The Playbook Behind ClickUp’s $4B Content Engine

Hey guys, it's your host Blaine here. And today we've got some great news. We're launching a brand new private community for uploading and it's all about building your personal brand the right way. The community will feature access to some of the world's best content creators, some of who you've heard on uploading, and more to come. 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. So if you want to scale your content, boost focus, stay consistent, grow your personal brand and connect with other top creators, make sure to apply@castmagic IO Uploading community. We'll drop the link in the show notes and hope to see you there. Welcome to today's episode or workshop of uploading.

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.