Ultimate Guide to Social Media Marketing for B2B in 2026

[0:00]Social media is not an afterthought for B2B companies anymore. It can't be, it's 2026. Your buyers are on their phones, they're scrolling Instagram, they're watching TikTok, they're on LinkedIn, which is more like a social media platform than ever before. But most B2B companies are still treating social like a place to post, say, blog links from the company page or posts about the new webinar that you're doing. But there's another way. Chris Cunningham is a great example of this. He is one of the founding members at ClickUp. He's been there almost a decade and built their entire social operation from scratch. He told me something that I think every B2B marketer needs to hear. Number one, the problem is just talking about your product. That's what 99% of people do and it's the wrong thing. When people pull out their phone, they don't want an ad. They don't want to be sold to. They want to laugh and they want to feel something. Chris walked me through exactly how they do this at ClickUp. How they run a weekly writer's room and shoot 12-15 videos every Thursday. How they A/B test every video using Instagram trial reels before it hits the main feed. How they find small creators with a viral hit and try to turn them into full-time writers for ClickUp. How they manage 35 accounts across every platform and how this strategy has driven real pipeline and results. We talk about how to measure this, how to think about this, and he gives a couple of great examples. Then the conversation shifted into AI and content creation and I ask Chris about where he thinks AI is going with creators and social media and content. And he thinks that actually doubling down on real human creativity might be the biggest competitive advantage in B2B right now. This episode is jam-packed, it's all about B2B social media. Enjoy my conversation with Chris Cunningham. So, Chris Cunningham, uh, early founding, founding member of the marketing team at ClickUp. You've been there forever now for, you know, uh, 40 dog years in tech, tech years, or whatever. Right? What is it? Has it been a decade? Almost. It's been right shy of a decade. In about four months, it's been a decade, two months actually, two months now. Can I just, in a world where like most people I talk to, myself included, I'm jumping around to new company every two years, uh, what's kept you at ClickUp for almost a decade? Uh, the founding team, man. I've, these are my best friends. You know, I've been through, this wasn't the first company we started together. We've been through three different ventures together. We've had ups, we've had downs. And I gotta see this through. You know, like, sure, I've had opportunities to leave, especially with things popping and doing well. Uh, but, but I love this crew. I love this team and I, I gotta see this through and, you know, who knows what happens to me in the future, but it's, it's the team. Okay. And then, how do you, you've carved out, you, you've, you've kind of like played a bunch of different roles in the company as, as it's grown. Um, my view, and I'm not super close to ClickUp or what you're doing, so I'm not gonna try to explain for you, but, fuck it. It's my podcast. So, like, closely I see you as like B2B, the, the reason, uh, I was drawn to have you on the pod is because, I think it might've been in a, in a conversation with Tim from Ahrefs or I've just, I've been on your content for a while. Yeah. And you talk about my favorite subject, which is, uh, B2B marketing and social media and you seem to have a point of view on how it works, why it works and so it's been, we've been like two ships passing in the night for a long time, but I want to have you on to talk about that. Am I true in kind of reading that, like, you've, you've carved out this interesting role in social and, and content in the company? I think I made up my own role from being honest. So look, yeah, at the beginning I was our, our VP of sales, right? I was the first sales rep, closed our first $10 million ARR. And, uh, as we grew, I knew that wasn't my passion, right? I was just doing it because I was the only one of the original four who could talk on the phone and, and handle sales. And I had sales experience, but I had always had a love for, for social media for marketing. And I, I think the, that's one of the reasons why I've also stayed because who else would let me try this crazy stuff? I've got actors twerking, you know, in videos, right? Like, what other company can I go to that they let me do that? Now, maybe since I've proven it, yes, but like, only at ClickUp could I try and have this free rein and so that's another reason why I'm still here. Okay, so we're gonna talk about B2B social today. The goal is to leave you with some ideas, just ways to think about things, get you unstuck, give you some inspiration, that, that would be a successful, uh, episode here. So first, can you explain you have this way of writing and you've written it before. I can't perfectly articulate it, so I'm gonna ask you as a question, but how do you articulate the value of B2B social and what's the mistake that most companies are making when it comes to thinking about social as part of the marketing strategy? The first mistake is so easy is that they're, they're treating social media as a place to give more ads, right? And when people pull out their phone, they don't want an ad. They don't want to be sold to. They want to laugh and they want to feel something, right? They either want to learn, they want to add, have some value added to them, or they want to laugh. That's really all it is, or feel some type of emotion. Right? They have some people who might watch prank videos. Some people who might watch videos to learn more about Claude and get better at that. And you know, some who just want to make fun of the business world, right? And that's what I attacked. So, number one, the problem is just talking about your product. That's what 99% of people do and it's the wrong thing. The second is they don't give anything enough time. Right? Like, they don't understand that it might take six months to see if something's working in marketing. And the problem is, that's why CMOs are, you know, that's what, that's why they should be in Exit Five and things like that. They are the most let go or the most attacked, in my opinion, at a company because they don't get as much time to let something win. But for anything in marketing to win, you have to give it time and sometimes it's hard to prove. And that's the, that's the challenge we face every single day as marketers. Okay, so, the big thing that's shifted in our personal lives is that the, for us, the majority of the shopping, buying, consuming that we do is now not only through our phones, but through some form of entertainment, whether, you know, it's Instagram, YouTube, podcasts, TikTok, Netflix. I mean, I'm watching something on the couch the other day with my kids on Disney Plus and there's like a Salesforce ad, you know, like CPG. All this stuff is, all this stuff is everywhere now. And I think what, what I hear you say is like, we want to build a strategy, we want to have an actual point of view on how to be successful on social media and not just treat it as another like distribution channel. Like, oh, we got a blog post, so post about it on LinkedIn or like, we won this award, so post about it on LinkedIn. You, can you, can you explain the like, if we peel everything away, where did, where does someone start? If I'm listening to this, you're gonna give us some good examples and stuff, but how do I peel this all the way back and figure out like, what, it's almost like you need an angle, like what's our angle for social gonna be and do you pick an angle, do you pick the channels? Where do we start? You got it. First off, you, you gotta follow the rule of three, right? So, like, what I do now is I will say no. I still get those requests, like, hey, we have an event here, we need to post that. Well, I'm like, well, one percent of our audience is gonna care about that, right? So if it doesn't do one of the, one of the three, right? So if it doesn't make them feel something, if it doesn't add value and doesn't teach, I'm not hitting post, right? And there's another rule that I have, so before we post, if it, I need to ask what the hook is. I need to ask, why would someone even watch this? Like, why would they care? And I need to follow the pacing, right? Is the pacing there? Like, is it quick and is there a payoff? Is there a reason to watch at the end? So, these are the quick little rules I have. I make sure before even create a post. But now, let's take a step back. Before you even do that, I think the thing is the big, the big thing that you will study is to say, hey, be omnipresent. And I do believe that. You should be posting on every platform, but I don't believe you should be creating for every platform. So for us at ClickUp, I'm creating for two platforms. And one is, you know, can be TikTok or Instagram Reels, they're kind of the same to me, but short form, and the second is LinkedIn. Right? So I'm creating for those two. And all I'm doing is, I'm creating funny, I, I lean into business humor. So I'm creating funny business humor. And then on LinkedIn, I'm writing about thought leadership. And that's, that's the two things. That's it. And then what I'll do is, my Instagram Reels, I put on trial Reels first. One of the biggest gifts I can give you, Dave, is someone does care about short forms. You need to be using Instagram trial Reels. Why? Because think about it. We'll say I have one video, but I do three different edits. That takes my editor maybe an extra four minutes max, right? Now, I have a different text on screen like this. It's where most people read. Now, I have a different hook, a different thing to catch you at the beginning and maybe I have a different format, right? And when I test those in trial Reels, I get, I don't get punished, it doesn't go to my followers. One video will do better than the others, and sometimes they'll do significantly better. So much so that I have a video that would've only gotten 60k if I posted what I thought was better and it goes to like 10 or 20 million. It's a major difference. So, even if you have a great idea that you love, man, this video is, I love it. Press post, it, it's like a standard operating procedure to have three variations of it. Every single time, no matter what, and you'd be shocked how many times the one you think is the best is not the best. Yeah. No matter what, no matter what you should always A/B test if you can and you can today in social media. And does it, is, does it even matter even if I'm, uh, I have a like our, our Exit Five company account, I don't know, we have like maybe a thousand followers. Is that enough? Should I still run trial Reels? Still worth the time. Still worth the time. Every single time. And it's so easy. I'll show you, I'll show you, I'll send you my PlayBook after on how to do it. Your team can implement it in no time. Like, everyone thinks that ClickUp has this big social media team. It's me, some actors that I hire and they're just, but they're not in, you know, and then it's a social media manager. That's it. And my social media manager just knows how to run the trial Reels really well. So, so the for everybody listening. So like, the reason for having Chris on was, I think this is probably the, the thing that I see the most is, and I, I'm guilty of this time and time again where like, We don't really have a lane, but I'm kind of posting content of all different types and all different kinds and I got it on YouTube and I got it on LinkedIn and everything's kind of doing okay. I think it's probably the fact that you honed in on like, we're only going to be on these two channels, so, so, you know, let's use TikTok and Instagram interchangeably and then LinkedIn. And you're not just like making random videos. You're making random videos that all serve this purpose of, like, it's in this category of funny business humor. And what I want to make sure you also know is that I'm, I'm posting on 35 accounts every day now, right? So it's not just Click, I have ClickUp on all the platforms, right? Then I have ClickUp Comedy, I have ClickUp on the street. And so ClickUp is more of my product. That's where I'm helping people. That's where I'm making, that's where I'm doing more like teaching ClickUp or here's three tips to be more productive, et cetera. Then I have my ClickUp Comedy because the comedy, I used to do both and I realized that some people want to watch the comedy, some people want to watch ClickUp personal, so I've made these different pages. But yes, so I'm leaning into the business humor. But when I tell you that I'm only creating for two platforms, I'm still posting across all of them. True. So when I make the one video for ClickUp, but you must have gotten it. You probably didn't have all those pages out of the gate. I'm betting that you had, like, your posting funny things that kind of popped off on the main ClickUp channel and you're like, oh, we could carve this out and do its own page, right? And I realized that the audience was getting confused and it was limiting how far I could grow. So, funny enough, ClickUp Comedy, ClickUp has been around for years before ClickUp Comedy. ClickUp Comedy has more followers than ClickUp. Right? But that's just because people love comedy the most. It's a bigger ceiling. And it's also kind of like, that could be anything. That could be a comedian channel, like ClickUp doesn't, you know, go to your head that that's some type of software that someone's going to try to sell me, you know, it's like, Exactly. Like if it was like Salesforce Comedy, it kind of hits differently. It does. So, it is, but you know what it's funny? Because there's, there's definitely some people who follow that page and don't know what we do, but that's fine. Because we're running AI to see who's following who and if I, like, I found out that the COO of McDonald's. The COO of McDonald's follows ClickUp Comedy, right? What do you think I did? Of course, I got my actors to make a video, DM him from the page and set up a call. Because now now I've turned this into a sales motion. And mind you that, for anyone out here who's doubting and thinking, oh, there's no way you can make Did he, did he respond to that message?