How To Win in B2B Social in 2026 with Chris Cunningham, Founding Member at ClickUp | Ep. 378

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0:48Get ready to turn the up. what is up we are back with another episode of the marketing millennials podcast today i have the chris cunningham founding member of click up and you might see click up everywhere chris is a part of that he runs all the social he does a lot of other things i don't know about it click up because he's just a man of many talents but the social is what click up is like known for they're crushing it on all channels and we're gonna dive in today so chris welcome to the pot Happy to be here, man. I've been watching it for a long time and friends with you for a while. So I think that the time has come for us to do this finally.

1:26Let's just get into like, first, let's get into the story of how you even got involved in ClickUp and how you got involved in social and then we'll get into what's working, what's not. Yeah. So they almost go hand in hand. Content's always been a big part of my life. In the early days and how I got a part of ClickUp is really just meeting Zeb in college. So Zeb, for those of you who don't know, CEO, founder, real genius of ClickUp, who is the builder, the architect, everything behind what we're doing. And me and him met in college and we were just bored. You know, we really didn't think that everything we were learning we were going to use and we wanted to do so our own things.

2:02And so we ended up taking on our first venture, which was managing a wrapper. And in doing that, we realized that social was going to be a big part of us getting this wrapper attention. So we did. We started really learning social media, learning how to grow, learning how to get attention. and that worked really well. It allowed us to get a song on the radio, allowed us to get a tour. So our little rapper we were managing, we were opening up for Wiz Khalifa, Mac Miller, even if it was like the first smallest opening act, we were doing that and we were on the tour and that was awesome. That was cool.

2:30And then, you know, as I graduated before Zeb, I got into the working world. I was one of the youngest managers at a company called Sevent. And when doing so, Zeb continued learning what we did from the rapper and created like an agency. And I would help him on the side while still at Cvent. And there's some things that I learned while being there, like, hey, corporations are really going to need to start getting big on social soon. I see this happening. So we started building an agency to help companies with social. And that was our first project together. I left Cvent to go work with him because I believe in Zeb.

2:59I've always believed in him. And we grew the agency pretty big. And then one day Zeb has a near-death experience. Like Lily almost died. And he comes back from that and he said, look, I don't want to just be somebody who grows social. I want us to be people who change the world. That's when we had a bigger plan. The first one was to create a new social media app. At the time, Snapchat was the biggest app of its time. It would erase all your memories in seven seconds. Your best memories were gone. We thought that was a fatal flaw. We created this app called Memory. It looked hot. We thought we were going to be the next Zuckerberg.

3:32From there, Snapchat built Snapchat memories. We lost all our money and we had to pivot. and that's what a lot of people know about ClickUp. We really had pivoted. Our first mission was something else. But we had built this tool internally because we hated working with other teams and some people would be in Sauna, some would be in Trello, some would be in Jira and no one seemed to love their tool. And that's when we decided to go all in on ClickUp. So that's how I got in and I've always been obsessed with content. And even at the earliest of ClickUp, I wasn't doing with so much content for us, right?

3:59I was doing everything else I could. I was our first sales rep. I was doing customer service. I was writing blogs, trying to run ads, just any marketing I can do. And as we grew, that's when I got to create this perfect role for me, which is, you know, taking content, being ahead of the content game and making sure we have a brand people know about us, people talk about us. I actually think I remember the social agency days because I used to live in San Diego and I used to see you guys marketing jobs. And then you switched to this app and I was like, wait, weren't they a social media agency? Yeah.

4:33We were. We were. We pivoted. So a lot of people know that it was a pivot. Let's go into it. So you've generated some crazy numbers. You're in the B2B space where people say social doesn't work. Social, you can't use TikTok. You can't use video. You can't have fun. Let's go behind the strategy of how you think about social and how brands should think about social, especially in the B2B space. The best way I can say that I think about it is almost how I've done everything in my life. Like when I look at school, you know, everyone told me, Hey, get one job, move your way up. I've always felt like what everyone says is not always right.

5:10Right. And that might be arrogant. That might be like the wrong thing to say, but it's honestly always how I felt. I think sometimes when everyone is saying something, it's not right. It doesn't mean it's right. And it doesn't mean it's wrong always, but I've always liked to go against the grain. And so when I really fully took over all the content and everything at ClickUp, I was like, I want, I always have everyone telling me what to do. right? But I see what I believe. And I believe that a lot of things that they say we can't do in B2B are going to be big. The first example was influencer marketing.

5:38People don't remember this, but like five, six years ago, influencer marketing was not really a thing in B2B, but it wasn't B2C. And my number one rule is if something works in B2C, it's probably going to work in B2B just a little bit later. And that's why I really went hard on influencers early on. And now we see how successful that's been. And everyone does it and everyone saw it. And so now the next thing I saw was that I believed that everyone was going to have a creator because the space is getting tighter. You can go still pay for Super Bowl commercials like we did, but it's not going to have a consistent impact.

6:09It might have one big impact for you and people talk about you and put you on a different stage. But if you want eyeballs every day, that's something new. And that's where you have to win in the creator economy. And so that's why I wanted to invest in the creator economy. And I went to our board and I asked them, hey, let me get one creator that just works for us all the time is creating videos. They're like, okay, look, we're not going to hire them full-time to start, but we'll let you test. And this is why I challenge any good marketer. I'm sure, Daniel, you've interviewed tons of people who say this, but in marketing, you need to test with a low budget first, look for some signal, and if you see it, then you go all in.

6:40You capitalize, right? And that's exactly what I did. I found this guy, Luke, very talented, had already built a TikTok for one big company called Ad World, and I saw he knew how to do it in a B2B way. So I hired him, and I chased him for a while, hired him. And at the beginning, it was just me and him working and we were making the videos ourselves. And from there, we didn't have much success the first month. Then the second month we started having a few videos hit a million. And by the third, we had videos hitting 10, you know, 10, 15 million. And once we had millions of views aboard, it was like, Hey, we'll do anything we can to keep doing this.

7:08And that's when I hired Luke full-time and then hired a second actor full-time and this became a whole motion that we do. So let's go over the motions. I mean, you saw creators were a thing and you needed a face for the brand, which I think B2B are still behind that. But yeah, creators internally are a great move. So what's the process of making a video with creators? What does like Monday, Tuesday, Wednesday, Thursday, Friday look for you when coming up with ideation, video, posting, re-strategizing? I'll give you the whole play. we run it like this on monday we've all come together and we look at everything we did last week okay this is what worked this is what didn't uh and let's act on that tuesday we all come this is today later today i'm going to go in about two hours i'm going to pitch all my ideas to the team and everyone comes together with some ideas and they say okay i saw this work or this worked for us previously we all pitch about three to four ideas and at the end of that we vote and we say okay these are the best ideas these are what we're going to shoot on wednesday we fine-tune them we perfect the scripts, perfect the hook, perfect who's going to act as what role.

8:18And then Thursdays we shoot and we shoot from 8am to 6pm. We get as many videos as we can, sometimes five, sometimes four, but as many as we can. And then from there, now we have our videos for the week. Now we have everything. And then Fridays is kind of our day to chill out, look at what we did, make sure we analyze and say what's going to post on what day and then plan it out again. So you have really two planning days on Monday and Friday, planning and analyzing days. And then the action days are Tuesday, Wednesday, Thursday. That's what most people need to realize is if you really want to win in content, this isn't just a, hey, let's wake up one day, write some scripts and shoot.

8:49It's not like that. You got to build a machine. You need an operation. And that's what we've really done well here. And what does the ideation look like? What is the criteria that people have to meet when ideation? I feel like there are some guardrails because you're a B2B brand, but also you're trying to get some sort of message in the market. So what are those guardrails? look like? Yeah. Look at the beginning, you know, they were like, Hey, we need the brand in every video. And I kept saying like, you can't do that. Right. Like think of TV. When you watch TV, it's like 85 % TV, 15 % commercials, right?

9:22You can sneak it in every now and again, but if you're just doing that, you're just gonna be putting that bucket or people are going to scroll. So some of the guardrails we have is obviously I'm not going to go too far and go too crazy. I don't want legal in my ear. I don't want to be having any trademark issues. I don't want to get sued. I don't want to have people hate our brand. So we're very careful in speaking about, you know, the topics like politics and things like that. We don't touch any of that. Uh, but we do, but we, other than that, we don't have too many guardrails. It's a lot of having fun.

9:48It's a lot of, uh, like even when we have the scripts written when they're shooting, sometimes some of our, some of our most about like viral videos just came from what we call letting them play. So sometimes the actors are like, yo, we got this really cool idea. And we're like, you know what, go run with it, go crush that. And we allow them to do it. And I think that's been a big play. Going into that too. I know we talked about this, but you, you also have like a writer's room type thing where you also bring in guests and new ideas and cool different things so what does that look like in the writer's room and how many times you bring in let's say a comedian versus someone to just refresh the ideas because i think that's a lot problem with a lot of marketing teams as well as you get into this box where you can't come up with ideas or you stuck with ideas or you can't come up with new ideas and you just need another pair of eyes to just come in and say, hey, let's just do this or this or this.

10:43So what does that look like? As marketers, we're all trying to answer the same question. Which investments are actually driving revenue? And too often, the honest answer is an educated guess. CallRail replaces that guesswork with proof. With the help of AI, you can connect every lead to the exact campaign that drove it. Analyze your conversations and capture leads around the clock. That's why over 220 ,000 businesses use CallRail to market smarter. Stop estimating impact and start proving it. Try CallRail for free at callrail.com slash prove it. So well said, man. And I think that's the biggest mistake of most marketing teams, right?

11:28Say, hey, we're the best, we're the best, we're the best. But no, you need to have other people come and you need a fresh set of eyes, you need a fresh perspective. So I would say of every, we do four writer's rooms a month, right? I would say one to two of them, we bring in another writer. I might just bring in another employee at ClickUp who has a cool perspective or a cool idea, but I'll go out and I'll find like another comedian, another content creator, and I'll just pay them and say, come to this, come to this with like three ideas, but also hear us out and help us punch up our ideas. And it's insanely valuable because sometimes you get stuck in a box.

11:56You've created the same type of content. You get kind of stuck on what you think is working, But then you bring in someone else who has a new idea, new perspectives, new life, different jobs from you. And they bring things that you never would have thought of and they really hit. So I would say about 50 % of the time, 30 % to 50 % of the time, I'm bringing in someone else. I want some fresh ideas. I know. So for example, let's go down one road of a series. So you had that HR parody song series that you came up. I think like something that people miss with content, especially in B2B is like serializing the content.

12:31And I give it if one video works, come up with the next part of the series and next part of the series. Don't just come up with one idea and then just post that idea and it doesn't work. So how do you think about like serialization of content, making sure that people see that? So the main way that I serialize content, the main way I think about it is I use the ABCD formula and the ABCD formula works like this. When you do have something that works, you've struck gold. That's why you create content, right? So when you have that, that goal that you found, we call that an A. And what that means is that's like the first time we did the HR dancing, right?

13:02Like first time we did that, we could have just been done with it, right? So we had a great video. Let's keep creating new. That's a mistake. When you've struck gold, you need to capitalize on gold. You need to recreate it, but don't do the same thing again. Find a new way to do it. So I'll give you an example. The first two was HR goes hard, right? Then I tried finance goes hard. Then I tried, uh, you know, sales goes hard. So I just made the same guys. They were HR guys or sales guys. I just kept bringing different departments because that reached a different audience. So then we did it. So now we're doing the same proven formula, but with a different audience.

13:33Now, the other thing we did is then we said, okay, what if we did different music genres? So sometimes it was the nineties for millennials, but like, cause that's what we think about, right? But there's also the seventies and the eighties of music. And then we pulled music from different genres and that did really well too. So that allowed me to really get the most juice out of the squeeze. And that's why I think most people mess up is they don't capitalize when they found that hit. But here's the other way you can mess up. If you're just creating A's and you just create that same piece of content, eventually you will run out of juice.

14:01People will get, the content will get exhausted. So you need is to look for B's and that's where you look for other things that are working for other people and you find a way to do it your way. And then C's are trends. Anytime there's a trend, jump on a trend. If you can and you can add value to the trend, you should do it. It's quick, easy views. Don't do only trends. That's how you fail. And then D. D is my favorite, favorite part about content, Daniel. And it's experiment with the unconventional. Try something new. Do something knowing else is done. Go be unhinged. That's another thing people love, especially on TikTok and Reels.

14:29So what I do is I have a formula. So each week we're going to do around six to eight A's because we know they work. It's our highest highest hit probability, right? We have a science behind this. So we hit A's, then we do B's, maybe like two or three B's because they still have a pretty good chance of hitting their four, maybe four, because they're proven. C's, we just do like once whenever a trend comes up. And then D's, we try to do one brand new thing a week and that might get our lower views, but every now and again, you'll strike gold with the D and it becomes an A. So your goal is to keep creating different content that becomes more A's.

14:59But while you're using the A's, being smart enough to notice when they've kind of exhausted and you need a new piece of content to sub in. yeah and i feel like a lot of the d like not a lot but a like a portion maybe 10 percent of the d's become a's and you they just were if you didn't do the d's they wouldn't have been a's at the beginning there you go and then if you never and if if not your a's will get it like people will get tired of your a's like i can only do this dancing hr guy it's still working somehow but eventually it'll slow down but that's cool because i have other things that work now yeah and it's also i feel like some things that you said with what you're talking about is there's a lot of proven models just not on social and not in other industries in other formats and other ways where you could do things that are funny but haven't been brought to your industry so there's like like i think the a a lot of the a's are things like people have done funny skits about sure things on snl but they haven't done it about hr so let's like see if i could do an snl type skit on it about hr like the b's they are things that are working for that industry that has nothing to do with me or that creator um but if i just switch it into me that's like kind of a lower left because it's already on social um the a's seem to be like things that have like worked on like tv or like some other realm or even something just worked for you it you know and then but it has originality to it too because i feel like a lot of them are not exactly i would not say that you're copying any of these things it's more i know that funny improv type skits people like yeah they love like let me just make some type of improv skit that will work for me in a different way in an original way and let's see if it works.

16:53100%. That's the formula. And if anyone else follows it, it will work. So A, B, C, D. So you have this science broken down. What have you figured out is the science of a good video? What is a breakdown of a good video? In your perspective, what makes a great video on social? Yeah. What makes a great video for me is, number one, if it's relatable, if it's shareable, if it's contagious, right? So if it's something I see and I automatically want to hit the share button and send it to someone, that means it's going to be a good video. Two, if there's something really cool you can comment, you might make a great video, but there's not much to say about it, right?

17:32And if that's the case, the need of it is that great a video, it might not go as viral as it could because there's no reason to really comment on it or engage with it. Number three is the one that everyone says, but it's not as big as it used to be as a hook. So your hook and then your headline, like having a really good headline can actually really make the difference of a video. Because that's the first thing people see. It makes it, is it worth my time or not? They see the headline like POV, you just started a new job or something like that. You get the right headline that's relatable or funny enough to make them want to see the end.

17:59That'll hit too. Fourth is pacing. Is there a part where it gets boring? Does it keep your attention throughout? And then the last is we call it like a button. Is there something that just makes it end so well that maybe either you want to watch it again or you just feel pleasant afterwards? right? Like, is there, because sometimes you have a great hook and a great body, but you just don't end it well. It just doesn't end how they want. And then that kind of messes up the video. So I think you need those five things to really be a successful video. And the biggest ones are making sure you, you have something in there that makes someone want to hit share.

18:30That makes someone hit the group chat, right? I think market millennials does a great job of that. You know, like you see, you see that in WhatsApp groups or in slacks all the time. You guys have a cool post, they go share it. And same with ClickUp. Like they're like, oh, this reminds me of, you know, Joe at work, or that's what I'm going to make like a video, making fun of the IT guy, a lot of people probably send it to their IT guy or the IT guy sends it to his IT friends like, hey, this is us. That's what makes a great video to me in B2B. Yeah, I think I said this actually, I wrote a little bit of a post about this, but I think if you, the number one thing I think about with any social is like optimize, especially for like like these social platforms, Instagram, for example, if you can get into the DMs or in the stories or to a Slack channel, that metric, I look at that share metric more than it.

19:23And if I get more, I try to beat the likes with the shares. That's my goal. If I can get the biggest, then that's how I know this is hitting for an audience and I'm going to keep doing that idea is more people are sharing. The like thing is like just signal. It's not, but share is someone had a deep reaction. And I think one thing social does really good, and I think this is what you probably are looking at, is you could tell video drop off really well now on social platforms. So if a hook's good and then they drop off, this might be something in the middle. If the hook's good and like it's trailing and then there's a deep drop off of the end, something bad.

20:06You could tell where in your video you are missing, which is so useful. Crazy. At this point. Yeah. That's what's so valuable. That's why too many people give up on a video. Like I made a video just the other day that we thought was really going to hit and it didn't. And I was like, you know what? It looks like people dropped off here. We messed up on this. So rather than just giving up on the video, I'm going to go re-edit it. I'm going to post it again because very few people saw it. Right. So never give up on a good concept when you think you can find the problem and fix it too. And I love on Instagram now that you just could trial to non-follower.

20:37So your non-followers don't even see, your followers don't even see what you're doing and then you can flop all you want to non-followers. It doesn't matter. Which is a great feature they have. Smartest feature that ever added. It's been huge for us. We won't post a video without trying trial wheels first. I know we talked about this before you got on, but what are some things you're testing now, trying? What are things you're figuring out that are working for you and going into 2026? And what are you thinking about? There's a lot of new things I'm trying. And one is these creator-led new pages.

21:12So you basically get one creator. I've seen Lovable, Base44, a lot of these pages doing it even clearly. You get one person and they're just creating a video daily. And the video is not really an ad, but kind of an ad. So you're basically teaching somebody. So let's say it's like dev tips with Chris. And in these dev tips, I'm giving out dev tips, but usually in one of them, the tip uses the product of which I'm pushing. And so it's just getting a new audience every time. And you're basically betting on like of the 30 videos they make three or four go viral. Right. But with that, you still get a pretty big audience.

21:44And from someone that's not your brand, not on the brand account, it has a, it has a higher way to reach. So I call those like creator led pages. Secondly, EGC, I'm all in on EGC employee generated content. I have like, 15 of my employees creating content now, and five of which are doing really well. You know, 20K plus followers and the rest are coming. We're getting close to 10. I think it's just a great way to make content, especially on LinkedIn. That's where I care about the most because right now everyone wants to learn. No one has time to go back to school. So the best way to really learn is by being on LinkedIn.

22:17And let's say you're a sales solutions engineer. You're going to learn from another sales solutions engineer at a company you respect, right? So that's why Liam, one of our best sales solutions engineers, I have him creating content. What makes you so good? Why are you so great at your job? Just speak about it. Just talk about it. People want to know. And he does that. And he's getting great engagement now and starting to grow. And that's just one of many examples. But I'm really, really high on EGC. The next thing I'm high on is I'm thinking about the next level. I think that this creator-led brand thing that I have is great.

22:47And the short form is great. But I think there's going to be some long form. I think there's going to be companies making short movies, short films. There's this new thing called Real Short, where it's like minute-long episodes of seasons. I think content is going to evolve and I think that brands need to be on the forefront of it by really treating themselves, not as a full media company, but making sure they have some type of consistent media that they know they can bring in new eyeballs and keep attention, whether it be edutainment, funny like me, or just teaching people something, just making them better at their job.

23:17If you can't do one of those three, you're probably not going to hold their attention when they finish their workday and they pull out their phone and you've got to be there somehow. I think the one, just going back to the first thing, because I think people are probably going to miss a lot of what that actually is. A lot of people only invest in their brand account. So like ClickUp Investing, ClickUp or ClickUp Investing. but you're saying um you're investing in other pages that are adjacent or um or part of click up's like media hub that are doing text for click up maybe comedy for click up um and they're just generating views on the side but they're all directly part of the click up universe but it's not all going in the brand account because you can some things you can't post on your brand account So you have other pages where you're growing it on the side.

24:10Is that what's going on? Is you creating multiple accounts on multiple platforms? You nailed it. So what we're doing is I have ClickUp page, right? But I have ClickUp comedy. I have ClickUp on the street, ClickUp memes, tips with ClickUp, right? I have all these different pages. But the way that you bring it together is the beauty of with Instagram is I can have these different pages, but I can still sometimes joint post it with ClickUp, right? So I can say a joint post of ClickUp and ClickUp comedy or a joint post of ClickUp and ClickUp memes. but then you grow your own page. So the ironic thing is ClickUp comedy might pass ClickUp's main page and followers.