The Path to 200 Million Impressions: Chris Cunningham’s Secrets to ClickUp’s B2B Success | S2 Ep. 151
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Ranger, for the ones who get it done. Hey everyone, welcome back to Founder's Story. Today we have Chris Cunningham. And Chris, by the way, you were my first intro.

that I ever ordered from somebody. I've been wanting to get Intro, which is a great app. You advertise like you are now on Intro, and I suggest to anyone, check out Intro. If you don't know what I'm talking about, make sure you look up Chris Cunningham. But we're going to dive in, though, because it was the best 15 minutes that I've spent with somebody in a long time. But you are one of the four people

original founding members of ClickUp, which has become like a juggernaut powerhouse. You're also a sought-after speaker at different conferences around the world. And your goal is to get 200 million organic impressions. But what you do that I don't think I hear a lot of is you're focused on social media with B2B companies and specifically B2B SaaS. Because most of the time, it's about a product, B2C, and it's TikTok shop.

But I think a lot of our listeners, viewers, myself too, we want to know what's the secret sauce to really building social media content when you're B2B? Yeah. Happy to be here, Daniel. This is a shout out to Intro. You were my first Intro call too. I just set it up. I did one just before this. So I'm having a lot of fun with that.

I'll go ahead. I'll start off by giving away the secrets, Hoss. I think the biggest thing that companies are not doing in B2B is they're just, well, one, they're just following what they think they're supposed to do, right? They're listening to what everyone's told them. Everyone's like, hey, let's post on the holidays. Let's use a lot of hashtags.

let's put our brand first and foremost. And everyone's just thinking too much about selling, but no one wants to be sold to in their own social media. So that's the biggest problem. The biggest thing you have to shift and you have to have a big mindset shift is away from just doing what everyone thinks you should do away from just talking about your brand and into making content people love. So the first rule I have for you is the rule of three. If it doesn't do one of these three, you're not going to post it. If it doesn't, number one,

if it doesn't make them feel something, right? Like your content's gotta make them feel something. And I choose laughter, I choose comedy, but it doesn't have to be that. You can make them learn something. That's really rule number two. Rule number two is you gotta teach them and you gotta make them learn something from you. I think that's another really big part. And then the last rule is to really be clear and concise in your messaging. So make sure that whatever you're saying, you're just being clear and concise. You don't need to over fluff it. For example, when ClickUp launched ClickUp Chat,

I could have went all into the product and all the features it had, but instead, all I did was I built this campaign. I went to Salesforce during their biggest conference of the year, which they own Slack, and I let everyone know that, hey, we're cutting to Slack. We now work with ClickUp. ClickUp has chat. The goal is just to let people know we have chat. They will come to your site, and they will learn, but you need to have a clear and concise message. Don't try to put so many things in one video or so many things in one campaign. Have one goal. Make it clear and concise.

And then back to the make them feel something. Again, your content should, as they scroll, they should stop and be either curious or they should be like, oh, this is going to be funny. It should peak interest. And if it doesn't, they're just going to scroll and you're just going to lose to others. So I think that's the beginning of the secret sauce, but I can dive deeper as we go. Yeah, no, I appreciate that. Let's dive into that because I think people are like, okay, how do I make entertaining content when maybe what I'm doing isn't?

is considered kind of boring, right? Like there's nothing like earth shattering, revolutionary. I'm not a comedian myself. How do I create entertaining content? So first off, you got to start testing something, right? So if entertaining is the route you choose, and I'm not telling you have to choose entertaining. You could choose informative. You could choose something different. But if you do choose entertaining, you're going to start testing. You're going to see what your audience likes.

And trust me, I get it. My software is, you know, project management is not the most entertaining thing from a bird's eye view, right? It's logging tasks, it's keeping up with work, it's being productive. But I do think there's a cool message in there. And that is that work is cool. You know, getting your work done is awesome. Doing it in a great way that you're proud of is cool. But there's also another route you can take. And that's where I just make fun of work, right? Because I still just want people, my goal of this content is to be top of funnel. My goal is for you to know about ClickUp because there's,

As big as we are, there's still people who haven't heard of us. There's still people who might not have tried us out for project management. So my goal in this top of funnel content is just for them to know about us, to be like, oh, I really like ClickUp's content. Because then when it comes time, they will still check us out. They'll still be curious. Do they have a good product? I understand what they do now. So that's why you have to have middle of funnel and bottom of funnel as well. So the goal is to cast a wide net at the top.

And just get people hearing about you. Like, okay, what is ClickUp? You know, start asking questions. Like this company makes me laugh every day, once a week on my social media. I'm going to learn what they do, right? Eventually you're going to click the landing page and I have my bio and I have designed that for you to learn what we do to be able to set a demo. So the secret sauce is really not to oversell at the top of the funnel when you're creating the content. It's just do something they like. And to do that, you need to start testing. And that's, this is, I guess, the second part of the secret sauce is how you test.

So you need to, in my opinion, you got to hire a creator. Unless you have someone really good who works at your company, you need to hire a Daniel. You need to hire someone to be their host of a podcast or someone to create the funny videos like we're doing. You have to find that one person that needs to be their sole job.

because it is a very important job. It's only getting more and more competitive. And if you try to just take someone, your social media manager to do an hour a day of trying to create content, they're going to lose to the people like us who treat it like an operation to the people like us who treat it like a TV show. So until you start treating your content as such and thinking about it, you know,

like having writer's rooms, fully putting in time, you won't win. And then secondly, you need to start testing. So as you create this content, you need to test and then you analyze. So start creating your videos for a week and then take all those videos, put them in a Google doc or Google sheet. If you're in like 1994, if you're in the new age, you can use ClickUp or whatever else. I don't care what you use, but find some type of table, take those different video links and then take the video views you got and say, okay, this one did great, highlight it green.

This one did okay. Highlight a yellow. This one did not do good. I'm going to highlight it red. And then the reds, you're going to say, okay, we need to switch that up or not do it again. Yellows, maybe just change the hook. Maybe change a few things about it and try to make it into a green. And then your greens, you remake it. It's an A. It won, right? It did great. Remake it. Do it in a different version. People already like it. You see they like the format. Don't reinvent the wheel. Make another piece of content like that and do that week after week after week. And your numbers will go up because you're learning your audience. Amazing.

I'm glad you bring up hiring somebody who can do it because I think we're all like, oh, I know the business. So I should be the forefront. I should be the face. I've seen a few companies recently that hired interns

And the interns were in the social media account. And now the intern is like head of social media. Because somebody who's in their early 20s most likely really knows how to manage social media compared to when they're in their 40s or 50s, right? If you wanted to do something more informative than entertaining, do you have any advice for people that...

that are like, I just really want to inform people, but obviously I don't want it to be boring. - That's the most easier route. And I think there's a few ways you can do it. You can do what we're doing right now. You can use StreamYard, you can use Riverside, you can start interviewing good people. And the key there is to really, really work on the questions, right? Like any good podcast. If you look at any diary of a CEO, any of these podcasts that do really well, it's because of the research they do, right? They really research the guests. They ask them questions no one else is asking them.

And then they have their audience in mind. Like they know what they want to learn. It's a huge key. So I think you can go the podcast route, but you really need to do your research. Again, whatever you're doing in content, the main goal I'm going to keep preaching to you is don't half-ass it. You know, really dive in. Make it a real thing. Like make it a real, not just something where you show up, I'll have a few questions, like fully dive in, do the research and things like that. Now, let's say you don't want to do a podcast.

Okay, amazing. There are creators who make informative content. Maybe turn your brand into news for what's going on for the week. Like give weekly updates, give daily updates, but find a creator who can do it in a funny, cool format. Find a different format. Maybe it's man on the street. Maybe you're going on the street at these conferences or just going through New York, wherever, big cities, and just interviewing people and keeping your brand alive.

at the forefront of the pulse of what's going on. People are stuck at home a lot. So when they pull out this phone, they want to either learn what's going on, they want to see what's happening in the news, or they want to laugh, right? So you need to position yourself as one of the few. And there's other things you can do. You can do kind of game show type, something fun where people can come hang out. That's more long form and a little more challenging, but there's tons of options you can do. But the first thing you got to do before you do any of this

is know your ICP, right? Who is your ideal customer profile? Who do you want to like this content? Because if you don't know that part, you don't even know why you're creating content. So I highly recommend doing calls like you and I are doing now and ask these people, like ask the people you're trying to sell to, what do you watch? What do you enjoy? What do you learn from? You know, like, what is it? Is it a certain podcast? Is it a certain, you know, they might be like, hey, there's this creator,

X, Y, Z, who just breaks down, you know, project managers and how they work. There's something like that. You never know what it's going to be, but there's always something that you can go down to. So maybe, maybe the beauty is niching down. There's a friend of mine named Shiv. Shiv made this content on humans. He has a podcast on humans of multifamily and it's taking off. And the reason being is I think no one's done that. You know, a lot of people love real estate.

and are trying to learn multifamily and things like that. But now there's a direct place. They can do it. And so he just got there first and he's doing a great job. So I think you really can niche down if, again, you know your ICP and he knew his ICP. How do you look at production value? I feel like in the beginning, it was like low production. And then everyone was like, okay, now we need high production. Mr. Beast.

big stuff. And then I feel like it's kind of going back to maybe like a lower production, more raw video. How do you feel about that? You're on it. You know, look, a lot of our most viral videos are shot off the iPhone, right? And I'm not saying every video, sometimes we still shoot with the camera and we're doing like a music video or something where we feel, you know, having that higher cinematic touch will help. We'll use a camera. We own Sony's, you know, we can do that. But I agree with you. I think you've nailed the trend. The trend now is

content got so over overly done that people are tired of it. And they want, they kind of just want more. People just want to feel that they know you. People just want to feel that they're inside of your life and,

So I think now it is going back to that raw content. And some people are even mixing the two. But again, I think anyone who's overthinking content, shoot it with the phone. It's all good. I'll still use a camera for some stuff, for certain videos I'm trying to make. But a lot of it gets outperformed by my stuff I just shoot on the phone. So yeah, don't overthink it. Set the phone up, turn it around, and shoot. When I think about platforms, the obvious go-to B2B is LinkedIn. However, you and I were talking about TikTok.

and the power of TikTok and what that can do. So what are you seeing when it comes to platforms? Because I think this is always a big thing, like, where do I go? Where do I put my content? Do I put it everywhere? Do I make specific for each platform? What are you seeing when it comes to platforms? Look, naturally, the answer should be you should be omnipresent, right? You should be on as many platforms as possible. That gives you the most chance. But

But what I also argue back is choose the platforms you're good at because if you try to make the most best and most perfect content for every single platform, you'll lose. You only have so much time. Even me today, I'm making content for two platforms, and that's TikTok and LinkedIn. And everyone used to laugh at me at TikTok. They're not doing that now. But everyone used to laugh at me for TikTok. But I'll tell you my reason for it. One, there's no platform where I can get more reach. There's just not.

TikTok can just get a major reach with a new account. Instagram Reels sometimes can pop off, but it's just not like TikTok. Secondly, there's nothing else where I can learn if a video is good or not if I need to change it. TikTok, I get very fast results. I know pretty quickly if the video is going to do well or if it's not. If I need to change it, re-edit it,

it, etc. So the goal for me is I'm creating content for TikTok, but I'm also posting on Instagram Reels. I'm also posting on YouTube Shorts. I'm also posting on Facebook Reels. And some of those videos I even post on LinkedIn. I might just make a few different tweaks for each platform so it's still kind of new for that platform. But I'm creating it mostly for

And then I create my other content for LinkedIn being my carousels, being my more written content, because the beauty is when I post it on LinkedIn, I can still post a carousel on Instagram, right? I can still post, you can post a carousel on TikTok now. But, you know, I really kind of create for those two platforms and then repurpose. But it's not really a repurposing as I still change it around. And it's funny, one video that does really well on TikTok,

I still post it to others, but even if it doesn't, a lot of times I still put it on Instagram Reels because I've had some videos that got 20K on TikTok views and might get two or three million on Instagram Reels. So my goal is I create my short form content and I disperse it everywhere I think it makes sense. Some I know are going to do well on LinkedIn. That's okay. The ones that are a little more businessy,

I'll put those on LinkedIn. I mean, I had just a video last week, get 6,000 likes on LinkedIn, right? It also did well on TikTok and Instagram. So there is some indicators there usually where I can also tell. But LinkedIn is prioritizing videos, especially those vertical videos. So

It's a fun time right now. But again, the key for me is video content. And it's winning. Everything is proving it. If you had to figure out short-form content, now is the time. So let's break down that 6,000 liked LinkedIn post. What do you think that post was different compared to the other posts that didn't get that much engagement? Yeah, on this one, one, it has a character. And that's what I'm learning. Most of your videos that do well have some type of character. HR goes hard is...

two HR guys that people know or people can relate to, right? Two guys who really take their job seriously and pull back nostalgia music that you love. But this video wasn't an HR Guys Hard. The one that was last week was one of our new channels called Almost Quitting Time. Check it out. And it's some amazing actors out of LA. But this one, what it did was it had this character who was an IT guy. And his name is Vic. And Vic is like this very confident, like not like your actual IT guy. Like he's, as he's fixing, he's fixing this girl's computer. And he's,

He's kind of annoyed by her. It has a pretty serious problem and he's fixing it. And basically she starts hitting on him. And he has a lisp and he's like, in your dreams, sweetie. And he's this overly confident IT guy that you've never seen before. And he's almost like,

you know, she wants him, you know, it's kind of like it builds this tension and she like puts her hand. She's like, why do you tease me like this? Why do you, why do you do this to me? And he's like, sweetheart, one, your router is not connected. So then maybe there'll be a better connection. You know, he has like these funny one liners and people, I think, and I think it also related with a job title. So people in it were like, Oh my God, I love this guy. So the, the points we hit were that we, we, we humanized the video. We made a character Vic that everyone can love, right? We made this it guy cool and,

Two, we had him in a funny situation where this girl is hitting on him and she wants him, but she's attractive. He doesn't want her. And it's just kind of funny that it builds this tension. It's a different scene than what you'd expect. It's something different than what you're seeing on B2B content. No one else is kind of building that. And it has that kind of The Office feel. It's actually shot in higher quality. But it feels like you're watching a scene from The Office. And it's kind of hard to put away. It's hard to skip. It's hard not to laugh. It's very funny. I suggest checking out. It's maybe like a week old.

But yeah, I think we really nailed a lot of big things. That's why it worked on TikTok. It worked on Instagram and it really worked on LinkedIn. That's unique. So a dream of mine is I want to be an actor. And I think you've given me the confidence and inspiration. I am going to become my own actor. It's not a love. No, thank you for breaking down. Let's just circle back to you, though. My final question here.

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During building ClickUp and any of the other things that you've built as well, what has been a challenging moment that you've overcome and how did you? I think one of the biggest challenging moments for me in my career was ClickUp wasn't big at the beginning. No one knew who we were. No one cared about who we were. And I think it was tough because we had failed just before this. We created an app called Memory.

that was a Snapchat competitor. Snapchat erased all your best memories in seven seconds. So we created an app that didn't do that. And we thought we were going to be a big hit until Snapchat came out with Snapchat memories. And that really hit us, you know, and that, that, that was a big hit. So I think coming back from that failure and coming at it again, you know, cause it's, it, there's nothing tougher than telling everyone you love, everyone that respects you like, Hey, I'm building something that's going to be big and then failing, failing publicly. But coming back from that, you know, I think is what we needed to really put our energy in and,

go all in in Palo Alto, all four of us living in a house and build ClickUp. So, you know, we really locked in and we did that from there. I think the hardest part for me was really staying true and staying strong as I was making call after call after call. I was our first sales rep and doing everything I could to close a deal when no one wanted us, no one cared about us at the beginning. But as I kept fighting and, you know, the product kept getting a little better and eventually I got that first close. And then, you know, I remember I would go for 50 no's back then. That's what I would do. I would go for 50 no's

And after that first close, I never really got to 50 again. I started closing another one and then another one and then started to become more and more common and ClickUp started growing really fast. So the biggest challenge for me was going into a space that was very crowded, that was very big and being a small group of people and fighting to make our name there. And I mean, it's really cool now to see we employ so many people that we save a lot of people's time. And I think we're just getting started. I think it's still a lot more of a battle to do. Now I'm just fighting a different game rather than fighting sales. Now I'm fighting for brand and for content.

Wow. I mean, we all got to start somewhere. And I think that's always the fear, right? Like you're starting off with zero and there's always more giants in the industry and you have to compete against them. And it seemed many times impossible.

but I like the perseverance in your mission. And you said you were going to make ClickUp something and you've made it something maybe even bigger than what you could have imagined. But Chris, this has been a great conversation. I think I have the tools to go start making my videos and I'm going to send you the results, by the way.

Dude, please. I'll help you along the way. I would love to help. I need to start shooting more myself. I've been a little, I've been so focused on ClickUp. So let's do this together. I'll keep you accountable. All right. I like that. There we go. All right. Then I'm going to come over. We can do some, some, some funny, entertaining videos. If you want to get in touch with you, they want to find out more information. How can they do so? So for me, I'm Chris at ClickUp.com always. I'm never changing my email. For an Instagram, I'm just at Cunningham and my last name and TikTok.com.

And then on LinkedIn or Twitter, I'm just Chris ClickUp. So please hit me up. I'm very responsive in all my social media. I'm posting all the time. I'm really focusing on LinkedIn and I'm about to start picking it up on TikTok and Instagram as well. So thanks so much, man. I really enjoyed the combo. Yeah. Thanks so much for joining us today on Founders Story. Thanks, Chris.

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