S5E15 – How to leverage Social Media to become a $4B company with Chris Cunningham

Are you wondering on how to leverage social Media to become a $4B company? In this episode of Grow Your B2B SaaS Podcast, host Joran welcomes Chris Cunningham, head of social media at ClickUp, a company that has grown into a $4 billion entity since its launch in January 2017. Chris discusses his transition from VP of Sales to leading ClickUp’s brand and social media strategies, offering valuable insights into how ClickUp leverages social media to generate impressive monthly impressions and build a recognizable brand.

Social Media Strategy and Brand Building

Chris emphasizes the importance of creating unique content that disrupts viewer patterns on social media. By doing so, companies can capture and retain their audience’s attention. Early on, ClickUp focused on crafting humorous and engaging content with limited resources, which helped the brand gain visibility. Building a brand that people talk about has always been a core goal for ClickUp.

Consistency in Achieving Virality

While achieving virality can be challenging, maintaining consistent virality is even harder. ClickUp’s strategy involves setting ambitious goals, such as reaching 200 million monthly impressions. Chris highlights the importance of testing different content types and strategies to see what resonates most with the audience.

Employee and Founder-Led Content

Chris advocates for involving employees and founders in content creation. This approach helps build authenticity and engages diverse audience segments. Sharing progress, setbacks, and behind-the-scenes insights on platforms like LinkedIn can significantly contribute to establishing a strong brand presence.

Platform Experimentation and Engagement

ClickUp has explored various social media platforms over time, initially focusing on Twitter and Instagram before shifting attention to LinkedIn and TikTok. The key to success is staying omnipresent and adaptable, continuously testing new platforms and adjusting strategies based on their performance.

Content Creation Balance

Chris shares how ClickUp strikes a balance between creating humorous content and educational, product-driven content. Their strategy involves a structured content calendar that includes brainstorming, scripting, shooting, and editing. This process helps them consistently produce engaging and informative content.

Successful Social Media Tactics

Leveraging humor and value-driven content has been critical to ClickUp’s success. Humor not only drives engagement but also serves educational purposes, such as humorous training videos. For conversions, content that offers significant value, like detailed guides or problem-solving resources, has proven highly effective.

Challenges and Lessons Learned

Chris recounts challenges such as misjudging the audience at a developer conference and making early hiring mistakes. He stresses the importance of understanding the audience and staying flexible to feedback in order to refine strategies over time.

Future of Social Media and Long-Form Content

The episode concludes with Chris discussing future social media trends, including a shift towards short-form and mid-length content, as well as the potential of emerging platforms. Chris shares his goal of creating content that invites audiences to “hang out”—similar to popular B2C content formats—offering a more engaging, community-oriented experience.

Practical Insights and Takeaways

• Differentiate and Engage: Stand out by creating unique, engaging content. Use humor and educational elements to captivate your audience.
• Build in Public: Be transparent about your journey on platforms like LinkedIn to foster authenticity and deepen connections with your audience.
• Be Platform Agnostic: Don’t limit yourself to one platform. Test and adapt strategies across multiple channels to identify what works best.
• Employee and Influencer Content: Incorporate content from employees and influencers but ensure you maintain control and ownership of your channels.
• Measure and Adjust: Track key metrics, such as impressions and sign-ups, through specific landing pages to gauge the effectiveness of your efforts.
• Learn and Pivot: Embrace failures as learning opportunities. Continuously refine your approach based on audience feedback and performance data.

Conclusion on How to leverage Social Media to become a $4B company

Chris Cunningham offers a wealth of practical advice for SaaS founders and marketers looking to leverage social media effectively. From the importance of standing out with unique content to the value of building in public and employing a structured content creation process, this episode provides actionable insights for anyone seeking to grow their brand and achieve substantial reach on social media.

Key Timecodes

• (1:23) – Chris Cunningham’s Background and ClickUp Overview
• (2:15) – Early Social Media Strategies for ClickUp
• (4:12) – The Story of “Tyler” the CEO
• (5:59) – The AppGator Tool
• (7:13) – Using Social to Identify Competitor Weaknesses
• (9:02) – Humanizing B2B Social Media
• (10:30) – Combining Humor with Educational Content
• (11:15) – Effectiveness of ClickUp’s Content Strategy
• (13:41) – Employee and Founder-led Content
• (15:10) – Building Machines for Content Strategy
• (16:53) – Impact of Funding on Social Media Strategy
• (19:50) – Importance of Being Scrappy
• (20:23) – Tracking Sign-Ups from Social Media
• (22:02) – Deep-Dive Content for Niche Audiences
• (27:47) – Mistakes and Lessons Learned

Transcription

[00:00:00.000] – Chris Cunningham

People are looking for things different on social. The moment it looks like something else they’ve already seen, they’re scrolling and they forgot about it. But the second you shape the pattern and change everything they’re used to, that is when they can start paying attention to your social. I think there’s a couple of things you got to focus on. You need to add value early on. If you don’t make people feel something when they’re scrolling, they’re going to keep scrolling. Even going viral once is not easy. Most B2B brands will never experience it. They won’t go viral because they won’t change their strategy. They don’t keep following the rules. Once you do go viral, it’s a whole other thing to start going viral consistently. That’s a whole different challenge. You need to create employee-led content, founder-led content. Now, you really need to win on LinkedIn. Linkedin is where you need to win. The best way to win on LinkedIn is to build in public. So what I do to build in public is I set this audacious goal. Tell the world, my goal, 200 million impressions. Hold me to it.

[00:00:48.610] – Joran

In today’s episode, we’re going to talk about how to leverage social media to become a $4 billion company. My guest is Chris Cunningham. Chris has been at the start of ClickUp since January 2017. Clickup is the everything work app used by over 2 million teams. They raised in total 435 million with their latest $400 million Series C in 2021, which made them a $4 billion company. Chris started as the VP of Sales took CS with it for a while before moving fully over to brand and social media. He’s now the head of social media. Welcome to the show, Chris.

[00:01:23.810] – Chris Cunningham

Excited to be here, man. You nailed that. It’s a lot happening. I still pinch myself to know that we’re a $4 billion company, but still work to do. We’re not public yet. We’re still fighting giants. There’s still a lot of releases to go.

[00:01:35.140] – Joran

Nice. We’re going to learn a lot more from ClickUp and from the journey from all the questions I’m going to ask. Maybe even a question to begin with, if I remember correctly from a LinkedIn post, you guys want to have 2 million views every month on your social media?

[00:01:48.170] – Chris Cunningham

More than two. We’re going for 200 million. 200 million a month. We’re averaging about 155 right now, and the goal is to get to 200 million impressions every single month.

[00:01:58.090] – Joran

200 million impressions every month. Well, cool. We’re going to break it down for everybody. I guess this is the end goal for people. Now we’re going to talk about how to actually get there. Let’s go to the early days. How did ClickUp leverage social media in the early days when you guys didn’t have the brand you have today?

[00:02:15.150] – Chris Cunningham

In the early days, the way that we took advantage of social was just creating more… We didn’t have all the high-end cameras. We didn’t have that look. But we knew how to make people laugh. I think that still holds true today. What we do is we had a little green screen. We had a very inexpensive camera because back then, I don’t think the phones really would work. We had a camera, it might have been the best. A lot of it would just be me shooting and attempting to be funny. I made raps. The things that you see a lot of people do now, I did it earlier. It’s not that it was super well-executed, but it was that it was different. And that’s where we got a taste. We had one little rap video I did do pretty well. I’m not talking millions like today, but close to 100,000 or something like that. And that was still good for us. That got people noticing us. And when we got really good, I was executing when they did. If If anyone commented, if anyone engaged, follow, we made sure to hit them up. Me being the first sales rep, I would take any lead I could get because no one knew who ClickUp was.

[00:03:10.050] – Chris Cunningham

We’re finding these major companies. When someone was shopping, they were just going to go after the main 10 tools, and that was it. Our goal was just to be seen. That’s how we use social media. We didn’t really have money for ads. We didn’t even really know how to run them, but we didn’t know how to create posts online consistently. Then from that, we would meet people, get in contact. That’s where I would also, since I was on the videos, it was easy for me to reach out because I’m also the guy selling Then I was also the guy helping you with customer service. I was all around and became a face of the brand.

[00:03:35.610] – Joran

I think that’s what a lot of SaaS companies have at the beginning, where it’s the founder who does everything. I guess besides being different and posting, also engaging and actually making sure you follow up on them.

[00:03:47.150] – Chris Cunningham

Huge. What I love about it is even Zab, our CEO, who’s building the product, would also hop in and respond to tickets. That was always really cool for me to see. Honestly, a lot of times I’d have to bring him onto our sales calls as well. He would go camera off use a different name. He would use the name Tyler. That way people didn’t think the CEO, the company was so small that the CEO was the sales solutions engineer. That was a little trick we played for a while until we got bigger and started bringing on those positions.

[00:04:12.640] – Joran

I heard a really good story about that one of your biggest clients who in the end found out that Tyler isn’t actually Tyler.

[00:04:19.410] – Chris Cunningham

That was Randstad. Randstad was the first major company I closed. About a year later, maybe even seven or eight months later, he was speaking to the company. They had him come and he was speaking. Someone just stands up and they’re like, You’re Tyler. He was We were a little bit… We thought they’d be mad, but they really were just impressed that we were able to do that and that we were so small and took so much care. Luckily, it worked out great and they were happy clients. I’ll never get that moment when we got caught for acting like we were a little larger than we were.

[00:04:45.160] – Joran

Love it. And regarding social media at the beginning, I did quite some research for this one. I think you also use it to track negative reviews, to talk certain groups. Can you tell me a bit more how can people leverage social media also by not Nesco was my number one tool.

[00:05:02.560] – Chris Cunningham

If you want to get to 10 mil ARR, if you want to grow to a big company, you need to be scrappy, right? You need to be scouring the internet. There’s two things we did that I would say really helped us stand out. You can find what these are for your company in your industry. Number one, we built a tool called AppGator. Appgator would give me leads anytime someone on social media or on Capterra, Git app, any of these major review platforms, anytime someone gave a bad review or something negative about our competitors, I would get a direct lead, and it would come in through the tool AppGator that we built. Then from there, I could find them on LinkedIn or maybe their email, and I would start reaching out and saying, Hey, look, I understand why you hate Asana. We do, too. That’s why we built this tool, something more flexible. Obviously, I know we’re newer, but give us a shot. You’ve probably already tried all the other tools. We’re shipping every single week. You can talk to me anytime. You can see everything we’re doing. Why not give us a shot? I think that’s what really worked for us early on is that some people would still be skeptical.

[00:05:59.080] – Chris Cunningham

There’s certain people who are always just going to still go with a big company. That’s fine. But there were some people who were really into tech and they saw what we were building. That’s the community and what we built early on. The second thing we did is by being on social media and seeing all these different, watching our competitors and learning from them, that’s where we found out that one of our competitors was actually going under. Productive was going to shut down and they were going to literally just end everyone’s contract with no export. People would have nowhere to go lose all their data, all their work over who knows how long. Our CTO and co founder Alex Jarkowski, was just an absolute genius. He was like, Look, this might take me some days, but I can build that export. And so he stays up and he built that export. Then I was able to come into that Facebook group and say, Hey, look, everyone here at Productive, spread the word. I know you guys thought you’re losing all your work, you’re not. You’re coming over to ClickUp. Here’s the tools how to do it.

[00:06:48.930] – Chris Cunningham

Here’s the export. Do you have any questions? We will be up all day, all night to help anyone move over. We want as many customers as we can. Significantly, we grew a lot after that and had a lot of customers going, so much so that I had to hire more apps, and that’s when I started bringing on customer service reps and all that. Those two scrappy moves, paying attention to social, kept us on the pulse of what’s going on, allowed us cool opportunities to bring on more clients. I think that was a very big stepping stone for ClickUp.

[00:07:13.490] – Joran

Nice. When we go back to posting, how did you guys decide which platform to use and which were most effective for ClickUp?

[00:07:22.140] – Chris Cunningham

We were always testing, but our goal at the beginning was being omnipresent. We were everywhere. Twitter was actually an early one for us. Twitter was working pretty It’s funny, the tables have turned now. I would say Twitter, we get less from, even though it’s still a lot of great founders and stuff, it’s just been a little harder as a brand to go viral. Then Instagram was good for us early on. Then now that has changed. Now our main focus is more TikTok and LinkedIn, mostly LinkedIn. But that, again, we would never… You still have to be trying everything and adjust. Obviously, that changed. But at the beginning, we were just trying everything. We were posting everywhere we could, putting everything out we could, trying to create new types of content. The goal was not really to At the beginning, it’s easy to look at your competitors and just think, Oh, I should do what they’re doing. But that’s really the last thing you should do. You need to find your own way, your own strategy, your own style, because people are looking for things different on social. The moment it looks like something else they’ve already seen, they’re scrolling and they forgot about it.

[00:08:15.060] – Chris Cunningham

But the second you shake the pattern and change everything they’re used to, that is when they can start paying attention to your social. I think there’s a couple of things you got to focus on. You need to add value early on. If you don’t make people feel something when they’re scrolling, they’re going to keep scrolling. For me, now I choose humor. It’s what works really well for my top of funnel. But that doesn’t mean middle of funnel and bottom of funnel, I don’t create more ICP and more product content. But until you test everything, until you validate, you’ll never know. You need to just take 50, 60 days and just say, I’m going to post at least 5 to 6 days a week on these days. I’m going to take data and then I’ll learn. Then from there, that’s how we figured things out and figured out what content people like to see from us.

[00:08:51.830] – Joran

Because a lot of people say, Hey, don’t go to TikTok, don’t go to Instagram because my buyers are not there, but you’re saying the complete opposite. In the end, they’re humans as well. They’re probably going to be on the platforms.

[00:09:02.570] – Chris Cunningham

They’re humans as well. The moment you forget that is the moment you’ll lose on social. I think that’s what most B2B does is they forget that these are humans and they forget that they don’t want to be sold to. The moment they create content, they forget what content they like to watch. There’s no way when you create these contents like, Hey, Merry Christmas, whatever, and it’s just like an image. No one cares. You’re scrolling past it. You didn’t add any value. You didn’t make them feel anything. You didn’t follow any of the rules. The moment you realize that most of the rules that you’ve heard are wrong, I think is the best time that you’ll see brands or having some success on social.

[00:09:34.270] – Joran

Was that a goal, I guess? You mentioned filling up your top of funnel and then, of course, engaging with your ICP. But what was the goal when you started leveraging social media? Was it purely brand awareness?

[00:09:45.460] – Chris Cunningham

The goal has always been to have a brand that people talk about, to do things that people talk about, because we thought back to brands that we pay for. A lot of them were things that we thought they did cool things that we really related to. There might have been two or three other softwares that did the same thing, but we We felt some type of connection to that brand. We like the way they develop. We like the way they talk. We wanted to be that brand. At the beginning, it was definitely more awareness, but it’s always been lead-driven as well. The way you get to lead-driven is not what you think. Again, it’s not just putting out ads on your social. A lot of times I was just teaching people how to use ClickUp. That was what worked really well was just click tips. We mix it in. A couple of videos would be funny, a couple of times it would be click tips. I was the one doing the webinars at the beginning. A lot of times what I would do is I’d have something funny happen at the beginning. The webinar wasn’t really boring.

[00:10:30.100] – Chris Cunningham

I would find little jokes I could put in there. For example, if I was teaching ClickUp, I pulled characters from Silicon Valley and made the personas. That way it could be funny. Like, Oh, Erlik is doing this. I just found more ways to make everything fun. Maybe I might do another training video and make it like a wrap. But those things did really well for us early on. When we noticed that people liked it, they would comment, Hey, this is refreshing. This is a cool way to learn about your brand. Again, it got people talking, Hey, have you seen ClickUp’s video? Their training videos are doing a wrap. Again, it gets people talking. It’s contagious. That’s what you want to do. You want to find other places to do it.

[00:11:03.330] – Joran

I didn’t notice. It’s quite funny. You combine humor with educational videos. You’re teaching them something how to use your product, but in a really funny way to keep them engaged and to keep talking about it.

[00:11:15.420] – Chris Cunningham

Anything to be different, anything to stand out, and anything to still get the mission across. As long as I’m still teaching and doing it a cool way, adding it, who doesn’t enjoy a little humor in there?

[00:11:23.600] – Joran

Yeah, because that was one of my questions, what content were you guys pushing out? It was not just humor, but it was also educational content on how to actually use ClickUp, but then with funny things in between.

[00:11:35.700] – Chris Cunningham

What’s funny is our content hasn’t changed with so much. It’s obviously evolved and we’ve gotten to the style and what’s popular, but we’ve always tried to mix in humor and we’ve always tried to mix in value-based content. I think we strongly believe in that. Think about it, we don’t have time to get back to school. That’s why this value base or this teaching type content is great. We all want to get better at our jobs. We all want to make more money. If I create content that allows people to do that, that’s great. That’s something I’ll engage with and be appreciative of. But at the same time, almost more so, people are not going on social learn. They’re going on social take a break. I want to give them that break in a way that’s still business. It keeps up with business humor. That’s what I think we’ve really nailed and we’re having a lot of fun doing.

[00:12:14.180] – Joran

You’re now aiming for monthly 200 million impressions. You have to go probably viral with a couple of posts you’re going to do out. Were you able to go viral early stage already?

[00:12:24.570] – Chris Cunningham

The early stage, we didn’t go that so viral. We definitely had some things on Twitter, but I wouldn’t call it consistently. The key is consistently viral, and that’s not easy. Even going viral once is not easy. Most B2B brands will never experience it. They won’t go viral because they won’t change their strategy. They’ll keep following the rules. But once you do go viral, it’s a whole other thing to start going viral consistently. That’s a whole different challenge. That’s what our COO, Gora, was really smart about. He didn’t just give us the rule like, Hey, go viral once, and you get this goal. He was like, No, the goal is for three months to consistently hit. At first, it was 20 million impressions, and it was million impressions. Then, of course, he jumps it up to 200 million. I’m sure once I hit 200 million, it’ll be a half a billion. That’s just how the game works in growth marketing. But the goal is to be consistent. It’s one thing to just make one really great video and go viral. Now, we have to be so strategic We have to think of multiple videos that could go viral and then make sure the other ones we’re posting still do pretty solid so we get high numbers.

[00:13:20.250] – Chris Cunningham

It’s a very tough game.

[00:13:22.280] – Joran

Yeah. I guess it’s something probably a lot of companies want to go at the beginning. They want to go viral and maybe that one time and hopefully be Are you lucky? I guess you mentioned already the keys to go consistently going viral, so figure out what is working and what isn’t and try to repeat that all the time. Any other advice you would give here for other founders?

[00:13:41.440] – Chris Cunningham

The other advice I would give for other founders, and what we should have done earlier on is you need to create employee-led content, founder-led content. Now, you really need to win on LinkedIn. Linkedin is where you need to win. The best way to win on LinkedIn is to build in public. What I do to build in public is I set this audacious goal. Tell the world my goal, 200 million impressions Hold me to it. And then every week, I just do an update. Hey, Cunningham, just checking in. This week, I did not do well. You need to have those things. I think some people really appreciate the most when I say, Hey, we had a rough week. We did not hit the goals. This is how I’m going to adjust. This is how I’m getting back on the battlefield. I’m not just going to complain. I’m not just going to not post this week because I didn’t do good. I’m going to share with you. Then the week you do good, you share it. But then you also give them real insight as to how you did it. So I think gatekeeping is the number one way to not do great on social.

[00:14:25.020] – Chris Cunningham

The best way to do great is just be an open book. Give it all away. It took me a second to do that. One, because I have to hire out to be like, Hey, we’re not giving up too much away. But what I realized is there’s a whole difference in execution, and it really is true. The playbooks will get out at some point anyway. No matter what you’re doing, people can watch it, they can see it. You may as well share it, get moving, and do your best at executing better than No one else can. That’s why I think we do a ClickUp. We build machines, we build, we test, we take bets, we execute on those bets. If they work really well, we increase the budget, we increase the effort, and increase the results. If it ever slows down, we move on and pivot. We don’t have any ego. All these are huge secret weapons, and you You better be good at building machines, especially as an early-age founder, because you don’t have as many employees. You don’t have as many things to get going. If you don’t really build that culture early on, it’s not going to happen as you grow later and get more employees.

[00:15:10.980] – Joran

I think what you mentioned is super practical for everybody listening. If you just build in public, you can tell your story or your milestones, anything, basically, and people are really willing to check it out without having to create raps while doing a demo.

[00:15:24.050] – Chris Cunningham

No one’s asking to create raps or crazy comedy like us. Just build, just talk. But you need to have something because it doesn’t It doesn’t matter their position. It doesn’t have to be your VP and your CEO. A sales solutions engineer and one of our other heads of content, Greg, is doing amazing at content. That’s what people are overthinking. There’s definitely someone at another company who can learn from Greg in our company because he’s creating content for a $4 billion company. He has pretty big goals. So someone who’s maybe a $200 million company, maybe they’ve not even raised yet. They can learn from these people. So don’t ever underestimate, Oh, I’m not at this position. Get everyone posting and help them with that. Give them the resources to do it, teach them how to do it, because there is people who are better at posting on every platform and you can learn from them. Take a little course, invest $1,000 and have them take a course, anything like that. But have people get out there and start trying, because again, it’s another at that. Some people are never going to follow a ClickUp. No matter how great of content I post, there’s not going to follow a brand account.

[00:16:14.720] – Chris Cunningham

That’s okay. But a lot of people will follow someone that is in a role at a company they respect if you’re giving values in consistently. That’s why you need to hit from all fronts, not just one.

[00:16:22.790] – Joran

Yeah, because I think that’s how I now see the content from ClickUp as well. I’m not following the company account, but I will see it everywhere now via you or via acquire somebody else.

[00:16:30.990] – Chris Cunningham

That’s cool with me.

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[00:16:53.420] – Joran

You guys raise money, right? In the early days, you were really scrappy, making sure you get a lot of double funnel by free social media. Did something change in your strategy when you guys have more money to spend?

[00:17:05.800] – Chris Cunningham

Sure, definitely. It definitely changes when you have money. Early on, we didn’t just have social media content. We hired a guy who was really good at written content as well, ranking. We’ll see if that game changes now, but that was very valuable for us early on. As for how things change, absolutely. When you have some money, you definitely do want to increase ads because as great as we are, more people can see about us, and especially when you understand your CAC payback and when you’re going to get that money back and what’s worth spending? There’s no reason not to do ads. It’s a rat race to get as many customers as you can and to add value. But I think we start spending more money on, and we’ve always spent the most money on, the product. We’ve always been a product-led company, and I’m so proud to say that we still are and will always be that way. We put more money into the product. We put more money into making things faster, building faster, shipping more features, purchasing companies that can be features, or acqua-hiring amazing engineers. That’s where the majority, I would say, we go.

[00:17:57.200] – Chris Cunningham

Sure, we have a sales team now. We increased that. We didn’t have a sales for a while until we really raised. We were just selling as it is and go with the product. It is great to have a sales team, especially if you want to go enterprise and all that. But I definitely think we spent more on ads. We even started spending a lot on content. At one point, we had an entire video team, and that was awesome. They were creating the best content I’ve ever seen. With that being said, a lot of times that stuff looks great, but on social, it’s not that the high-end stuff doesn’t hit as well. For us to went on social, we had to adjust and figure that out. Now we have more of a… I would say we’re back to that scrappy side of things. We just get some creators, we get a camera, we get an iPhone, we go out and we shoot. But we put more strategic time into it. We have a writer’s room, we have a lot of plans, we work with producers and things. This whole game has definitely came up in budget as well as social.

[00:18:41.960] – Chris Cunningham

But even with having all this funding, nothing changed. I started with a very small budget. I got one creator. I paid him a small number a month and just asked for some videos. Then I went to my COO. I was like, Hey, look, we did 15 million impressions, which is one creator in this small budget. I bet if we brought a second creator in, I could hit more. Then that’s what we did. That’s how the HR guys really came together. Now that the finance guys or the IT guys, they can be all these different guys, but they’re creating content consistently for all kinds of different audiences. It’s a machine, and it doesn’t cost that much. They absolutely crushed it. They do an amazing job, and we’re still lean. We just spend a little time altogether, and we plan things out and then we shoot and then we edit and then we do it again.

[00:19:18.700] – Joran

I think it’s really nice what you mentioned that at one point you had this full video team, the fancy videos, and then you find out it’s not working. So you go back to what is working and then iterate based on that again.

[00:19:31.270] – Chris Cunningham

Exactly. There’s a lot of things you do when you get money, you still test. I’m glad we test it. I still like some of that high-end quality content. You don’t know if you need it consistently all the time. Also being scrappy in the way you spend is important. Just because you have money doesn’t mean you just start spending more. A lot of people think that. I can tell by the invoice There’s a lot of places that come in all the time. No, we’re not one of those companies that just write up. We still negotiate. We’ll always negotiate.

[00:19:50.770] – Joran

Nice. You mentioned already one metric, CAC Payback. What are the other metrics you guys tracked when it came down to social media?

[00:19:58.450] – Chris Cunningham

Cac Payback is definitely a fun one. At At the beginning, it’s impressions. Impressions, just how many eyeballs are you getting? That’s the brand awareness. Now, we’re tracking more signups and who’s actually coming in and who’s buying the tool. We do that by having a custom landing page on our social. You only see this landing page on our social. I know that all traffic that comes there comes from our social. That’s where I can get a feel for the signups we’re getting. At the end of the day, that’s really the next one. We care about sign us. We want more people using the tool.

[00:20:23.370] – Joran

Then based on which landing page they use, you can track them down the funnel to figure out CACPayback.

[00:20:29.670] – Chris Cunningham

If we were a touch point or not, which is great.

[00:20:32.380] – Joran

It’s basically being attributed based on the landing page they would sign up from. If they would click last on your Facebook ad or Facebook post, then they would end up there.

[00:20:41.710] – Chris Cunningham

Sure. To me, as long as we get them in, I don’t mind. I realized at the beginning, people see our content, they might not know what ClickUp does, and it’s cool. I just want them to recognize us. Then I want them to realize we’re project management, and I want them to give us a shot when they’re shopping. That’s what I care about, product, I believe, and how well we’re priced and what all we have. My goal is just to make sure they think of us.

[00:20:59.960] – Joran

Yeah. Maybe I’m asking for a golden nugget here, but what types of content has driven the most engagement, or maybe even better question, most conversions?

[00:21:10.450] – Chris Cunningham

Sure. The funny content always will get the most eyeballs. It’s just what people love, and it’s got a lot of people there. When it comes to actually conversions, that’s a different type of content. That would be more what I would call either ICP or thought leadership content. I’ll give you an example. One of the best posts we’ve done for signups, the best one for me was when ChatGPT first came out. I did this for my personal page. I created a… Most people were doing like, Hey, here’s the 20 best prompts to use ChatGPT. I’m sure you saw this post. What I did was I came in, I was like, Here’s 100 or I think I even gave 200. Here’s 200. This It was just way more value than everyone else was giving. It took time. It was like, Here’s 200 of the best prompts if you’re in business to use for ChatGPT. I put it in a ClickUp Doc. I put it in a way where you have to sign up to get access to the doc. That was our record-breaking sign-up suite because that post went viral. I think it had 10 million views.

[00:22:02.950] – Chris Cunningham

I gained 10,000 followers. It was massive. I think it was the second most viral tweet to Elon at the time. That was great. That’s our most sign up. Secondly, one that anyone else could do. I think that strategy has played out. A lot of people saw that strategy started copying it. The second one I would offer to you is you really dig deep. You go on to Reddit, go on to Cora, and find a problem in your space. Build something visual that solves the problem or teaches the problem. For example, mine was the problem was everyone Everyone got confused with PM versus PM versus PM, project manager, product manager, program manager. There’s way more, really. But I took those three and I was like, Here’s what they do. Here is how they do it. Here are their KPIs. I made this beautiful little doc That one did a lot of signups, gained us a lot of followers, and a lot that were really project managers in the space. You can always create content, but you need to dig deeper. You need to find an actual problem and solve it in a beautiful way, a way that’s very esthetically pleasing to the eye and allows them to quickly maybe 30 40 seconds, learn something, take it in, save it, and keep it moving.

[00:23:03.270] – Joran

I really like the first one where you leverage your own tool to actually get people to get the value from your post. Then you’re not selling anything, but in the end, you are selling something.

[00:23:12.660] – Chris Cunningham

You can’t beat that, right? You can’t beat it. We’re not really selling. It’s free, but you’re going to come on our tool.

[00:23:17.610] – Joran

I ask it already, but I’m going to maybe dive a bit deeper on it. How do you currently balance creating the entertaining/humorous content versus the educational product-driven content?

[00:23:29.670] – Chris Cunningham

Sure. I’m very strict on my calendar. I have my Mondays, which are very geared towards creating the product content, and I have Tuesdays, which is very geared towards the funny content. Both of those days, I’m outlining what happens. On Monday, it’s usually me who thinks the most of the product content. I might go and talk to some of my team, but usually I think of the ICP and that type of content. I just go assign it to designers to build. That’s more visual. Then on Tuesday, I meet with what’s called the Writers Room. In the Writers Room, that’s where me, the actors, and a few others will come in. We We will speak about different video ideas. We’ll pitch them, and at the end, we vote. The best idea is when they get shot, the rest don’t. We blind vote at the end. No ego, no problem. I think it’s really strict to separate the times. If I try to do both on the same day, it’s too much context switching. I really do not believe in context switching. You really need to be strict on your calendar. You need to find a way to separate, Okay, I’m spending 90 minutes here.

[00:24:19.480] – Chris Cunningham

I’m spending 90 minutes here. Then you need to have a process afterwards. It’s not done once we do the writers are, right? Okay, then we have to fully script it and get it out. We do that on Wednesday. I usually shoot on Thursday or Friday. From there, we got to check on Friday, make sure that we know who’s editing what. Then next week, we get them together, and then we’re like, Okay, we’re posting this one, this one, this one. It’s a whole formula that goes out each week. Maybe on Friday, I think of some good designs, and then Monday, I go execute it. I’m in a flow. I know when I’m pushing everything out, I know how many videos per week I can basically put out, I know how much product content I can put out, and I’ve measured how much I think I need of each. I think I need a little more of the funny content top of the funnel and then a little less of the product. It’s almost 65 I would say, geared towards heavier towards the top of funnel fun content.

[00:25:05.550] – Joran

Yeah, and doing it this route, you know exactly where you’re lacking at one point. If you’re tracking the metrics, you can build in more content.

[00:25:12.090] – Chris Cunningham

Exactly. So stay on it.

[00:25:14.620] – Joran

That’s nice. How does the social media strategy integrate with the other channels you guys are doing? You mentioned you were content-heavy at the beginning. You started doing paid ads. I don’t know if you guys do cold outreach. How does it all fit in?

[00:25:25.490] – Chris Cunningham

Many ways. We work with all the teams. Number one, we take a lot of content doing well, and then we find a way to shoot on our shoot day, something that could be an ad, a really strong ad that we give to the ads team. That way it’s familiar faces, it’s the HR guys, but we find a way to bring the product in and still make it cool. As for cold outreach, we don’t have so much of using videos for cold outreach, but if someone gets warm and they bring up like, Hey, by the way, we love your content, the sales team will hit me up and I’ll say, Okay, let me make a video for you. We make a custom video for that champion who’s trying to get ClickUp at their company. It’s a cool way to run, Hey, look what ClickUp made for us. Have you seen these guys? It stands as it stands, that’s an easier way to close a deal. That’s how we bring it in bottom of funnel. We’re also very active on campaigns. If we’re releasing a new feature, I want everyone to know about it. I’ll make some funny content with those guys again, but also make really great content that teaches you the product.

[00:26:14.250] – Chris Cunningham

That’s where I mostly put on YouTube. A lot of people want to come and learn the product. I make sure they have that available. We do it in a cool way. It adds a tiny bit of humor, but it’s mostly just teaching them the product. I’m always trying to create a few creative videos, like something more wild and long form. You’ll see a lot more of that testing with ClickUp in 2025, really crushing the long form and maybe making it feel episodic or fun. We’re going to test a lot of things until we really nail that. We’re doing good on YouTube, not as great as our short form. I really want to be the best brand in B2B SaaS. The only way I’m going to do that is if we crush every single platform.

[00:26:44.350] – Joran

When you say long form, what do you mean in your terms? Is it going to be podcasting webinars or do you have any other things in mind?

[00:26:51.820] – Chris Cunningham

Four minutes plus. I’m going to keep doing webinars myself and then probably a podcast as well. What I really mean is something more like where you come, hang out. I look at everything as B2C, and I get ahead of it and bring it back to B2B. Think of a dude perfect. I’m not going to go as far as to say Mr. Beast, but the stuff that people watch more along, the stuff people come hang out with and really spend time with. I want to find a way to do that for business, and that’s not going to be easy. That’s not going to be a first try, second try. That’s going to take some swings. But everything good takes some effort. I think if I put some effort in, I really crush that, and I find a way people can come hang out, learn more about B2B, be entertained, then I’ll really, really feel very confident in what I pulled off.

[00:27:30.240] – Joran

Nice. Sounds interesting. I’m going to follow this. We talked about a lot of successes, how you got there, and things are working really well. But I can imagine you faced a lot of challenges while growing to 200 million impressions per month. Give me some challenges you ran into.

[00:27:47.700] – Chris Cunningham

Some of the major mess-ups for me was sometimes trying to not know everything about the product, to not study every release and being in sales, and that was really tough. I’ll give you an example of a mess-up. We almost took our a little too seriously. We made this one funny video that did really well on social, and we thought that everyone was going to love it. We had this video and we were presenting it at a dev conference in San Francisco, and it’s all developers. We had this video where it looks like it’s a demo of ClickUp in the middle. It shakes and cuts up and it’s me rapping. It was a pretty hilarious rap. It did well on social. We decided we’re going to do that at this presentation in front of all these developers in San Francisco. It was a big conference. We were happy to present. It was a big deal for us. We We played the video. I’ll never forget Zab and I were both speaking on stage. As soon as we played the video, you could hear crickets. No one cared. No one thought it was funny. No one laughed.

[00:28:41.420] – Chris Cunningham

I looked to my right and Zab had snuck off the stage. He was so embarrassed. He I had to continue. I had to keep it going myself. That was a hilarious moment. I think we got too cocky in the content. Just thought everyone would love it, but we didn’t know the audience or read the room. That was a pretty funny one. Where else have we messed up? I really think that maybe we also thought that right away when we got some money, that you just hire people from the top companies right away. Like, Oh, they’re at this company, they’ve got to be great. If I’m being honest, that was not the best play for us. Many of those are not with us today. They just didn’t work the same way we did. Maybe they got uncomfortable or lost the scrappiness. But a big fuck up for us was just thinking, Oh, we just hired some people from big companies. That’s probably one of the most major ones I can think of.

[00:29:20.300] – Joran

I love the first one where I just walked off the stage as well.

[00:29:25.840] – Chris Cunningham

He left me, man. I’m so embarrassed. He just slid right off and I’m like, Wait, I didn’t even notice because I was so flabbergasted. I waited for him to continue to speak and he wasn’t there. I was like, Oh, I have to do this now.

[00:29:37.910] – Joran

The advice here would be read the room or know who you’re going to present it towards to make sure it’s actually funny or not.

[00:29:44.510] – Chris Cunningham

Read the But just because you have one content hit, it doesn’t mean the world’s going to like it. He’s still going to adjust.

[00:29:49.540] – Joran

In the end, an event is probably going to be different also than social media, where people are taking a break on social media versus at the event, they’re not there to take a break. Exactly. Nice. You mentioned that you guys used influencers or have partnerships to amplify their reach. Can you tell a bit more what is working for you right now to leverage outside people?

[00:30:11.400] – Chris Cunningham

I love influencers. I’ve worked with them a lot, but I haven’t been doing it as much because I really like building this internal thing. What I’m doing is getting an influencer to create a new channel and then build that channel because I own that channel. I own that ICP. I like getting actors or whoever to create a new channel for me that I own. Then they still create on their page and they create new because I can adjust to what audience they want. I can build a new audience. And not every influencer has the perfect audience. That’s how I work. That’s my new thing. I do still like some of the LinkedIn thought leadership ads. We’ve had some success there. I also like getting an employee to create a post and then paying to boost that post. So getting an employee to make something value-based. It’s coming from a person at the brand and then boosting that. That’s some of the strategies I’ve seen in influencers that’s doing pretty well.

[00:30:52.440] – Joran

When you hire somebody to create content for you, you want to own the channel. So you’re going to put it on a channel which you own, where you can control as well.

[00:31:01.480] – Chris Cunningham

Yes, exactly. When I own the channel, it’s better because then, let’s say the creator, we don’t work together anymore. All good. It’s not over. I can just bring in another creator. The audience is still built. Those followers are valuable. That’s my new thing that we’ve been doing really well on. I have tons. Click on the street, ClickUp Memes. I have a new show called Almost Quitten Time, which is funny business content. What I do is I watermark and put ClickUp on there. People still see it as a ClickUp thing, but we’re creating it. I can still post those videos on our LinkedIn and things like that. Check out Almost Quitten Time. It’s a really cool show that we’ve created is doing really well.

[00:31:32.620] – Joran

I guess you mentioned already 2025. How do you see social media in 2025? You mentioned a mid-short content, or I don’t know how you call it, I guess, four-minute video that you mentioned. Any other things you guys will be doing?

[00:31:44.490] – Chris Cunningham

Yeah, I mean, I’m still going to… Short form is going to dominate me. So that short content is always going to be, or shouldn’t say always, anything could change. But number one, for now, number two will be that mid-level, that four-minute mastering that type of content. Have people come hang out, maybe even a 20, 15 minute. Have people come hang out. So I’ll be testing a lot of that. I’m I’m going to be on the look out for a new social media platform. I think we’re doing something new. I don’t know what it’s going to be, but around this time frame, there’s always something new. I’ll be watching out and keeping my ear to the ground for any new ones that come up. Also, I think really trying to find a way to put our product in some of that funny content. I think I can do that more. It’s going to be harder. It’s going to be more of a challenge, but I think there’s a way to do that. Lastly, I would say it’s more like just real content, not just me talking to this camera, but me walking out in quick cuts.

[00:32:27.670] – Chris Cunningham

I think content is changing a lot. It’s got to You’re going to have a very unique style. I think really adapting ours to be better will be a good one as well.

[00:32:35.210] – Joran

Yeah, maybe one other question because you keep mentioning the humor, right? I love it. I like watching the videos, but I think a lot of people, probably maybe research founders who don’t have a team, it’s hard to make a SaaS product funny.

[00:32:47.630] – Chris Cunningham

I don’t think everyone should. I’m not saying… Just because ClickUp is successful, it doesn’t mean everyone should do it. What I would say is start building in public, start trying something, start doing a podcast like you’re doing. Start doing something, start doing Start thinking about your customer. Maybe even just start interviewing your customer. That’s how I make good content for my customers. I interview them. That probably shouldn’t turn into a podcast. But I have Riverside not because I’ve done a podcast. Because I go interview people on ICP and I learn from them and ask them what I’m going to save it for later so I can go back and think of what content to create. I’ll make clips of it and post clips sometimes, but that’s really what I do. Start talking to your ICP, figure out what they like, and then start creating that content. It could be, or also think outside the box. What’s something no one else has done that you could do that your followers would like? Start doing that because if you just look and say, Oh, my competitor is doing this, that’s cool, and do the same, it’s not going to go anywhere.

[00:33:37.100] – Joran

We’re going to close off the podcast episode with two final questions. This can be more broad than just social media. What advice would you give a SaaS founder who’s just starting out and trying to grow to 10K monthly recurring revenue?

[00:33:52.650] – Chris Cunningham

10k monthly recurring revenue? Yeah. The first thing that I would do, I would get scrapped. I would almost follow something similar to we did. Right away, who’s I’m happy with the competitors? Who’s the one I can pick up? Find that low hanging fruit, figure that out, and then get a few clients. Just get a few people using the tool. Give it away. Give it away free. Before you start thinking about, I need to charge everyone, you won’t ever get to 10K because no one’s going to use your tool enough for you to learn. If you get away free, even if you have to lose a little money, you got to eat the money sometimes. Eat the money for a bit, figure it out. If you have to work another job, do that. But then from there, once you get to people using it, obsessive with them. Seriously, talk to them all the time. Build a candy board, ask people what they want. But we used to send these little quick surveys, like two We would start a survey of 10, and then we start voting. People are not going to fill out 10. But if we give them two, maybe three max, what’s the most important things that could change a company if we ask these questions?

[00:34:38.660] – Chris Cunningham

That’s what we would ask ourselves, and we’d send it out. We got a lot of people really got us a lot of answers. We take those answers. We come back and say, Hey, okay, we implemented that. What do you implementing. Show them you’re implementing, show them you’re moving fast, show them you care about their responses, put it into action and show them results. We’d come back and say, Hey, look, 80% of you want this. That’s what we’re doing. We’ll have it done in a week, and then come back to them. Show them how scrappy you are, and then sky the room. Then, what you do is once you get a lot of people in your loving and they see your mission, then all at once, send out a code, send out something. Pretend you’re not sumo for a bit. That’s what we did. We just said, Hey, look, we actually realized we needed money. We were trying to keep this free for as long as we could, but we need money to keep building and paying everyone. You get it. How about we offer you 60% off Now, knowing this rate will never be there again for a couple of years.

[00:35:19.240] – Chris Cunningham

You can get in early and say you were in early, people with ClickUp. That’s what we did. Way more people bought than we expected.

[00:35:26.120] – Joran

In the end, you ran your own LTE lifetime deal.

[00:35:29.910] – Chris Cunningham

We did. We ran our own.

[00:35:31.340] – Joran

Yeah, I love it. Let’s assume then we pass the 10K MR stage and we’re going to make a huge step towards 10 million ARR. What advice would you give SaaS founders here?

[00:35:41.810] – Chris Cunningham

I think from there, you got to get a little more relentless. I think you got to pay attention to every customer that comes in. You got to ask for referrals. You got to build. What we would do is we would get someone in a small team in Home Depot, and then find a way to close that team and then find a way to really go through that team and say, Okay, look, what would it take to get your whole company to use us? I see your marketing team, what would it What do you need us to do? And start getting whole entire teams using you. Even if you charge less per seat and hook up a deal, I think you’re really going to make some deals. It’s not devaluing your product. It’s getting more people on. It’s getting bigger, and then they’re going to tell more people about it. From that 10K to 10 mil, we really started doing a good job of infiltrating teams and just start adding immense value and then figuring out what you need to build, be very strategic in what you build. Then also find a really cool way, something that’s free where people can find you.

[00:36:26.340] – Chris Cunningham

Something that you can build and then just not charge for it. We did a little tool that would allow you to clip and things like that in your Chrome extension. We built a Chrome extension that we give away free. Find something that’s viral, that’s easy to use, that you can give someone, and they use it free and they start using your tool.

[00:36:44.530] – Joran

Exactly. Build a growth loop. Let me see if I can try to summarize. If you’re going to start out with social media, start scrappy, be different, add value, make them feel something, definitely engage with the comments, so don’t just put things out and don’t do anything after. If you If you want to use social media the other way, track your competitors, see negative reviews, start omnipresent experiment and test what is actually working, combine humor with educational videos, make it value-based, start wrapping during a demo. The key is basically, consistently, going viral. Don’t just do it once, but keep trying to do it, which is going to be hard. One way to do it is build in public. Linkedin is a great way to do it. It doesn’t always have to be the founder. You can use employee-generated content. Fancy videos don’t always work. Just do it with an iPhone or anything you have already. You don’t need to have all the fancy gear. If you’re going to track KPIs, start with impressions. And a great one you mentioned is landing pages per social to track conversions. Topleaderships both work really leverage your own tool. And then if you want to find things to post about, find a problem on Reddit, Cora, and then solve it via the post you’re going to put out.

[00:37:53.680] – Joran

Build a content calendar to remain focused. When using influencers, have you own the own channel, so make sure you actually own the channel so you can use it later down the line as well. If you’re going to go for the 2025 short form is going to be key, mid form is going to be something you guys will be experimenting with and you’re going to to breathe the humor into it. If you don’t, again, know what to do, interview customers, create content ideas from it. If you’re just starting out 10K MRR, find low-hanging fruit, find people who don’t like your competitor, ask for feedback and put it into action right away. 10 million ask for referrals to infiltrate teams and companies and build that viral loop.

[00:38:35.290] – Chris Cunningham

Nice. That’s solid, man. That’s a study guide I need to remind myself.

[00:38:39.710] – Joran

Exactly. If we want to get in contact with you, Chris, how can they-I’m really easy to reach, chris@clickup.

[00:38:46.680] – Chris Cunningham

Com, @cuttingham on Instagram and TikTok, and Chris ClickUp on LinkedIn and Twitter.

[00:38:52.130] – Joran

We’re going to add links to everything so people can just click on them. We’re also going to reference the Almost Quitting Show you mentioned. We’re really curious about that one. Have I haven’t seen it yet. Any final pieces of advice towards SaaS founders before we close off?

[00:39:07.190] – Chris Cunningham

If anyone needs help, I’m available to do consulting. I’m on intro. Com. If anyone needs help or want some strategy, it’s not easy to start, but it is easy to build a process and get it going. If I can help anyone, I would love to do so. I’ll send you my intro link as well. As for last advice, just don’t follow what everyone else does. Feel what you like, really start testing, and treat it like ads. Test for a while. We don’t give up after one week when it doesn’t work. It won’t work after one week. It’s not like we work after one week and things that do work will stop. It’s like ads. You got to refresh, you got to keep trying. But don’t give up because once you do get it, it is really worth it to have a brand that people know and care about.

[00:39:40.910] – Joran

Nice. Keep it going and keep having humor and fun in the meantime.

[00:39:45.000] – Chris Cunningham

Yeah, keep having some fun. Have some fun with it, too.

[00:39:46.880] – Joran

Nice. For We Realistic, please leave us a review on Spotify or Apple podcast so we can beat the algorithms. We are going to add a poll on Spotify. Let us know what you thought of this show. Thanks again for coming on, Chris.

[00:39:59.850] – Chris Cunningham

I’m Amazing. Thank you so much. Appreciate you.

[00:40:01.650] – Joran

Thank you for watching this show of the Grow Your B2B SaaS podcast. You made it till the end, so I think we can assume you like this content. If you did, give us a thumbs up, subscribe to the channel. If you like this content, feel free to reach out if you want to sponsor the show. If you have a specific guest in mind, if you have a specific topic you want us to cover, reach out to me on LinkedIn. More than happy to take a look at it. If you want to know more about Reditus, feel free to reach out as well. But for now, have a great day and good luck growing your B2B SaaS.