How To Win in B2B Social in 2026 with Chris Cunningham, Founding Member at ClickUp

Speaker A: This episode is brought to you by Six Sense. Their conference breakthrough is hitting Las Vegas in November. Three days of workshops, two really big parties, and one new Agentix certification to earn. Visit sixsense.com breakthrough to register. ClickUp's comedy page just might pass their main brand account in followers. And that was the bet all along. Not a happy accident. Welcome to another flashback Friday, pulling an episode out of the vault that's still just as relevant today. This week we were revisiting my conversation with Chris Cunningham, founding member of ClickUp, who built one of the best social content machines and B2B from scratch and turned it into a whole ecosystem of, uh, spinoff pages, employee creators, and viral comedy sketches. We get into his exact content formula for knowing what to create next, why he's betting big on employee generated content, and the marketing hill he will die on that. Obsessing over attribution is what kills most brands before they ever get good at this. If you ever been told B2B can not be fun, this episode is proof it can be. Let's get into it. Welcome to the Marketing

Speaker B: Millennials, the no BS Marketing podcast. I'm Daniel Murray and join me for unfiltered convers with the brains behind marketing's coolest companies. The one request I tell our guests stories or it didn't happen. Get ready to turn the up.

Speaker C: What is up? Uh, we are back with another episode of the Market Millennials podcast.

Speaker B: Today I have the Chris Cunningham, founding member of ClickUp. And you might see ClickUp everywhere. Chris is a part of that. He runs all the social. He does a lot of other things I don't know about at ClickUp because he's a man of many talents. But the social is what ClickUp is like, known for. They crushing it, uh, on all channels. And we're going to dive in today. So, Chris, welcome to the pot.

Speaker C: 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, to do this finally.

Speaker B: Let's just get into it. 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, um, we'll get into how, what's working, what's not.

Speaker C: Yeah. So they almost go hand in hand. Content's always been a big part of my life, uh, in the early days and how I got a part of ClickUp is really just meeting Zeb in college. So, Zeb, for those 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. And so we ended up taking on our first venture, which was managing a rapper. And in doing that, we realized that social was gonna be a big part of us getting this rapper 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, uh, rapper we were managing, we were opening up for, 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. And then, you know, as I graduated before Zeb, um, I got into the, uh, the working world. I was one of the youngest managers at a company called Cvent. And when doing so, Zeb continued learning what we, 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. Should I see this happening? So we started building like 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. I've always believed in him. And, you know, 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. He said, look, I don't want to just be somebody who grows social. Like, I want us to be people who change the world. And that's when we had a bigger plan. So 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. Everything you, your best memories were gone, right? We thought that was a fatal flaw. So we created this app called Memory and it looked hot. We thought, we're gonna be the next Zuckerberg. From there, Snapchat, Bill, 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 be in Sana, some would be in Trello, some would be in, uh, Jira. And no one seemed to love their tool. And that's when we decided to go all in on clickups. 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 but so much content for us. Right. I 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 anything 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.

Speaker B: I actually think I remember the social agency days because I used to live, uh, in San Diego, and I used to see you guys marketing jobs, and I was. And then you switched to this app, and I was like, wait, weren't they a social media agency?

Speaker C: Yeah.

Speaker B: So we

Speaker C: were, we were. We. We pivoted. So a lot of people know that we. It was a pivot.

Speaker B: Um, let's go into it. So you, 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. Um, let's go behind the strategy of how you think about social and how brands should think about social, especially in the B2B space.

Speaker C: 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. Um, I've always felt like what everyone says is not always right. Right. 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. 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. People don't Remember this? But, like five, six years ago, influencer marketing was not really a thing. And 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, uh, you know, everyone does it and everyone saw it. And so now the next thing that I saw is that I believed that everyone was going to have a creator because the space is getting tighter. Like, you can't just, you can go still pay for super bowl commercials like we did, but it's not going to have a consistent impact, right? Might have one big impact for you and people talk about you and put you on a different stage, but. 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. We'll let you test. And this is why, uh, 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. You capitalize, right? And that's exactly what I did. I found this guy Luke, very talented, had already built a TikTok for, 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, um, I, you know, chased him for a while, hired him, and at the beginning, 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 was like, hey, do anything we can to keep doing this. And 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.

Speaker B: So let's go over the motion. I mean, huh? You saw creators were a thing and you needed a face for the A brand, which I think B2B are still behind that. But yeah, creators internally are a great move. So what is, what's the, the process of making a video with creators? Um, how, what is like Monday, Tuesday, Wednesday, Thursday, Friday, look for you when coming up with ideation, video posting, um, restrategizing.

Speaker C: 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. 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 work 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. And 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 day chill out, look at what we did, make sure we analyze and say what, what's going to post on what day and then plan 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, uh, hey, let's wake up one day, write some scripts and shoot. It's not like that. You got to build a machine. You need an operation. And that's what we've really done well here.

Speaker B: And what is, 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 your, your B2B brand, but also, um, you trying to get some sort of message in the market. Um, so what, what are those guardrails look like?

Speaker C: 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? You can sneak it in every now and again. But if you're just doing that, you just 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, uh, 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 on 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. It's a lot of, uh. Like, even when we have the scripts written, when they're shooting, sometimes some of our most like viral videos just came from. We call letting them play. So sometimes the actor's like, yo, we got this really cool idea. 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

Speaker B: 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 writers room and how many times you bring in, let's say, a comedian versus, uh, someone to just refresh the ideas? Because I think that's a 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 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. So what does that look like?

Speaker C: So well said, man. And I think that's the biggest mistake of most marketing teams, right? Is that, hey, we're the best, we're the best, we're the best. But no, it's. You need to have other people come in. You need a fresh set of eyes. You need a fresh perspective. So I would say of every. We do four writers 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. You'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, you know, from you. And they bring things that you never would have thought of, and they really hit. So I would say about 50% of time, 30 to 50% of the time, I'm bringing in someone else. I want some fresh ideas.

Speaker B: I know. So, for example, let's go down one road of, like, a series. So you had that, like, the 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. And I give it. If one video works, come up with the next part of the series, and next part of the series, next. 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? Uh,

Speaker C: so the main way that I serialize content, the way I think about 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? Like, 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. That's a mistake. When you 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 is 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. Now, the other thing we did is then we said, okay, what if we did different music genres? So sometimes it was the 90s for millennials, but, like, that's what we think about, right? But there's also the 70s and the 80s of music. So then we pulled music from different, uh, genres, and that did really well too. So that allowed me to really get the M 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. People will get the content, will get exhausted. So you need is to look for B's. 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 Cs 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 F and then D. D is my favorite, favorite part about content, Daniel. And it's, 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. So what I do is I have a formula. So each week we're going to do around, you know, 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 Bs, maybe like 2 or 3 Bs because they still have a pretty good chance of, of hitting their four, maybe four, because they're proven Cs. We just do like once whenever a trend comes up. And then Ds, 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, but 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.

Speaker B: Yeah, and I feel like a lot of the D like, uh, not a lot, but like a portion. Maybe 10% of the Ds become A's, and you know, they just weren't. If you didn't do the Ds, they wouldn't have been A's at the beginning.

Speaker C: There you go. And then if you never. And if, if not your A's will get 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. Cause I have other things that work now.

Speaker B: 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. 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 lot of the A's are things like people have done funny skits about

Speaker C: sure

Speaker B: things in 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 bees. They are things that are working for that industry. That has nothing to do with me or that greater. Um, but if I just switch it into me, that's like kind of a lower lift because it's already on social. Um, the A seem to be like things that have like worked on like TV or like some other realm or even something

Speaker C: just worked for you, you know,

Speaker B: 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.

Speaker C: Yeah, they love

Speaker B: it. 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.

Speaker C: 100%. 100%. That's the formula. And if anyone else follows it, it will work.

Speaker B: Um, so A, B, C, D. So that you have this. You have this science broken down. What is, um, what have you figured out as the science of a good video? What is a breakdown of a good video? What, in your perspective, what makes a great video on social?

Speaker C: Yeah, what makes a great video for me is. Well, number one, if it's relatable, if it's shareable, if it's contagious, right? So 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? And 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 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. Like, it makes it. Is it worth my time or not? They see the headline like, pov, you know, 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 that'll hit too. Fourth is pacing. You know, is there a part where it gets boring? Does it. Does it keep your attention throughout? And then the last is. We, uh, call it like a button. Is there something that just makes it end so well that maybe 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. Just it 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 them want to hit share, that makes them want to hit the group chat. Right? I think Mark 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 why I want 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. Like, that's, that's what makes a great video to me. And B2B.

Speaker B: Yeah, I think I said this. Actually, I wrote a little bit post about this. But I think if you. The number one thing I think about with any social is, um, is like, optimize, especially for, like, these social platforms. Instagram, for example, um, if you can get into the DMs or in the stories or to Slack channel that metric, I always, I look at that, that share metric more than it. And if I get more, I try to beat the likes with the

Speaker C: 100

Speaker B: shares. That's my, like, goal is like,

Speaker C: there you go.

Speaker B: Then that's how, 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 you probably are looking at is you could tell video drop off really well now on oh yeah platform. So if a hook's good and then they drop off, this might be something in the middle and the hook's good and like it's trailing and then there's a deep drop of the end something bad. You could tell where in your video you are missing which is so useful. Um,

Speaker C: crazy

Speaker B: at this point. Yeah.

Speaker C: 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.

Speaker B: And I love on Instagram now that you use good trial to non. So you're not your non. 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. Which is a great feature they have uh,

Speaker C: smartest feature they've ever added. It's been huge for us. We won't post a video without trying trials first to know.

Speaker B: I know you you 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 are working for you and going into 2026 and what are you you're thinking about?

Speaker C: There's a lot of new things I'm trying and you know, one is these like creator led like new pages. So you basically get one create. I've seen lovable base 44 a lot of these pages doing it. Uh, even cluly you get like 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 like teaching something. So let's say it's like dev tips with Chris. And in these dev tips I'm giving out dev tips but 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 and from someone that's not your brand, not on the brand account, it has a higher way to reach. So I call those like creator led pages. Secondly, EGC. I'm um, all in on EGC employee generated content. Uh, I have like 15 of my employees creating content now and 5 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. And let's say you're ah, 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, um, one of our best sales solutions 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 uh, 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 and 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, uh, 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 the 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. If 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 got to be there somehow. Foreign

Speaker A: let's talk more about breakthrough. The three day B2B industry conference taking over Vegas November 2nd to the 5th. 50 plus sessions split by role, marketing, sales Rev ops, execs and more. You can even earn a certification to help you win the agentic GTM era on site. Plus two big parties and rooms full of people obsessed with your exact problem. Visit 6sense.com breakthrough to save your spot.

Speaker B: I think the one just going back to the first thing because I think people probably going to miss m 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, part of clickups like Media Hub, uh, that are doing tetra ClickUp maybe Comedy for ClickUp. Um, and they're just generating views on the side but they all directionally part of the ClickUp 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, you're growing it on the side. Is that, is that what's going on? Is you creating multiple accounts on multiple platforms?

Speaker C: You nailed it. So what we're doing is I have ClickUp page, right? But I have ClickUp Comedy. I have uh, 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 with ClickUp and ClickUp Comedy or a joint post with 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. I think people love the comedy page page so much and that's how I've been. It's proven to me that we were right to bet on comedy because this ClickUp comedy page has like 340,000 followers, whereas I think ClickUp has 400k. Right. So it, it might, and it's growing faster. It might surpass, but now I can still use ClickUp as that one anchor to still joint posts with ClickUp Comedy joint post with ClickUp Memes. And so you can still go on our page and see a mix of all the different pages we have. But it's better to have the separate page and keep that separate audience because not everyone wants to follow ClickUp but they might want to follow Tips with ClickUp or ClickUp Memes. That's fine, but it's building A big ecosystem that all still goes back to one place, ClickUp and are still very well branded.

Speaker B: And I think, uh, I think this all stemmed from the early signal was okay when you first started. I'm going to get a bunch of creators. Um, I'm going to use attention from their audience. Now we've grown our audience. Like can we be the internal

Speaker C: exactors

Speaker B: where, where media pages are some of the creators. Not technic creators, but sub pages. And then employees are sub creators too because they're part of the click of universe. Um, they're just different characters in the. In the universe.

Speaker C: Exactly. With and get. We're engaged with all of them. So on Instagram you can joint post. On LinkedIn you can like and repost. Right. So we're just making sure we repost everyone's stuff. So ClickUp is the main base. We're helping grow these other big audiences as well, which is great. And then at the same time sometimes I lean on other creators. So I might go like, I might say hey Daniel, with Mark and Millennials. Can we do a joint post? Can we engage us together? I get other creators like uh, Joe Fendi, Fried Chicken, Corporate Bro. Right. We've worked with, with you know, major creators like this and then we tap into their audience, we joint post with them and then. And our audience also sees them. So it's kind of a, uh, I'm glad that we can always be a win win and help new audiences find them too.

Speaker B: Yeah, I think that, I mean join posts are one of the best things that happened on, on Instagram because I've done a couple of the marketing millennials where like me and corporate humor did a joint post and we, we like react our post just because we did it. We just shared similar ideas, but we both collabed on the ideas and they just took off. So I think finding ways to collab with other audience relatively your size or if you want someone bigger, obviously pay to play with.

Speaker C: It's a good play. It's. Anytime you can do eyeballs is a good play, but you got to have good content to make sure you still get the followers and the ROI on it.

Speaker B: Yeah, that's. I think let's dig into that a lot because I think some of people are doing this the Instagram play. Some of them are like trying to do the Instagram break, trying to do the TikTok play, trying to get, do all these plays. But I think the biggest problem is it comes down to not doing what the platform wants or not doing what actually works. And is shareable, um, which we talked about before. And I think a lot of times people come to me and say, why is my LinkedIn not working or my Instagram not working? It always comes down to looking at their content and being like, would you share this content? Would you do that? So I think, how do you teach people internally to start selling what you sold at ClickUp? I know that the testing, the idea is one thing, but if you could tell someone to start small today just to get their feet wet in doing this, what would you tell them? That

Speaker C: this is exactly what I would tell them to do. I would tell them to go start looking at content they enjoy, start looking at content that they feels like matches their brand. Right? For us at ClickUp, we like to laugh. That's why I thought this would make sense. And we thought the business world was a fun thing to make fun of. That would still come back to us. So what I would challenge any person out there who wants to create a content strategy, their company, but is having a hard time. I would say first look at the ethos of your brand and choose one of these three ways where you're going to make people laugh. We're going to teach them something. We're going to add value, right? So what is that? Is it creating a news station for your, like a news page for your space? Is it creating uh, you know, uh, like a course or creating like a free masterclass to be better at this job for your icp or is it making your ICP laugh? Is it one of those three? Figure it out, then start testing. You can still test all three if you're not sure which one it's going to be. But then you just got to start testing. And the way you're going to do that is the most low cost way you can is you're going to scroll through social media. You're going to scroll for some time and you're going to find a couple creators you really like. But they're not big yet. They've got 15,000 followers, 22,000 followers, 6,000 followers, but they've had at least one to two videos that have hit meaning like a 200k or a million. So they, they've learned the algorithm, they've had success, but, but they're not perfect at it yet. And you're going to reach out to them and say, hey, look, I know many companies are not reaching out to you for brand deals yet. I see something in you. I think you can do something great, let's work out a deal. I Don't have so much budget for this because I need to prove to the higher ups that this will work because it's exactly what I did. And you say, okay, let's work out. Maybe it's 1500amonth, maybe it's 2200amonth and you're going to make 15, 20 videos for me. So we can at least post three, four days a week and get some some traction and see some success. And you could do with one or maybe two creators, have them both kind of, you know, battle it out, but get some and then start posting these videos and start looking for signals. So when something does bad, mark it as red. When somebody does decent market as yellow, maybe try it again with a new edit and change it up. And when something is green, you congrats, you found an a20k, 30k, 50k video. Now recreate those as many times as you can. And then from there, once you have a video that hits a couple times, you find some consistency with it. You find a formula. And then you go to your board and say, hey, I got 10 million impressions for us last month. What is that worth to you? And they say, oh, 10 million impressions. You know, we pay X amount for that. Okay, why don't you give me that? I'm going to get it with organic and then we can bring our cac payback down with our ads. We can have more of a brand and I can get better and better at it, make this cheaper and cheaper and that's what they'll do. So they'll say, okay, now let's give you 4K and see if this creator creates 40 videos. How will we do? That's what you do. You start small, you find a creator, you find a formula, then you find a creator at a pretty good cost. But you bet on them and say, but look, once we make it big, I will pay you more because you should as they start adding more value and you try to lock that creator in full time. Because other people, if you don't see their value, others will. And trust me, many people have tried to steal and take my creators. That's why I have to properly incentivize them and take care of them.

Speaker B: I think what you also said, which I think the part I was going to ask you about is how to sell it and how to sell the revenue side or what you're doing. I think one where you said impressions, we pay for a CPM of M X amount on Facebook and Google. If we do that on, on social, how much is that? Worth to you. And then, oh, this is trickling down to this metric. To this metric. I think selling it like that because what people don't get on like Facebook and they are guaranteed impressions. But guaranteed impressions doesn't mean guaranteed eyeballs. It means guaranteed that it's going to show up in someone's feed. And doesn't mean they enjoyed it. Exactly.

Speaker C: Doesn't mean they cared about it.

Speaker B: So if you could create content that does that and then reverse engineer, what they care about is, okay, we get 10 million impressions. That's how much. This is how much it costs in social. Look, when we get 10 million impressions, CAC, payback goes down. Um, um, cost to acquire a customer goes down. People know about ClickUp more. Um, all these metrics start going in the right direction. That's how you sell it. I think that's perfect. I wanted to ask you too. How are you thinking about AI content using AI and social in 2026?

Speaker C: You know, I don't probably have the hottest take on here. I'm still in the camp of I love AI, use AI all the time. I don't think you should fully automate your content with AI. I'm not the believer in that. I don't think it writes the best content. I don't use it for my scripts. I might use it for ideas here and there. But, you know, everyone's saying, oh, AI is going to make every video okay. I don't see it yet because I still think right now people want creators. They want like genuine human. If anything I've seen that requested more like they still, they'd rather see a lot of AI videos don't perform right because people, they, they just, they know it's AI and they want to keep scrolling. However, I do think there's a lot of good things you can do with AI. I've created an AI meme pa. I think that's pretty good. I think you can still make some funny quick memes, images, videos without putting too much work into it and have some success with some thought. Uh, so I do believe in those. I, uh, do believe in still creating. Like I posted an AI video the other day for ClickUp. I still believe in like making AI videos, but I don't believe making it your whole strategy. And I don't believe handing over the keys to make AI do everything right. AI write the scripts, AI make the video. I'm not saying it'll never get there, but for now I just don't think that's the case. And I think if anything People are screaming for more real. Like, they'd almost rather you just walk out and talk on your phone than seeing some AI video or some highly produced video. Because right now they're just. They're. They're not in office with people as much anymore. They're craving something real and hearing, like, real conversation. So when you look on TikTok, when you look at Instagram, on more of the talking head videos, it's more just someone being real and just sharing real thoughts that AI can never pull out together. Just thoughts straight from the brain. So that's a lot of beauty in it. So my advice to everyone is still make sure you use AI. Uh, like streamline things where you can automate, where you can get ideas from AI, where you can build out plans and, you know, use it to track your data where you can. But I would not lean on it completely. I would not have it write all your captions. Exactly. Maybe use it and start it that way, but I just don't think it's there yet. But make sure you're still playing with it. Make sure you're still using every day. Because you also don't want to be that person caught behind. If AI does start really working in content, you need to make sure you understand it.

Speaker B: Yeah, I think that's the best way to put it right now. Understand why it works, how it works, how to do it. But I do. I'm in the camp also is there's some human things that AI can't replicate. And this humor that hasn't been told yet, that only humans could do this. Scripts that I feel AI doesn't have taste yet, I would say. Yeah, so if you feed it taste, it might give you taste. Like, hey, here are all my videos. What is the common thing that's going on here? Maybe they come up with something that is trending.

Speaker C: There you

Speaker B: go. Videos. But you are, uh, you're the input, not the. You're. You don't make yourself the output of the content. You're the input. And it's trying to analyze what you're doing, not what, asking it how to make a viral video.

Speaker C: Exactly. That's a good way of saying it.

Speaker B: I want to ask you a question that I ask everybody in this podcast is what is a marketing hill you would die on?

Speaker C: A marketing hill that I would die on is that most companies die in marketing or fail in marketing because they get too, too caught up on, like, attribution. They get too caught up on seeing immediate results. You always lose to companies like us who don't do that in marketing because it takes time to see some of these results. And it's not to like make marketers lazy or anything. They should still be held accountable. They should still definitely be bringing in revenue. But those who are too afraid to try anything, those who are just going to follow the same playbook, those who will just do something that brings them immediate roi, like Facebook ads, they'll only get. But so far, because I told you, it took me three or four months to really start even seeing great results from this plan. It took me maybe seven to nine months before we had a big deal close and say, hey, we found you because of your TikTok. Right. But it still happened and there's still many more that it's happening that we probably don't even know about. But it took, you know, almost a year before we started becoming the brand that everyone's talking about. Oh, ClickUp is the, the gold standard for, for content. Only got there by, by breaking this so so called rule of like, we need, you know, X amount of leads and X amount of eyeballs from every piece of video you make. If luckily my CEO Gaurav was cool and, and let me run with this. Luckily our CEO Zeb understood, um, and saw the vision because now they love that every conference we go to, oh, I love your brand. Oh, I love your marketing. You know, like that that is priceless and that, that puts you in a different category. That's a moat. That means people are always going to know about you. Right. But you will never get to the levels we have, the views that we get without being prepared to maybe not have ROI for a couple months. Exactly. And not be able to see it. That's the beauty of marketing and it's also the toughest part of marketing because I also still understand those people who are very numbers oriented. I do, I'm very numbers oriented myself. But you got to take risk. Like everything in life, like every big founder, you know, you got to take some risk and that's the risk of marketing you're going to have to take. So the hill that I will die on is you can't just overly track attribution immediately last click all that. You got to just take the risk, keep going, keep iterating and believe that it will come together. That's the only way you're going to get there.

Speaker B: And you said it, you said at the beginning, I think we just reiterated that you don't. You started off with a very small budget and the budget kept growing as you started proving results, and that's why it's working. But you had this test budget to, to do an experiment and then show that. And I'm in agreement on that. I think even in the age of AI, this is even more important, this brand stuff, because the way you get talked about at AI is you get showed up in a lot of places because of your brand. And if you don't have a brand, um, paid social is not going to get you AI views because nobody cares about your brand on page. But if you, if you, um, are doing fun things, shareable things, seen as the best content, people are going to talk about you more and more and that's what the LLMs, uh, are going to see. And you're going to get fed and people are going to. Your brand is going to pop up more and more in the age of AI as well. So lastly, where could people find you? ClickUp. All that good stuff.

Speaker C: Yeah, ClickUp's pretty easy to find just at ClickUp. You can find any of the other pages. ClickUp Comedy. If you haven't seen any of our videos, I'm biased, but you should check it out. I think we're definitely doing something different and we're doing something fun. Uh, for me, I'm just at Cunningham, my last name, as you see down here on Instagram and just Chris ClickUp on Twitter and LinkedIn. I'll, um, I'm, I'm another fair millennial, always creating content. Uh, very easy to get in touch with chris@ClickUp.com if you have any questions, if I can ever help. Uh, I love helping this. I love supporting the community. I love marketing and I want to see everyone win. I know how tough it is to win. That's why I'm glad we have people like you, like me, who are just out handing out the secrets as much as we can. So we, the marketing world can be better in B2B.

Speaker B: Yeah. And I think that's, that's the key of winning is, is adding something to someone's day or adding someone to some, someone's job or adding something that can make someone better. Uh, so I think go out today and with your brand, do something to make someone better, their job. Smile, do something that someone will do and that your marketing will work. If you do, if you think along that

Speaker C: 100, if you're being unselfish and you're just wanting to go share and give, it will win every single time. And yeah, Daniel, we're both in Miami so we need to hang in person soon. I've been traveling so much, man. I know you just had a new kid, so my father will definitely hang soon.

Speaker B: Well, uh, talk soon.

Speaker C: All right, man.

Speaker B: Thanks so much for listening. Keep tuning in to hear more great

Speaker D: insights from the coolest marketers from around the world. If you haven't already, make sure to subscribe. Subscribe and follow the Marketing Millennials podcast on Apple Podcasts, Spotify, YouTube, or wherever you get your podcast. And if you like what you hear, I would greatly appreciate you giving us a five star rating. It helps bring more marketers into our community.