep Learning & Stay Humble: Stay curious and always test new ideas, formats, and platforms. There’s no one “right” way.
Engagement is Earned, Not Hacked: Focus on producing compelling content instead of relying on shortcuts like engagement pods.
Celebrate Your Progress & Have Fun: Results build slowly at first, but the learning, networking, and opportunities along the way are invaluable.
These maxims not only reflect ClickUp’s journey from scrappy start to content powerhouse, but serve as a pragmatic and inspiring guide for anyone wanting to grow through content in today’s digital landscape.
Interview Breakdown
In this episode of Uploading..., ClickUp’s founding member and Head of Social Marketing, Chris Cunningham, shares the inside story of transforming ClickUp’s content strategy from humble beginnings into a $4B content powerhouse. Discover the tactical approaches and content systems powering hundreds of millions of monthly impressions—and how you can apply these learnings to supercharge your own brand.
Today, we’ll cover:
How ClickUp’s content journey started small and evolved into a viral marketing machine
Key pivots, bets, and breakthroughs that defined their content strategy and scaled their reach
Building scalable, repeatable systems—and the secrets to running a “writer’s room” for business content
Balancing top-of-funnel entertainment with product-driven content to drive real business results
Tactical advice for creators and teams looking to scale content, measure impact, and build unstoppable brand engines
Short Recap
On this episode, Chris Cunningham reveals the playbook behind ClickUp’s $4B content engine, sharing how he scaled their social presence to over a billion impressions a year with a data-driven, creator-led strategy. It’s a deep dive into building viral, repeatable content systems and a team culture that turns brand engagement into real business growth—packed with actionable advice for creators at any stage.
Short Blurb
E71: The Playbook Behind ClickUp’s $4B Content Engine
In this episode, I sit down with Chris Cunningham, founding team member and Head of Social Marketing at ClickUp—the productivity powerhouse now valued at over $4 billion. Chris pulls back the curtain on how ClickUp built a content machine that regularly brings in 200M+ monthly impressions and has generated over a billion impressions in 2024 alone.
On today’s episode, you’ll learn:
How to start scrappy and scale a B2B content engine (even with a tiny team)
The high-impact pivots and bets that shaped ClickUp’s viral content strategy
How to combine entertainment and product storytelling for brand AND business growth
Proven systems for building repeatable, engaging content (and keeping your team on track)
Why measuring, iterating, and tying content back to revenue is key (with real examples)
Fun fact: Did you know ClickUp’s first major content breakthrough came from hiring a single TikTok creator on contract—and that move ended up helping close massive enterprise deals (including VaynerMedia)?
If you’re a founder, marketing leader, or creator looking to turbocharge your content strategy and translate attention into business growth, this episode is packed with practical takeaways from one of SaaS’s fastest-growing brands.
Tune in now to get the inside playbook—and don’t forget to check out the show notes for Blaine’s new private community for content creators. Listen now!
New Idea
Idea #1: Building a Repeatable Viral Content Engine
Transform your brand’s reach by building a scalable, repeatable engine for viral content. Here’s how ClickUp put this into practice:
Developing “Shows” with Dedicated Creators:
Chris Cunningham described hiring in-house content creators (like “Luke” and “Adam,” the HR guys) whose main job is to consistently generate content. Rather than relying solely on ad hoc employee contributions, ClickUp established a creator-driven writers’ room that operates like a mini media company, churning out regular scripts, testing concepts, and iterating weekly. This factory approach turns brand content into a series of recognizable, repeatable formats that audiences look forward to.Data-Driven Testing and Iteration:
ClickUp emphasizes “shots on goal” and low-budget testing—creating 40 videos, reviewing the results, and then doubling down on the formats that work (like the recurring “HR Goes Hard” skits). By measuring likes, views, and especially shares, the team refines content formulas and ensures that winning ideas are reused and evolved for even greater reach.Top-of-Funnel Content with Funnel Retargeting:
Instead of focusing content solely on product features, the team prioritizes comedy, relatable business moments, and trending memes to attract massive top-of-funnel engagement. But this isn’t just for laughs: ClickUp directly attributes high-value deals (such as VaynerMedia) to this content-first approach, using retargeting strategies to pull viewers down the funnel with recognizable characters and personalized follow-ups.
By combining creator-led production, relentless iteration, and a full-funnel awareness strategy, ClickUp built a content machine capable of generating hundreds of millions of impressions a month—proving that a repeatable system is the backbone of any viral content engine.
1 Key Learning
Build an Agile, Iterative Content Engine
Creators and teams should prioritize rapid experimentation—taking lots of calculated, low-budget "shots on goal"—and rigorously double down on what works based on real audience feedback.
Instead of pouring resources into big bets right away, ClickUp’s approach shows that consistently testing diverse, lightweight content formats enables you to identify repeatable winners. As engagement grows, invest more in proven strategies, hire standout creators, and refine your system without overcomplicating production.
This content-first, iterative mentality empowers teams to stay nimble, learn fast, repurpose efficiently, and unlock outsized organic growth—all while keeping costs low until ROI is clear.
Hustle Thread
Tweet 1:
Chris Cunningham started as a scrappy founder in North Carolina.
He lost everything building a Snapchat competitor.
But he didn’t quit.
Today, he’s Head of Social Marketing at ClickUp—driving billions of impressions.
Here’s how he built a $4B content engine: 🚀
Tweet 2:
Meet Chris Cunningham (@ChrisClickUp), founding team at ClickUp.
From broke entrepreneur to architect of SaaS’ wildest content machine.
This is how ClickUp’s viral engine was built—one low-budget bet at a time.
Tweet 3:
After his early startup flopped, Chris and friends moved to Palo Alto.
They pivoted: built ClickUp from scratch, living in a shared house.
Total grind—he was also the first sales AND customer service rep.
Tweet 4:
Early days were tough. No big budget.
Chris tried everything: videos, raps, hustle, shot after shot.
He believed in content, not just cold calls.
His breakthrough? Betting small—hiring a single creator.
Tweet 5:
He recruited “Luke in the blue shirt”—their first comedy creator.
6 weeks in: their first viral hit (3M+ views).
The board doubled down.
Soon, a team of creators churned out daily scripts and skits.
Tweet 6:
Clicks and virality were only half the story.
It wasn’t just for laughs—ClickUp closed huge deals from social.
Chris tracked everything—from reposts to personalized videos for prospects.
Tweet 7:
By 2024, Chris’s team built a repeatable system:
Writer’s rooms, weekly shoots, omnichannel repurposing, and relentless testing.
Consistent content. Constant iteration. Laser-focused on their ICP.
Tweet 8:
From broke founder to B2B content powerhouse,
Chris Cunningham turned small bets into billions of impressions—
And proved viral content can drive real business.
Tweet 9:
If you’re just starting out?
Build in public. Make tiny bets.
Focus on consistency over perfection.
Chris did it. You can too.
🧿 Viral Breakdown & CTA
Why does your B2B content flop, even with great ideas?
Want to build a content engine that fuels brand AND leads? Here’s how ClickUp grew from scrappy posts to a $4B content powerhouse—without burning cash.
I’m sharing insights straight from Chris Cunningham, ClickUp’s Founding Team member and Head of Social—his content playbook generated 1+ billion impressions in 2024 alone. He scaled from cold calls to 200M monthly views (and counting). This is how real B2B content gets done.
So what separates a viral B2B engine from endless “meh” posts?
Let’s break down ClickUp’s 3 content engine power moves:
Take “Shots on Goal”—But Make Them Smart
You need volume to find your winners, but don’t just spray and hope. Chris’s early days? He tested raps, skits—anything to stand out, all done on the cheap. Once he found repeatable hits (think: comedy skits with real creators, not random staff), he doubled down. Don’t wait for the perfect idea—launch, track, and scale what works. Iterate relentlessly, but with intent and a clear hypothesis on what your audience cares about.Hire Real Creators, Not Just Employees
Most B2B brands shove content work onto whoever’s around. ClickUp treats content like a show: they hired dedicated actors, built a writer’s room, and set strict “production days.” If you want virality and brand love, get people who live and breathe content—don’t just pass the mic at random. Start with a single creator if that’s your budget—just prove results and ramp up from there.Mix Funnels: Entertain First, Sell Second
Almost 70% of ClickUp’s output? Relatable, funny, or industry-aware skits for top-of-funnel awareness. Entertain, educate, or empathize before you ever demo the product. The “HR guys” aren’t pitching features—they’re winning followers who later convert. Then, retarget those warmed-up audiences with contextual product bits and unbeatable ads. This balance keeps your pipeline AND your brand growing.
Want these secrets straight from unicorn founders and operators? Follow DTC Pod for more tactical playbooks like this—tune in to learn from the minds shaping today’s top Creator and Commerce content engines. Your growth starts here.
Uploading... Titles
Chris Cunningham, Head of Social Marketing ClickUp – The Playbook Behind ClickUp’s $4B Viral Content Engine
Chris Cunningham, Head of Social Marketing ClickUp – How To Build A B2B Content Machine: 1 Billion Impressions, 200M Per Month
Chris Cunningham, Head of Social Marketing ClickUp – How ClickUp Turned Relatable Skits Into Inbound Leads & $4B Valuation
Chris Cunningham, Head of Social Marketing ClickUp – Inside ClickUp’s Content Factory: Going From Zero To 1 Billion Impressions
Chris Cunningham, Head of Social Marketing ClickUp – Scaling B2B SaaS Through Comedy, Creators, & 300 Million Monthly Impressions
Twitter Post 1
This behind-the-scenes play turned ClickUp into a viral machine.
Hiring one in-house creator (not just regular employees!) led to 25M monthly views in under 2 months.
Bringing on dedicated content talent can be a game-changer for B2B brands.
Mindsets
If you’re looking to build a serious content engine (like ClickUp’s), here are 3 mindset shifts to help you get started:
💭 Shift from “big splash” thinking to shots on goal. Instead of betting everything on one expensive campaign, treat each content effort as a calculated, low-budget experiment. The more tests you run (and learn from), the faster you’ll discover what works for you and your audience.
💭 Treat content as a business priority, not an afterthought. Rather than waiting for a free moment to create, block time on your calendar specifically for content—just like any other critical task. As Chris shared, consistency compounds; the rewards for showing up regularly are bigger than you think.
💭 Focus on building systems and formulas instead of chasing trends. Virality isn’t luck—it’s iteration and analysis. Use data (like which videos get the most shares), refine winning ideas, and create repeatable content series. When you treat your content like a product—with feedback loops and ongoing improvements—you’ll see compounding results.
Want more actionable shifts and behind-the-scenes strategy? Dive into this week’s episode of Uploading for a playbook you can follow, whether you’re a solo creator or scaling a team.
Future State, 6 reasons post
In 12 months, ClickUp’s content engine generated over 1 billion impressions, broke into pop culture, and directly contributed to 8-figure deals—all with a lean team and a process anyone can replicate. But most B2B SaaS brands are still stuck in old-school content ruts: low reach, low engagement, negligible impact on growth. Here’s how you can transform your brand from invisible to irresistible—and 6 moves to get there:
BACKGROUND:
The content game has changed. For most teams, the “old school” playbook looks like this:
Old Content Engine:
Every post reads like a pitch deck.
Slow, siloed output limited to blog posts.
“Social” = irregular, safe, or stale company updates.
Marketing and sales fight over lead-gen scraps.
Top creators work with B2C brands…only.
Even Better Future State:
Viral video + memes meet B2B: high volume, high-shareability content.
Dedicated in-house creators who are part of the culture—not just borrowed talent.
Collaborative, writer’s room creativity with 7+ new assets/week.
Company execs (CEO, Heads of) join the content engine—everyone becomes the brand.
Content drives full-funnel: brand awareness, engagement, and direct inbound revenue.
Quick feedback, fast testing, and compounding content IP.
At ClickUp, repeatable, high-performing content isn’t some magic accident or just flashy top-of-funnel play. It’s responsible for landing whales (think VaynerMedia), compressing sales cycles, and creating an audience bigger than most media brands.
Here’s how ANY B2B SaaS or creator-led org can make the leap—and what I’d do if I was starting from scratch:
Here are my 6 recommendations:
Prioritize Recruiting In-House Creators
Hire content creators as a core part of your marketing team—not an afterthought, not just agencies. Make them owners, not vendors.Run Weekly Writers Rooms
Act like a media company. Brainstorm, pitch, and punch up ideas every Monday. Build recurring “shows” for your ICP, not random one-offs.Test Relentlessly—Then Repeat Winners
Publish 40+ videos before calling anything a “winner.” Double down on repeatable formats (like ClickUp’s HR Guys) that hit share-worthiness and fun.Mix Brand Content with Bottom-of-Funnel Plays
70% fun/relatable content, 20% product demos, 10% pure thought leadership. Don’t just sell—build relationships then retarget like a pro.Bring Everyone Into the Content Machine
Get execs, founders, and even users making content. Personalized videos to close deals, C-suite LinkedIn posts, and UGC for social proof.Measure by Impact, Not Just Impressions
Track leads, influenced deals, and even “soft closes” (like prospects referencing viral content). Use custom CTAs, QR codes, and retargeting—all tied back to business goals.
The end result: viral growth, engaged communities, and a content flywheel that feeds sales, hiring, product feedback, and beyond.
P.S.
How is your team building its content engine? What’s the ONE change that would 10x your reach and impact—dedicated creators, a weekly writers room, or something else? Drop your playbook below. Let’s build the next $4B content machine together. 👇
Workbook
Absolutely! Here’s a comprehensive workbook based on the episode Uploading...: The Playbook Behind ClickUp’s $4B Content Engine with Chris Cunningham and host Blaine. This workbook is designed to help individuals or teams apply the lessons from the episode to their own content or brand-building efforts.
Workbook: Building a Content Engine – Lessons from ClickUp
Introduction
This workbook takes you through the strategies and tactical steps discussed by Chris Cunningham, founding member and Head of Social Marketing at ClickUp, as he outlines how ClickUp turned its content from humble beginnings into a multi-billion dollar, high-impression engine. Each section contains prompts, exercises, and checklists to help you operationalize these lessons in your own context.
Section 1: Building Your Foundation
Exercise 1: Assessing Your Starting Point
What is the current state of your content operation? (Describe your platforms, frequency, team structure, and any existing traction.)
What’s your biggest challenge with content creation right now?
What does success look like for you over the next 6-12 months?
Section 2: The Shot-on-Goal & Bet-Making Mindset
Key Takeaway: Early-stage content is about experimentation, low-budget bets, and volume.
Exercise 2: Brainstorm “Shots on Goal”
List 10 low-cost content ideas (video, written, audio, image) that you can experiment with over the next 30 days.
Who on your team or in your network can help you produce these fast?
Assign a small budget (if any) and timeline to each.
Checklist:
[ ] Clear hypotheses for each experiment (Why might this work?)
[ ] Lightweight production (Can you make it quick & cheap?)
[ ] Commitment to volume (Aim for 20-40 pieces before assessing results)
Section 3: When to Invest in Specialists & Content Creators
Key Takeaway: Hire or contract creators for sustained, high-quality output.
Exercise 3: Evaluate Your Creator Gap
Are you relying solely on team members for content, or do you have access to professional creators?
Identify at least one creator whose style aligns with your brand and reach out for a collaboration or contract.
Outline your “bet” (e.g., "In the next 8 weeks, can this creator help us break past X metric?")
Section 4: Content Mix & Strategy
Key Takeaway: Balance viral/entertaining content with educational, product, and thought leadership types.
Exercise 4: Content Funnel Mapping
Who is your ideal customer profile (ICP)?
For each platform (e.g., LinkedIn, Instagram, TikTok, YouTube), list:
Top-of-funnel ideas (entertaining, broad awareness)
Middle-of-funnel ideas (educational, use-case, challenges)
Bottom-of-funnel ideas (product demos, testimonials, case studies)
Assign tentative ratios (e.g., 70% top, 20% mid, 10% bottom for brands at scale; see Chris’s hierarchy.)
Section 5: Repeatable Systems & The Writers’ Room Approach
Key Takeaway: Use “writers’ room” sessions, repeatable formats, formula-driven testing, and batch production.
Exercise 5: Create Your Weekly System
Block out time for ideation, scripting, and batch recording (Chris recommends a Monday pitch session, Tuesday selection, Thursday shoot.)
List team members/roles who are accountable for each step.
What “repeatable series” or characters could you develop as recurring content?
Template: Writers’ Room Agenda
Review previous week’s hits/misses
Pitch 5-10 new concepts
Select 3-5 to produce
Assign scripting roles
Block out shoot/edit slots
Section 6: Measurement, Iteration, and Scaling
Key Takeaway: Test, iterate, double down on what works, and use data for decisions.
Exercise 6: Metrics & Feedback Loops
Define 2-3 key metrics to track weekly/monthly (e.g., Impressions, Shares, Signups from content)
Use qualitative feedback (e.g., sales team anecdotes, DMs mentioning your content) as another success signal.
After 8 weeks, review: What repeated themes/formats performed best?
Section 7: Personal & Team Accountability
Key Takeaway: Prioritize content just like any other core business task—schedule it, systematize it, and don’t skip.
Exercise 7: Commitment Contract
When and how will you (or your team) block time for content creation?
Who will hold the team accountable for hitting the weekly production and publishing targets?
Section 8: Going Beyond – Testing New Platforms and Trends
Key Takeaway: Once you hit saturation, start researching new content forms (YouTube, episodic shorts, micro-influencer collectives).
Exercise 8: Next Platform Playbook
Pick one new platform or content style (e.g., YouTube Shorts, “man on the street”, micro-creator network).
Research best-in-class examples in your industry.
Plan 2-3 small experiments for next month.
Reflection & Action Plan
Summarize the 3 biggest insights from this exercise that you’ll try first.
What’s your “Big Bet” for the next quarter?
Schedule a follow-up to review results and iterate.
Resources / Further Listening
Follow Chris Cunningham: [Instagram: @Cunningham], [LinkedIn: Chris ClickUp], [Twitter/X: Chris ClickUp]
Learn more about ClickUp and their content engine at [ClickUp.com]
Listen to the full episode for voice context or additional nuance.
Congratulations! You’re now equipped to start building your own scalable, high-impact content engine—just like ClickUp.
If you’d like this in a downloadable/printable format, let me know and I can format it as a PDF or worksheet.
Tweet thread on learnings
Tweet 1:
So @ClickUp’s $4B content engine is breaking the internet right now:
🔥 1B+ annual impressions
💥 200M+ per month
🌎 Turned social into a demand machine
My biggest takeaway from @chrisclickup, Head of Social Marketing, on building a viral B2B content factory: 👇
Tweet 2:
Consistency > Inspiration
Chris blocks time EVERY week—no matter what—to shoot 4–5 videos.
Content isn’t left to “when I have time.” It’s a scheduled, recurring task, just like any other.
Consistency compounds. Missing weeks is what kills content momentum.
Tweet 3:
Your First Bet Will Probably Miss—Adjust Fast
The team made raps, skits, and random content.
Nothing hit—until Chris hired a comedic creator, then doubled down when a video finally popped.
You need many “shots on goal”—quick, cheap, and ready to pivot when you see signals.
Tweet 4:
Build a “Writer’s Room”—Not a Content Silo
Every week there’s a legit writers’ room.
9+ ideas get pitched, only the best are filmed. Regular table reads, feedback, iteration.
Content isn’t magic—it’s process, creative rigor, and iteration.
Tweet 5:
Make Top of Funnel FUN—Then Find the Business
The viral HR Guys aren’t selling ClickUp on the nose. They entertain first.
But those characters reappear in retargeting ads, demo videos, and closing deals.
Bottom line: Fun is the entry point. The funnel comes later (and sales loves it).
Tweet 6:
Test, Track, Repeat Like a Machine
Nothing is random. They AB-test hooks, content lengths, and platforms.
Vids that pop get rerun with new twists.
Custom content wins deals (even a personalized video for McDonald’s execs 👀).
Everything that works gets systematized and repeated.
Tweet 7:
Start Yourself, Then Bring in Creators
It started with scrappy, solo videos.
But Chris’s bet: every brand will eventually have in-house creators and actors.
Don’t wait until you’re “big.” One creator, then two—test, prove value, then scale.
Tweet 8:
The Ultimate Playbook:
Block recurring time—no excuses
Take cheap, fast swings
Treat content as a team sport
Entertain first, sell later
Track everything, automate what works
Creators are not optional—they’re your edge
This is how ClickUp turned content into a $4B growth engine.
Youtube Description
How ClickUp BUILT a $4B Content Engine (and How You Can Do It Too)
Unlock the Playbook Behind ClickUp’s Viral Content Machine! 🚀 Get an inside look at the strategies, systems, and creative pivots that drove ClickUp’s content engine to generate over 1 BILLION impressions in 2024—and helped them become one of the world’s top SaaS brands, valued at over $4B.
💡 Want to scale your brand and crush your content goals? Learn from ClickUp’s Head of Social Marketing and founding team member Chris Cunningham as he breaks down the exact methods he used to turn ClickUp’s humble social beginnings into a world-class, omnipresent content powerhouse.
Apply to the (FREE) Uploading community to scale your personal brand and learn from top creators: https://castmagic.io/uploading
Here’s what I’ll cover in this video:
How to Start a Content Engine from ZERO: Chris shares the behind-the-scenes of ClickUp’s earliest content moves, how they experimented with low-budget “shots on goal,” and why scrappy iteration beats overthinking every time.
From Sales to Social: Discover why inbound, content-first growth now outpaces outbound in B2B SaaS—and how to build a system that turns impressions into real business results.
The Power of In-House Creators: Learn why hiring full-time actors and writers can supercharge your brand’s voice (plus tips for finding and integrating creators into your business).
Content Systems & Culture: Get the blueprint for building a “writer’s room,” running consistent brainstorming, and producing daily viral-worthy videos—even if you’re a small team or just starting out.
Content for Every Funnel Stage: Explore ClickUp’s mix of top-of-funnel viral skits, mid-funnel product education, and bottom-of-funnel conversion strategies (including genius ways to personalize content for high-value sales deals).
How to Measure & Monetize Your Content: Practical insights into tracking, attributing, and proving the ROI of content—straight from ClickUp’s billion-impression playbook.
Going Viral (for Real): Chris reveals what makes content explode in 2024, the keys to highly shareable ideas, and why relatability > algorithms.
Content Creation Workflow: Hear how Chris and the ClickUp team batch content, leverage AI tools for scripting and repurposing, and keep their production moving—without burning out.
Scaling Up (and Starting from Scratch): Whether you’re at $0 or $4B, you’ll hear step-by-step advice for building your own repeatable, monetizable content engine, including how to build in public and attract talented creators.
PLUS: Secrets to platform strategy (LinkedIn vs TikTok vs Instagram), handling scheduling and posting, and the experiments ClickUp is running next to grow from 200M to 300M monthly views!
This is a must-watch for anyone serious about content marketing, SaaS, B2B growth, or building a personal or business brand that stands out in 2024.
Don’t miss out—hit subscribe and drop your biggest questions about content below!
—
Podcast: Uploading…
Episode: The Playbook Behind ClickUp’s $4B Content Engine
Host: Blaine
Guest: Chris Cunningham (Head of Social Marketing, ClickUp)
🔗 More resources and community info in the show notes!
Simplify
Absolutely! Here’s a simplified summary of the main ideas from the transcript:
ClickUp’s Marketing Journey: Chris Cunningham shared how ClickUp started small—originally just a few people making content on a tight budget—and evolved into a platform that now gets hundreds of millions of impressions each month. They experimented a lot, learned from what worked and what didn’t, and slowly scaled up.
Content Strategies: At first, Chris made videos himself, tried different styles (even rap), and brought in a professional creator when things needed to level up. The big lesson: Hire talented creators who know how to make engaging content if you want to stand out as a company.
Different Content for Different Goals: ClickUp mixes funny, relatable videos (to get attention and build brand recognition) with educational or product-focused content (to show what ClickUp actually does). They focus heavily on platforms where their target customers are, like LinkedIn, Instagram, and TikTok.
Consistency Is Key: They have regular “writers room” meetings to brainstorm ideas, and batch-shoot their videos once a week. Chris blocks time on his calendar to create content so consistency never slips, even if he’s busy.
Tracking Results: ClickUp measures what content performs best, then repeats winning formats. They always look at what brings real business value—such as tracking leads from viral videos or making personalized videos for potential big clients.
Build in Public: For those just starting, Chris suggests showing behind-the-scenes and being transparent about the journey. Later, as you grow, bring on creators to produce better content at scale.
Virality Formula: To create content that goes viral, focus on being as relatable, human, and shareable as possible. Look for the kind of videos people want to send to their friends or coworkers because it reminds them of someone.
Content Mix: Their current mix is about 70% fun, attention-grabbing content, 20% product-focused, and 10% trend-based or thought leadership—but if you’re a smaller company, you might want to do more product content.
No Shortcuts: They prefer to post content natively, not use scheduling tools or engagement groups, because they find better results this way.
Always Testing: Platforms and trends change, so keep experimenting, look out for new platforms, and adapt your strategies.
Let me know if you’d like an even simpler version or if you want this broken down by topic or question!
Uploading LinkedIn-YouTube
@Chris Cunningham has generated billions of impressions as a founding team member and Head of Social Marketing at @ClickUp, powering their journey to a $4B+ valuation.
Chris joins @blaine on this week’s episode of Uploading to dive into the playbook behind ClickUp’s viral content engine — from scrappy early days and hiring dedicated creators, to building brand voice, iterating on content bets, and turning entertainment into measurable pipeline.
We break down content systems, omnichannel growth strategies, and actionable advice for brands and creators aiming to scale from zero to millions (and beyond).
Full episode here: [YouTube link]
#UploadingPodcast #B2BMarketing #ContentStrategy #BrandGrowth #SocialMedia #SaaS #CreatorEconomy
5 Characteristics of Winners
Based on the insights from our latest episode with Chris Cunningham, here are five characteristics that set winning content teams and creators apart:
✅ Relentless testing—“shots on goal” mentality to iterate and find what works
✅ Calculated risk-taking—starting small, placing bets, and doubling down on traction
✅ Omnipresence—showing up across multiple platforms, tailored for each audience
✅ Process-driven creativity—building repeatable systems (like a writer’s room) for consistent, high-quality output
✅ Customer obsession—deep focus on ICP, not just chasing virality, but driving business impact
#ContentEngine #PersonalBranding #ContentWinningMoves
The Rule, The Process, Keys to Success
ClickUp’s $4B Content Strategy is a perfect example of the “Shots on Goal” rule in action.
When it comes to building a content engine, Chris Cunningham and team came at it with a simple, powerful process: prioritize taking a ton of smart, calculated shots—test, iterate, and bet on what works.
The general rule: Don’t over-invest, don’t overthink, and definitely don’t expect your first videos to go viral. Instead, focus on putting a lot of content out there (but cheap and scrappy!) and let the numbers be your guide.
For ClickUp, that meant everything from Chris making his own low-budget raps and skits in the early days, to hiring one creator, then doubling down as the content started taking off. Every Monday, they run a writer’s room to brainstorm batch ideas. Every Thursday is a full shoot day. Then it’s back to editing, testing, iterating, and pushing it live, week after week.
The process is about three things:
Relentless experimentation — get 40 videos out there, see what hits, and double down.
Mix up your content: 70% relatable or funny, 20% product-focused, and 10% educational or trending.
Don’t become obsessed with perfection—block time weekly, batch what you can, and trust the compounding effect.
The key to broader success? Build for your audience, not just for virality or vague metrics. Chris and his team constantly talk to customers, test ideas, and use their content to create genuine connections. They know most content is for top of funnel, not direct selling—and that’s by design.
Don’t try to be everything to everyone. ClickUp’s playbook says: take your “shots on goal,” have a process, iterate with intention, and build for the people who care. The rest takes care of itself.
3 bullets 3 bullets (dakota)
Most of the SaaS brands crushing 200M+ monthly impressions:
• Aren’t big-budget Super Bowl advertisers
• Didn’t start with a full media team
• Didn’t have viral creators on payroll
They just:
• Take endless “shots on goal”—and learn from each one
• Hire creators, not just employees
• Test, double down, and iterate relentlessly
Eyeballs lead to business growth. But it’s not about chasing virality for its own sake—it’s about building a machine that entertains, educates, and converts your ideal customer.
Your billion-view brand engine is more repeatable than you think.
(If you want to see what that looks like in action, check ClickUp’s feed—or listen to Chris Cunningham break it down on Uploading…)
Framework To Build From Scratch
If I had to rebuild ClickUp’s $4B+ content engine from ZERO, here’s the playbook I’d use (this is the strategy ClickUp used to hit 1B+ impressions in 2024):
To turn strangers into followers (and followers into customers), you need 3 things:
• Get in front of your audience (top of funnel)
• Keep them coming back (relatable & educational content)
• Show them how you solve their problems (product in action)
So, how did ClickUp do this—and how can you?
By building your OWN content machine with these strategies:
Test Relentlessly (Shots on Goal)
Take as many “shots” as possible. Low-budget, fast iterations. 40 days of testing different styles—from funny skits to trending topics to simple relatable posts.Bring in Creators, Not Just Marketers
The best B2B brands now have dedicated, in-house creators. Hire for talent, not just resumes. Give them room to experiment.Play the Content Mix
70% Entertaining/Relatable:
– Workplace humor
– Skits about your ICP’s daily life
– Trending formats
20% Product-Focused:
– Show your tool in action
– Customer stories
10% Thought Leadership:
– Founder/CEO POVs
– Share real lessons
Mix & match for every platform—LinkedIn isn’t TikTok, and vice versa.Repurpose & Personalize
Turn one shoot into 5+ assets.
Send custom videos to high-value leads.
Leverage AI for captions & repurposing, but keep core creative HUMAN.Build In Public
Own your story—even if it’s messy. People want transparency and behind-the-scenes.Measure & Iterate
Chase shares, not just likes.
Track bottom-of-funnel: QR codes, custom links, feedback from sales. Virality is great—conversions are better.
Bottom line: Consistency beats perfection. Volume leads to breakthroughs. Don’t talk AT your audience—create FOR them.
Start stacking these pillars and you’ll build a content engine that drives real business, not just vanity metrics.
(P.S. If you want to see real examples, check ClickUp’s Instagram or LinkedIn. It’s all there.)
3 Success Strategies
Lean Into Repeatable Content "Shows"
Instead of relying on a handful of one-off viral hits, the ClickUp team treats content creation like building out a TV lineup—with repeatable “shows” starring memorable personalities. Chris Cunningham’s playbook is simple: Identify formulas that resonate (like the “HR Guys” sketch series) and double down. Regularly test dozens of concepts, then refine and repeat top performers on a predictable schedule. Viewers know what to expect, start to anticipate the next episode, and your content operation becomes easier to manage and scale. When your audience can’t wait for the next installment, you know you’re building something sticky.Test Relentlessly, Iterate Without Ego
If you want to drive 200+ million monthly impressions, you can’t afford to rest on old ideas—or your laurels. Chris emphasizes the importance of putting constant “shots on goal,” but always with small, calculated bets and low budgets. Early on, ClickUp’s content didn’t have a magic formula. It was a whirlwind of experiments: raps, skits, and homegrown videos. Only by rigorously testing (40 posts before evaluating a new series!) and closely analyzing what hit—and why—were they able to uncover repeatable winners. Don’t get attached to your favorite ideas. If the data doesn’t back it, move on. Consistent iteration is how you transform random hits into a viral machine.Build for the Entire Funnel, Not Just the Feed
The most successful B2B content engines look beyond raw likes and top-of-funnel engagement—they architect their output for every stage of the buyer journey. For ClickUp, that means a healthy mix of viral, entertaining skits to drive brand awareness; thought-leadership and value-add content for consideration; and smart call-to-action tactics like product demo videos, QR codes, or custom assets for hot prospects. When a viral character (like the HR guys) is already loved by your target customer, retargeting becomes cheaper and more effective. Think of content as the connective tissue across your funnel—capable of creating leads just as efficiently as a high-performing outbound sales team, but with exponentially greater scale and resonance.
3 Success Strategies v2
Build Your Content Engine Like a TV Show
Think your B2B brand is too “boring” to go viral? Chris Cunningham’s playbook at ClickUp proves otherwise. One of his game-changing strategies is to treat content creation like running a TV show: every week, there’s a writer’s room, a slate of new ideas, a production schedule, and a team that’s constantly iterating.
Here’s how Chris pulls it off:
Weekly writer’s rooms: Every Monday, the team gathers to brainstorm and pitch nine or more video concepts, just like a comedy show’s writers would.
Punch-up, refine, and prep: On Tuesday, the team chooses the winning ideas and refines scripts, ensuring that only the strongest—and most shareable—survive.
Batch production: Thursdays are for shooting. Dedicated creators spend the whole day filming, ensuring there’s a steady pipeline of content to test and publish.
What does this look like in action? Relatable “HR guys” skits, trending audio rewrites, and rapid engagement with business culture moments—all created with a repeatable, collaborative system.
To get started, gather your marketing team (or just your most creative colleagues!) and block off time to brainstorm together. Build a lightweight weekly workflow for ideas, refinement, and production—even if you’re just working with a smartphone and a couple of enthusiastic teammates. Consistency and collaboration are what drive the content machine forward.
Bet Small, Iterate Fast, and Double Down on Winners
Forget “big bang” campaigns that drain your budget with no guarantees. Chris’s take: treat every new content idea as a bet—start small, launch quickly, and let data decide what gets more investment.
Here’s how ClickUp’s betting system works:
Low-budget, high-frequency experimentation: Launch content ideas with minimal costs, whether it’s a new video series or a trending format.
Face quick feedback head-on: Track performance within six to eight weeks. If a piece starts to outperform—say, nabbing millions of views—secure more resources and scale up.
Repeat successful “shots on goal”: Chris’s team doesn’t shy away from remixing and repeating formats that are proven hits (like their HR dance sketches), adapting cadence to avoid audience fatigue.
In your own practice, this means keeping content costs flexible, launching ideas often, and doubling down only when something clearly resonates. It’s a process rooted in rapid testing rather than guesswork or arbitrary deadlines.
Use simple analytics to monitor what’s working, and don’t be afraid to quietly retire ideas that don’t deliver. Over time, you’ll create a content ecosystem that feels both experimental and measurable—and far more sustainable.
Connect Content to the Entire Growth Funnel
It’s easy to get caught up in making funny or viral videos and forget about business impact. Chris’s secret is integrating every piece of content into ClickUp’s full growth funnel—moving audiences from broad awareness all the way to demo bookings and closed deals.
Here’s how ClickUp does it:
Entertain to attract: Viral skits and relatable workplace content open the door, driving massive top-of-funnel impressions from wide audiences.
Retarget and educate: Anyone who engages with entertaining content is later retargeted with product-focused videos (often starring the same beloved characters), seamlessly introducing ClickUp’s capabilities.
Personalize and close: For high-value leads or deals in progress, the team crafts bespoke videos—sometimes even personalized messages from the “HR guys”—to delight prospects and nudge them toward conversion.
Chris also pulls in data from their AI tools to identify who’s following the brand, seizing opportunities for hyper-targeted outreach.
To make this work for your brand, plan your content with multiple stages in mind: what will grab attention (top of funnel), what will nurture interest (middle), and what will help close sales (bottom). Align metrics to each step and create clear handoffs from fun, shareable moments to practical product stories.
By weaving entertainment and education together—and keeping everything tied to concrete business goals—you’ll ensure your content engine doesn’t just go viral, but drives real growth.
Episode Summary
Chris Cunningham is a founding member and the head of social marketing at ClickUp, the $4B AI-powered productivity platform. Since joining the company in its early days, Chris has been instrumental in developing ClickUp’s brand voice and transforming its social channels into a powerhouse content engine, consistently generating hundreds of millions of impressions monthly. His innovative approach includes building in-house creator teams, leveraging viral video formats, and blending B2B thought leadership with entertainment-driven content.
In this episode of Uploading, Chris breaks down the content strategies and systems that turned ClickUp from a scrappy startup into one of the most influential names in B2B SaaS. He shares actionable insights on assembling creator-led teams, testing and iterating content formats, measuring ROI, and integrating content seamlessly across the funnel—from top-of-funnel brand plays to bottom-of-funnel conversion tactics. The discussion also covers advice for brands starting from zero, building a culture of creativity, and scaling content operations for maximum business impact.
Blaine Content Sample
How ClickUp Grew Their Content Engine to 200M+ Monthly Impressions (and What You Can Steal)
A few years back, ClickUp’s social media presence looked like everyone else’s—it was just getting off the ground, scrappy, and nowhere near the billion-impressions mark they’re now hitting in 2024.
Fast forward to today: ClickUp is raking in 200M+ impressions every single month, their content is everywhere (literally omnipresent), and they’ve built an engine that not only grows the brand but actually drives real leads and business.
Here’s a peek behind the scenes on how Chris Cunningham (founding member + head of social at ClickUp) and team did it, plus the principles you can use to scale your own content game.
Background
Started with zero traction & no fancy team—just hustle, trial-and-error, and tons of “shots on goal”
Treated content as a repeatable, test-driven system (not just “one-off” viral moments)
Focused on hiring actual creators, not just asking employees to moonlight as content folks
These are the big 4 principles that powered ClickUp’s content engine:
Shots on Goal (but Make Them Smart)
In the early days, it was all about volume—but with intention and minimal spend. Chris would run tons of low-cost experiments (sometimes even rapping on camera himself) just to see what stuck. Most didn’t blow up, but every experiment was a learning loop.
When they found the right formula (i.e., hiring a dedicated creator with a proven track record), they doubled down and scaled it: think “one big bet at a time,” always keeping budgets tight and impact measurable.
Omnipresent by Platform & Persona
What wins on TikTok isn’t what wins on LinkedIn (or X, or Instagram), so they didn’t force-fit one style everywhere. Instead, the team built “shows” and personas for each channel—comedy for IG, thought leadership for LinkedIn, and tested which segments performed where.
Repeatable formulas (like “HR Guys”) were systematized, and if a bit went viral, they’d remix or rerun it with variations, balancing top-of-funnel awareness and middle/bottom-funnel conversion plays.
Relentless Iteration & Feedback Loops
Every week is a new writer’s room, new ideas, new tests. If it works, do it again (but not too often, or you run it into the ground). If it flops, tweak and retool. Every video, post, or campaign gets rated, analyzed, and either doubled down on or put on ice.
And yes, consistency is everything: they block time, batch-create assets, and leverage AI tools to repurpose snippets across channels (without sacrificing originality).
Don’t Just Entertain—Integrate With the Funnel
Fun skits and viral moments are great, but it’s all connected to pipeline. ClickUp consistently weaves product touchpoints into entertaining formats, tracks leads via QR codes or DMs, and uses custom content to help sales close big deals.
When sales teams flag a hot prospect, the content team will even whip up bespoke “HR Guys” videos to push things across the finish line. (Personalization > cold emails, every time.)
The Content Split That Works:
70% top-of-funnel entertainment/brand
20% product-led or middle-funnel
10% bottom-funnel/explicit pitch (but this shifts as your company matures)
What’s Next?
ClickUp’s always hunting for the next “big show”—shifting to YouTube, experimenting with episodic short-form, and testing micro-influencer networks. The process is never finished, but that’s what keeps their engine spinning.
Key Takeaways For Your Own Brand:
Treat content as an engine, not one-offs: systematize your process, iterate fast
Hire or work with actual creators—quality shines through
Mix entertainment with education and product, but always tie back to your funnel goals
Be obsessed with feedback and relentless improvement
If you’re building a content engine, borrow these tactics—and go bigger on your bets with every signal you get. Would love to hear how you’re scaling your content systems!
1 most actionable piece of advice
Block out weekly time to consistently create and batch content.
Gregs LinkedIN Example
the $4B content engine playbook (the ClickUp edition)
start lean: you’re the sales rep, marketer, and creator
take constant shots on goal—iterate fast, test cheap
hire creators, not just employees—turn your office into a studio
scale with repeatable “shows” & characters (think HR Guys, inside jokes, skits)
mix brand and product: 70% relatable bangers, 20% product, 10% thought leadership
build in public—audience loves the journey, not just the result
weaponize relatability—content = shares = impressions = leads
treat content as another task—batch, block time, keep it non-negotiable
viral is a formula: strong hook, deep human insight, perfect shareability
amplify with AI for copy, not for concepts—your brain, Claude’s keyboard
old b2b playbook: cold calls and outbound sales
the new playbook: viral content machines + inbound mountains
to win:
ICP obsession—know who you’re creating for, inside jokes included
low budget bets (prove, then invest)
an internal “writer’s room” (Monday ideas, Thursday shoots)
omnipresence—LinkedIn, Instagram, TikTok, then layer on YouTube, X
track & monetize: QR codes, retargeting, personalized videos
2023: “every company needs a sales team”
2025: “every company needs creators on payroll”
ClickUp did it:
1 creator → 25M monthly views → full team → 200M+ impressions/month
content closes deals (ask VaynerMedia, GaryVee saw the posts)
don’t overthink gear—iPhones and office staff can go viral
virality? Shares > likes, always
Pro tip: Scaling?
Early: 40% product, 40% entertainment, 20% authority
Growth: 70% banger, 20% product, 10% trends/education
You can build a viral content engine with less than you think.
Start with shots on goal.
Find your HR Guys.
Iterate, punch up, post.
Happy uploading.
Questions Shownotes
How did ClickUp’s content engine evolve from humble beginnings into a viral B2B powerhouse?
What was Chris Cunningham’s journey from founding an agency and failed social app to building ClickUp?
Why did ClickUp initially decide to take a “shots on goal” approach with their early content?
How did hiring their first full-time content creator transform ClickUp’s brand and social media strategy?
What was the breakthrough moment that proved the ROI of ClickUp’s content investments to leadership?
How does Chris design repeatable, scalable content “shows” to consistently reach hundreds of millions of impressions?
Why does Chris believe every modern brand will need to hire dedicated content creators to compete?
How does the content strategy differ between platforms like LinkedIn, Instagram, TikTok, and X (Twitter)?
What roles do entertainment, education, and direct product promotion play in the overall content mix?
Why does ClickUp incorporate skits, humor, and relatable workplace scenarios in their videos—and how do these drive inbound leads?
How does ClickUp personalize video content for target clients to help close sales deals?
How does Chris and his team ensure that even busy executives (like the CEO) consistently create content?
Why is batching and blocking content creation time essential for ongoing consistency and growth?
Which content ideas and formats does ClickUp iterate on, and how do they determine what “formula” works?
What is the “ABCD formula” for content ideation, and how does it drive their testing process?
How does ClickUp adapt content for different stages of the marketing funnel, from top-of-funnel awareness to bottom-of-funnel conversion?
What metrics matter most to Chris when measuring content success—and why do shares beat out likes?
How should early-stage founders and small teams approach content creation before they have ClickUp-scale resources?
How is ClickUp planning to scale from 200 million to 300 million monthly impressions, and what new trends are they experimenting with?
What actionable advice does Chris offer to creators and marketers who want to build, measure, and monetize their own content engines?
Episode summary
Chris Cunningham is a founding member and Head of Social Marketing at ClickUp, the AI-powered productivity platform valued at over $4 billion.
In this episode of Uploading, Chris takes us inside ClickUp’s $4B content engine, revealing how they scaled from scrappy beginnings to over a billion impressions in 2024. He shares the playbook for building viral B2B content, key pivots that shaped their strategy, and how he built a team and culture that consistently delivers results. Plus, Chris breaks down ClickUp’s approach to balancing brand and performance content, building repeatable systems, measuring ROI, and actionable advice for creators looking to turn content into business growth.
Lead Magnet Idea
Lead Magnet:
"Build Your B2B Content Engine: The ClickUp Playbook for Viral Growth"
Description:
This visually compelling, easy-to-follow PDF guide is your actionable blueprint for transforming your B2B content strategy—taking direct inspiration from Chris Cunningham and the ClickUp team’s secrets that drove them from zero to over a billion annual impressions. If you’re a founder or marketing leader looking to scale your content, build a repeatable system, and actually tie your efforts to business results, this toolkit is for you.
Components:
1. The B2B Content Engine Roadmap
Quick primer on how ClickUp’s approach blends content creation with lead generation and revenue.
“Shots on goal” visual worksheet: Map your own low-cost, high-frequency content experiments based on what’s working for ClickUp.
2. Your First Content Creator Play
Step-by-step instructions for hiring your first (affordable) content creator or getting started solo—regardless of budget.
Sample contractor outreach email (inspired directly by Chris’ approach with Luke, the “guy in the blue shirt”).
Cheatsheet: “How to Test and Triple Down on Winning Formats” (based on the ABCD formula shown in Chris’s writer’s room process).
3. Repeatable Content Systems for Busy Teams
One-page “Content Production Sprint” template (Monday: brainstorm, Wed: scripts, Thurs: film, Fri: edit & schedule).
Tips for blocking out time, batching shoots, and using AI tools to repurpose your content for each platform.
Checklist: How to involve your team without disrupting their workflow.
4. The Viral Video Blueprint
Fill-in-the-blank scripts for highly shareable, relatable posts (steal ClickUp’s “HR Guys,” trend-jacking, and business skit ideas).
Engagement triggers: Make your video content more shareable by focusing on relatability, nostalgia, and inside jokes for your ICP.
5. Content Funnel Calculator
Visually map your Top, Middle, and Bottom of funnel content with real ClickUp-inspired examples.
Ideal content mix worksheet: Adjust percent of entertainment vs. product vs. thought leadership content for your stage.
6. From Attention to Revenue: Tracking What Works
Simple dashboard for tracking impressions, leads, and closed deals driven by content.
QR code and retargeting playbook so you can prove ROI from your creative experiments.
Sample personalized “deal closing video” template.
Bonus:
Visual gallery: 10 winning ClickUp posts (with commentary on what made each work and how to riff on them for your brand).
List of go-to low-cost creator platforms and free tools to launch your content engine now.
Visual Appeal:
Infographics illustrating “The ClickUp Impressions Engine”
Example content calendars, checklists, and fillable worksheets
Pull quotes and real screenshots from the episode to bring tactics to life
Call to Action:
Download Instructions:
Click the link below to get your free copy of “Build Your B2B Content Engine: The ClickUp Playbook for Viral Growth.”
Invitation to Engage:
Level up even faster! Join our free Uploading Community for behind-the-scenes workshops with creators like Chris, peer feedback, and live Q&A. [Link in the show notes]
Follow-Up Offer:
Want tailored advice? Book a free 20-minute strategy consult with our content experts, or grab a spot in our next “Content Engine Accelerator” cohort.
Example CTA:
Ready to turn your content into a brand-building, lead-generating machine?
Download the “ClickUp Playbook for Viral Growth” now!
Get the actionable templates, step-by-step systems, and inside tactics straight from one of SaaS’s most effective content teams.
→ [Download Now]
And don’t miss your invite to our free community for exclusive workshops, resources, and expert support—see you inside!
By drawing directly on the episode’s insights and providing tangible tools, this lead magnet equips your audience to act now—while tying them back to your brand, content, and services for deeper engagement.
5 reasons why with a PS
I grew ClickUp’s brand to hit over 1 BILLION impressions in 2024 (and we’re going for 300M per month this year). Here’s 5 hard-learned lessons behind building a content machine that actually drives business—even if you’re starting with zero budget and zero team:
Run calculated shots on goal.
Treat content like experiments. Start CHEAP, iterate fast.
Instead of “let’s make a viral ad,” try everything—raps, skits, carousels, you name it.
Betting on content means low budgets, small bets, and learning what hits (before you scale it up).
Don’t rely on “someone from the office” for content.
Hire or be THE creator, even if it’s just you in the beginning.
A killer content creator will outperform whatever random employee video your team cooks up.
We brought in Luke (aka “the guy in the blue shirt”) on a contract—and once the numbers hit, ramped HARD.
Build systems, not just one-offs.
Our process? Weekly writers’ room, ideation, punch-up, shoot day, then editors process the magic.
Make content a recurring meeting on the calendar. Consistency > one-hit wonders.
Use tools (and your product!): block out time, automate tasks, and batch-record to build a true engine.
Content isn’t one-size-fits-all.
On LinkedIn: Thought leadership, personal stories, and visuals.
On TikTok/Instagram: Funny, shareable, highly relatable bits (“HR guys”, music videos, quick skits).
Mix education, brand, and product. Only pushing product = zero reach. 70% entertainment/relatable, 20% product, 10% trends/leadership is our current mix at scale.
Track, personalize, and close deals with your content.
Get creative with attribution (QR codes, custom videos for sales prospects, even hyper-personalized shoutouts for top target accounts).
Sales team use your content as the closer—don’t underestimate inbound and retargeting value.
Content is NOT just “for fun”—it moves pipeline and closes real revenue.
You don’t need a $10M ad budget.
You just need tight feedback loops, a willingness to experiment, and a relentless, systematic approach to getting 1% better every week.
Skip the vanity—commit to the reps.
Don’t gatekeep your journey. Build in public. Show the highs and the lows.
P.S.
Want to level up your own content approach? Our new Uploading community just launched. It’s free, vetted, and focused on building your personal brand (for real, not fluff). Apply here: https://castmagic.io/uploading-community
Let’s build brands (and business) together.
Episode Notes
SUMMARY OF EPISODE
In this workshop episode of "Uploading...", Blaine is joined by Chris Cunningham, founding member and Head of Social Marketing at ClickUp—the $4B AI-powered productivity platform. Chris dives deep into how ClickUp evolved from scrappy beginnings into a content powerhouse, regularly generating over 200 million impressions a month and reshaping the game for B2B SaaS brands.
Blaine and Chris explore:
ClickUp’s journey from early failures to breakout success.
The calculated bets and strategic pivots that fueled viral growth.
Building repeatable content systems—and a team culture that keeps the engine running.
Creative approaches to measuring and monetizing content, from personalized videos to QR-coded campaigns.
Tactical advice for creators and marketing teams eager to scale their content and drive real business results.
Chris opens up about ClickUp’s “shots on goal” mentality, what it takes to build a viral content engine on a lean budget, and how to foster a team of full-time creators who operate more like a modern writer’s room than a traditional marketing team.
BULLET POINTS OF KEY TOPICS
Early Days and Pivots from Failure to Product-Market Fit
Chris recounts the journey from running an agency to launching an unsuccessful Snapchat competitor, then pivoting to build what became ClickUp. He discusses lessons learned from setbacks and how those experiences shaped ClickUp’s product and marketing DNA.
Strategic Content “Bets” & Hiring Creators [00:05:09]
Chris details the “shots on goal” philosophy—prioritizing constant experimentation with low-budget content bets. He shares why he hired a full-time creator, “the guy in the blue shirt,” after recognizing that companies would need in-house creators to stay competitive, and how this move led to breakthrough viral hits and millions of new impressions.
Building Repeatable Content Systems & Process [00:07:04]
Chris reveals ClickUp’s operational backbone: weekly writer’s rooms, batching video shoots, and assembling a team that iterates obsessively. He explains the ABCD formula for content testing, how to analyze winning posts, and the value of sticking to a cadence—even if it means blocking off calendar time and using AI tools to streamline ideation and editing.
Content Strategy Mix: Funny, Relatable, and Product-Centric [00:08:07]
Blaine and Chris break down balancing entertainment with intent: using top-of-funnel content for brand awareness alongside product-focused posts for conversions. Chris illustrates how content hooks major clients and supports sales (sometimes with personalized videos for big prospects).
Content Platform Tactics: Instagram, LinkedIn, TikTok & More [00:14:31]
Chris gives a tour of ClickUp’s video-heavy Instagram strategy, using trends, nostalgia, and “HR guys” skits to maximize engagement. He contrasts this with LinkedIn, where visual carousels and thought leadership take center stage, and shares ongoing experiments with platforms like YouTube and X.
Data, Metrics, and Attribution [00:09:53]
From QR codes to feedback loops with sales reps, Chris discusses how ClickUp ties content output to real business impact. He shares examples of deals closed after connections made through viral content and the importance of tracking beyond vanity metrics—focusing especially on shares as the metric that drives virality.
Advice for Early-Stage and Scaling Brands [00:23:26]
Chris outlines what he’d do starting from scratch: “build in public,” document the journey, leverage early team members for authenticity, then reinvest in creators as the brand scales. He emphasizes iteration, learning from the audience, and the importance of understanding your ICP.
Frameworks for Virality & Content Ideation [00:25:55]
Diving into what fuels ClickUp’s breakout hits, Chris talks about generating “human” content that’s deeply relatable, leveraging nostalgia, office humor, and attention-grabbing concepts. He shares the mindset behind crafting content designed to be shared—and why shares (not just likes) are a top KPI.
Content Mix & Funnel Balance [00:37:24]
Chris suggests a 70/20/10 content split at ClickUp’s current scale—70% entertainment/relatable, 20% product show-and-tell, 10% trends/thought leadership. For earlier-stage brands, he advocates a heavier tilt toward product until the brand matures.
Scaling Creators & Exploring New Content Models [00:41:30 / 00:45:30]
Chris discusses hiring full-time actors/creators, pulling in office staff for authentic moments, and future plans to test micro-influencer networks, episodic short-form content, and new platforms like YouTube Shorts and RealShort to sustain growth as ambition rises.
Scheduling, Engagement, and Platform Nuances [00:30:55]
Manual posting is Chris’s preferred method over scheduling tools, for better algorithmic results and personal touch—plus his take on engagement groups and the ethical balance in platform strategies.
__
This episode is packed with actionable insights for founders, marketers, and anyone hungry to build a high-impact content engine with real business outcomes. Follow Chris Cunningham (@Cunningham on Instagram, Chris ClickUp on LinkedIn/X) and ClickUp to see these strategies in action.
Timestamps Trial
00:00 Uploading Community Announcement & Episode Intro
00:46 Meet Chris Cunningham: ClickUp’s Content Architect
02:11 Chris’s Background: From Agency to ClickUp’s Founding Team
04:05 Early Content Hustle: Sales to Scrappy Content Creation
05:09 Shots on Goal: Low-Budget Bets & the First Creator Hire
07:04 Building a Repeatable Content Engine: Scaling with Creators
08:07 Platform-Specific Content Strategy & Goals
09:53 Linking Content to Business Impact & Funnel Strategy
11:28 Making Content a Team Priority: Systems & Scheduling
13:44 Consistency, Time-Blocking, and Using AI Tools
14:37 Screen Share: Inside ClickUp’s Instagram Strategy
15:38 The ABCD Formula: Testing for Virality
16:09 Case Study: Viral Skits, Trends, & Relatable Office Content
17:49 Leveraging Memes, Trends, and Episodic Content
18:59 Mixing Product & Entertainment in Content Mix
19:29 Operations: Writers’ Room, Shooting Schedule, & Execution
21:09 Getting Employees Involved & Lightweight Content Production
22:34 Adapting Content per Platform & Cross-Posting Wins
23:23 Starting from Scratch: Building in Public & Early Tactics
24:42 Hiring Creators on a Budget & the Iterative Process
25:47 Frameworks for Virality: The Anatomy of a Viral Video
27:41 Winning Concepts: Relatability, Shareability, & Emotional Triggers
29:39 Know Your Audience: Interviewing the ICP for Better Content
30:55 Scheduling vs Manual Posting: What Works Best
32:18 YouTube Strategy: Current State & Future Focus
33:36 Platform Prioritization: Focus, Layering, & Growth Sequence
34:26 Engagement Pods: To Participate or Not?
35:52 Content Funnel Mix: Brand Awareness vs Product Promotion
37:24 Content Ratio: Top, Middle, & Bottom of Funnel by Stage
40:00 Staff vs. Actors: Who Should Be in Your Content?
42:10 Video Length: Short vs Long Content & Platform Preferences
43:35 Looking Ahead: 2025 Content Experiments & New Channels
45:30 Micro-Influencer Strategy: Pumping Volume & Testing
46:19 Wrapping Up: Follow Chris & ClickUp; Final Thoughts
About the Episode
Chris Cunningham is the founding member and Head of Social Marketing at ClickUp, the $4B AI-powered productivity platform that’s become a behemoth in the B2B SaaS content space. Since 2017, Chris has been the driving force behind ClickUp’s viral content engine, leading a team that regularly generates over 200 million impressions a month and has surpassed a billion impressions in 2024 alone.
In this episode of “Uploading…,” Chris breaks down exactly how ClickUp scaled from scrappy, experimental content in a crowded market to operating a multi-channel, repeatable content machine. He shares key pivots in their strategy—including the decision to recruit full-time creators and build a writer’s room culture—plus actionable frameworks for developing viral, shareable content across platforms like LinkedIn, Instagram, and TikTok.
Chris also dives into creating content that drives real business outcomes, from attracting high-profile clients to integrating content across the full marketing funnel. Whether you’re a founder, marketing leader, or solo creator, you’ll get practical insights on team building, workflow, and using AI to maximize output—along with advice for anyone looking to scale their content and brand in today’s competitive landscape.
Show Notes
Episode Summary
Chris Cunningham, Head of Social Marketing and founding member at ClickUp, joins Uploading to reveal the secrets behind building ClickUp’s content engine—now responsible for over a billion annual impressions and helping grow the company’s value to over $4B. Chris shares lessons learned from scrappy beginnings to leading a “viral content machine,” the key bets and breakthroughs along the way, and actionable advice for creators and brands looking to scale content that actually moves the needle.
Episode Notes
About the Episode:
Chris Cunningham is a founding member and Head of Social Marketing at ClickUp, the fast-growing productivity platform now valued at $4 billion. Since shaping ClickUp’s brand voice and social presence from 2017, Chris has been instrumental in engineering a content system that regularly generates 200M+ monthly impressions and consistently translates content virality into real leads and customers.
In this workshop episode of Uploading, Chris breaks down ClickUp’s journey from early hustle—making videos solo and closing deals by hand—to building a repeatable, scalable content operation with an in-house “writer’s room,” comedic actors, and a growth strategy spanning multiple platforms.
Chris and host Blaine dive into content pivots, hiring creators, their “shots on goal” philosophy, building brand voice, and why entertainment-first content matters for B2B. Chris also gets tactical: how to mix content types across the funnel, the operational playbook for consistent output, leveraging AI tools, success metrics, and what it takes to hit massive growth milestones.
Finally, Chris shares actionable frameworks for solo founders and small teams starting from scratch—plus candid takes on virality, team structure, platform strategy, and what’s next for ClickUp’s $4B content engine.
Today, we’ll cover:
How ClickUp scaled from low-budget solo content to 200M+ impressions per month
The “bets” and breakthroughs that defined ClickUp’s content playbook
Building a repeatable system: team, workflow, “writer’s room,” and actors
Entertainment vs. product-driven content—and the ideal content mix
Measuring ROI: turning impressions and brand awareness into real leads and customers
Frameworks and advice for solo creators and early-stage teams to start content from scratch
Platform-specific strategies for LinkedIn, Instagram, TikTok, YouTube, and beyond
Personalization, AI, and creator partnerships: the new wave of B2B content
What You’ll Learn
Why B2B content should prioritize entertainment and relatability (and how it still brings in leads)
The “writer’s room” approach and cadence for producing high-volume, high-quality content
How to build a viral content formula using iteration and trends—plus operational tips for consistency
The right content mix for your stage (startup, scaleup, enterprise) and goals (brand, lead gen)
Tracking and monetizing content: how ClickUp credits deals to content, retargets prospects, and personalizes sales
Actionable steps for solo founders: building in public, hiring creators, and testing quickly on a budget
Tactical advice on content batching, AI usage, and workflow for busy execs and marketing leads
How “shots on goal,” betting small, and relentless testing underpin ClickUp’s success
Timestamps
00:00 — Intro, show updates, and today’s guest: Chris Cunningham of ClickUp
02:11 — Chris’s backstory: ClickUp’s origins, agency days, and building from nothing
05:09 — Early content strategies: shots on goal, low-budget bets, and hiring creators
07:21 — Defining brand messaging: entertainment + product, content briefs, and goals by platform
10:46 — Integrating content into the whole funnel and growth strategy
11:55 — Chris’s weekly content creation routine and tips for busy teams
14:31 — Live walkthrough: ClickUp’s Instagram & content breakdown with real examples
19:28 — Execution: writing, shooting, editing, and bringing in actors or internal staff
23:26 — How to start content from scratch as a solo founder or small team
25:13 — The formula for virality and how to brainstorm shareable ideas
28:29 — Understanding audience and ICP to drive content resonance
30:55 — Manual posting vs. scheduling tools: what works for ClickUp
32:18 — Platform strategies: LinkedIn, TikTok, Instagram vs. YouTube and what’s next
40:27 — Ratio of entertainment vs. product-driven content and how it changes as you scale
41:30 — Building a content team: actors, internal staff, and creators at scale
42:16 — Video length, testing, and best practices for engagement
44:04 — What’s next for ClickUp’s content: new formats, platforms, and tests
45:02 — Micro-influencers, scaling via creator “pods,” and new experiments
46:34 — Where to follow Chris and wrap-up
Quotes
“Shots on goal—we want to put as many shots up as possible, but we want to have calculated shots. We want to take them with low budgets...I’ll make a bet and I’ll start it very cheaply.” — Chris Cunningham
“The only way it’s really going to scale is I brought in an expert—a creator. I took a bet that all companies would have content creators if they wanted to compete. They’ll have some kind of creator that creates content for them consistently.” — Chris Cunningham
“Content's just another task, right? Like anyone can make excuses. So if you're just not making content, it means you don't prioritize it. We prioritize it.” — Chris Cunningham
“The dividends content rewards with is nuts. The amount of people I’ve met, the people who DM me and just what I’m learning...There’s no reason not to make content.” — Chris Cunningham
“If I had to start over at a new company—we’re building in public. No actors, just talking about what we’re working on. People love to see it. At the end of the day, I would just ask for like 5-10 minutes of all the early employees: what did you do today? And find a cool, clever way to chop it up. That’s exactly what I would do.” — Chris Cunningham
“You need to know your ICP. If you’re creating content and you don’t know who you’re creating for, you really just lost the whole goal right there.” — Chris Cunningham
Follow Chris and ClickUp
Instagram: @Cunningham
LinkedIn: Chris ClickUp
Twitter/X: @ChrisClickUp
Email: chris@clickup.com
––
For access to the exclusive Uploading community, apply at castmagic.io (link in show notes).
💡 Speaker bios
Chris Cunningham is a seasoned entrepreneur and one of the original four founders of ClickUp. His journey into the world of startups began in Charlotte, North Carolina, where he and his close-knit team launched an agency that quickly found success. Fueled by their early achievements and a drive to tackle more ambitious projects, Chris and his crew set out to develop a new social media app called Memory. The inspiration for Memory came from a desire to improve upon Snapchat; while Snapchat erased users’ memories after just seven seconds, Chris’s team wanted to create a platform where moments could be preserved and revisited.
Memory gained traction, proving the team’s knack for identifying gaps in the market and developing innovative solutions. Building on the lessons learned from their previous ventures, Chris and his co-founders eventually turned their attention toward an even greater challenge: reinventing productivity and workspace tools. This vision led to the creation of ClickUp, a platform that has since transformed how teams collaborate and manage work. From agency beginnings to cutting-edge SaaS, Chris’s story is a testament to bold thinking, adaptability, and relentless pursuit of bigger opportunities.
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