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Meet the Guest: Chris Cunningham

Chris Cunningham, an entrepreneur and business executive, is currently the Head of Social Marketing at ClickUp, a productivity and project management software company he co-founded in 2017. Born in Martinsville, Virginia, Chris graduated from Virginia Tech with a degree in Marketing and Management and a minor in Global Business.

Chris began his career at Cvent, where he quickly rose to become the youngest manager at the company. After Cvent went public, Chris moved on to run Fast Followerz, achieving over $50 million in sales. He then co-founded ClickUp, where he closed the company’s first major deals, including partnerships with Home Depot and Randstad. Under his leadership, ClickUp has grown to over 1,000 employees and has raised $535 million in funding at a $4 billion valuation.

The platform has attracted over one million users in its first two years and earned recognition as a top productivity app. Chris is known for his innovative approach to business and social media, helping to push a Super Bowl commercial and build ClickUp’s verified program. Chris is also a sought-after speaker, representing ClickUp at tech conferences worldwide.

He is dedicated to making project management accessible to everyone and continues to drive ClickUp’s success.

 
Follow Chris on Linkedin
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Podcast Episode Notes

Takeaways:

Here are some of the biggest takeaways from this episode:

  • Leverage Authenticity: Start incorporating more authentic, behind-the-scenes content into your social media strategy to build trust and connect more genuinely with your audience.
  • Maintain Consistency: Set up a content calendar to ensure a consistent posting schedule across all your social media platforms, keeping your audience engaged and informed regularly.
  • Use Data for Decisions: Regularly review your social media metrics using tools like Google Analytics or Sprout Social. Adjust your content strategy based on what’s performing well to maximize engagement and growth.
  • Explore Short-Form Videos: Begin experimenting with short-form video content, like reels or TikToks, to tap into current trends and capture the attention of your audience quickly.
  • Collaborate with Influencers: Identify potential influencers or brands in your niche and reach out for collaboration opportunities to expand your reach and introduce your brand to new audiences.
  • Encourage User-Generated Content: Create campaigns that encourage your followers to produce content related to your brand. This can increase engagement and provide authentic content that resonates with others.
  • Utilize Emerging Tools: Take advantage of tools like AppSumo to find new software deals, ClickUp for organizing your projects, and Vista Social for optimizing your social media management.

Mentioned Tools & Resources:

These are the tools and resources that were mentioned in the podcast episode:
  • Hootsuite – Social media management tool that helps businesses schedule posts, track engagement, and manage multiple social media accounts.
  • Canva – Graphic design platform that allows users to create social media graphics, presentations, and other visual content easily.
  • Google Analytics – Web analytics service that tracks and reports website traffic, helping businesses understand their audience and measure marketing effectiveness.
  • Sprout Social – Social media management and analytics tool that aids in managing social media presence, engaging with the audience, and tracking performance.
  • AppSumo – Platform offering deals on software and tools for entrepreneurs and small businesses, providing access to new tools at discounted prices.
  • ClickUp – Productivity platform that integrates tasks, docs, goals, and chat in one place, helping teams manage their work efficiently.
  • Vista Social – Social media management platform providing scheduling, publishing, engagement, and analytics tools for managing social media presence.
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    Episode Transcript

    Ashley Segura: All right, let’s get started when you’re not at your desk and you find yourself in the kitchen. What’s your go to dish to cook? 

    Chris Cunningham: Funny you ask. I am not the best cook. Uh, my girlfriend helps a lot there, but my go to dishes, uh, I like ground turkey, uh, just, I think it’s healthy. It’s clean. It’s very quick and very easy for you for me to make.

    So ground turkey is my go to. Um, and then maybe I’ll put in with like tacos or whatever else, but that’s just my easiest. I just made it before. For lunch earlier. So it’s definitely my go to. 

    Ashley Segura: It’s pretty safe to like, you can’t mess it up and I’m really bad at it out. You have to really try hard to 

    Chris Cunningham: overcook.

    You got to be really bad. So I haven’t done that yet. Thank goodness. 

    Ashley Segura: Okay. Searching from ground Turkey to ClickUp. So tell me more about your journey and what led you to co found ClickUp. 

    Chris Cunningham: Yeah. So straight out of college. You know, I knew I wanted to do something in business and tech and fast moving and sales.

    And I joined a company called C vent. That was my first job. And C vent is like, um, it’s like corporate events, right? All, all the parts of corporate events from, from planning to choosing your venues and I had a blast doing that. I rose up really quickly. I became one of the youngest managers there. The company went public, a lot of success.

    And I learned a lot, but during that time I was always working with. Zeb, the founder of ClickUp and we had, we were in college together. We were always doing something. We’ve managed a rapper. We, you know, I’d created a social media business and he really ran with that and dropped out of school as I went to go work at C vent, but even when I was off work, I was still helping him on that side with, with the agency at the time that we had, and from there we saw a lot of success and as I had gotten, you know, all my shares and everything and really reached what I thought was my ceiling is see that I wanted a new challenge.

    And even though I could have stayed there and probably became director and VP. I was just ready for something different, something fast paced. I felt like they were moving slower as they got in public. And you know, a lot of my ideas had to go through different meetings and people. And I just wanted to run and do things.

    So I talked to Zeb and I was like, I want to move down to Charlotte and I want to, I want to join this agency with you full time. And I did. And we grew that agency and it was doing really well, making plenty of money. But then Zeb had a near death experience and he, he was like, look, I don’t want to be these guys who just grow social media.

    You know, I want to be something much bigger than that. And that’s when we decided to create a social media app. And this app was called memory. And this is where the core team of really ClickUp first started. It wasn’t ClickUp was our first mission. It was really this app called memory. And what memory was, was a Snapchat competitor at the time.

    Snapchat was the hottest app out, but it would erase your memories in seven seconds. They were all gone. And we saw that as a major flaw. The best thing you have in life is your memories. So we created this app. We really, really felt strongly about it. We thought we were going to be the next Zuckerberg and Tom from MySpace.

    We really felt that was our calling and our journey until one day we woke up and saw the news that Snapchat had created Snapchat memories and basically took our whole idea and just made it a section of Snapchat and we lost everything, you know, all the money, everything invested. And, uh, that hurt our pride a lot, you know, telling, you know, you’re posting on social media, you’re telling everyone that you’re going to build this successful social media app and it fails, you know, in front of everyone.

    But I think that was really what we needed because then that’s when we had the urgency and said, okay, we have one last shot at this. What are we going to do? And we had two options. One where we were going to create a Craigslist competitor. I forgot the name we were going to call it, but we had some name basically what offer up and, um, those tools came up to be, we were going to create our own version of that.

    I’m glad we didn’t go that route. And the other ones we decided maybe to take on project management because. We had built our own tool internally. Zeb really hated most project management tools. He hated the way they made you work a certain way. He hated that, you know, most people would use different ones.

    So you’d have to log into this one to work with this person, another one to work with another person. And he just thought it didn’t make sense. And they weren’t customized well enough. So even though the harder challenge. Was going into project management because there’s already so many companies who are very well off, who had a lot of employees, a lot of funding, and we were just four people.

    Uh, we decided to still go after that mission. And so in Palo Alto, we had moved from Charlotte to Palo Alto. We all lived in a house and we put everything we had in, into this. And that’s where ClickUp kind of was born. 

    Ashley Segura: That’s such a incredible journey and so many different pivots in that. And I feel like that’s very relatable for anyone who’s in marketing.

    You’re constantly pivoting and having a move, whether it’s from branding to messaging. Uh, before we got on the show, you had mentioned something about achieving 200 million organic impressions in a month. I would assume there’s a lot of. Pivots to kind of get to that, but can you break down what this goal is with 200 million organic impressions in a month?

    Chris Cunningham: Yeah. So 200, 200 million is my goal. I haven’t hit it yet. Um, it’s, it’s a, it’s a major goal, but I have gotten, we just hit 75 million, which is still a pretty big stretch goal. So. The goal is to get 50 first, you know, and then as we, as we kind of scale, then we’ll readjust and, you know, either put more, create more shows.

    So we hit 50 and then we really even just passed 75. So this, these HR videos are doing really, really well and getting an insane amount of impressions. And it’s probably more than that. If we count, you know, someone showed me that the. Part three went viral in China on their version of YouTube. So there’s way more.

    I don’t even know what number we’re fully at. I’ll catch up soon. But I think the, the pivots we had was that at the beginning, you know, we really didn’t focus so much on TikTok. TikTok wasn’t our major app. It wasn’t a major play. Um, and that no one in B2B really has that much. I mean, there’s a little bit of Duolingo and.

    A B to B companies put a ton of focus into it, which I saw wide open opportunity because it’s the only app where you can start something new and just get so many views. And it’s a great place to test. And to me, short form content is just, it’s the future. So whether it be Tik TOK, even a Tik TOK gets banned, it already happened in India and all those views just shifted to YouTube shorts and Instagram reel.

    So I think for me, it’s. Really about building a short form content machine. But yeah, we didn’t have a lot of pivots. At one point we were really focusing on Twitter and that’s where a lot of things were coming in for us and a lot of signups. Uh, another time we were focusing on, um, you know, Instagram and parts there.

    So I think now it’s, it’s really tick tock first and we’re still doing a lot of things on Twitter and LinkedIn, but. And it’s where the majority of our views come in and, and then we can still repurpose something that does really well on TikTok to Instagram reels, to Facebook reels, to LinkedIn, uh, to YouTube shorts.

    So it works really well for us to put a lot of our time into that content. 

    Ashley Segura: Yeah. I mean, short form content, it’s, it’s funny how Before the very beginning of like the whole online world, everything was long form content and you actually wanted to read it and want us to digest and get all the information and then slowly things got shorter and shorter and shorter and then video took over and then it was long video, then short video, and now even 60 seconds is like debatably long for some people to be able to watch a minute of video.

    So short form is for sure the future, but why impressions out of all the metrics, why impressions? 

    Chris Cunningham: Impressions is the easy one for track for now. It’s not like we’re, it’s not, we don’t care about signups and things like that, but the way we see it is if you just start off your content, if you just, and this is a big comment I’ve gotten a receipt from people as we’ve had the successes, Oh, well, you know how much, what is it driving for signups?

    And it’s like, if you just create content, just tracking signups from the beginning, you’ll never get these kinds of views that I’m getting now. And you’ll never get people talking about the brand like they are now. So I think you, you start with that. And obviously I’m still working to. To figure out the best strategy to do that, but I’m not going to hinder all the hard work we’ve done by all of a sudden in my HR videos that are getting millions of millions of views and showing so many people every day with ClickUp is who didn’t know who we are.

    I’m not going to start ruining it just by shoving ClickUp, you know, in the content, as much as some people. Could like that or think that’s the smartest play. But what I will do is I’ll find cool ways to bring you back, or this is top of funnel. You know, I’ll catch you middle of funnel. I’ll catch you bottom of funnel.

    As long as you know about us, when you’re making a decision, our goal is just to make sure that you’re, that we’re in the playing field when you’re making a decision for project management. And so by having great content and by being out there, that’ll help, but I still need to create great middle of funnel and great bottom of funnel content.

    But right now it’s, I’m trying to take this top of funnel as big as I can get. As we’re doing that, I’ll work with the amazing members on my team to find better ways to incorporate the brand, incorporate proper call to actions, but without hindering the growth. Cause right now we’re on a path that, you know, no one’s really accomplished in, in B2B and I want to see that through.

    Ashley Segura: Definitely. So let’s break down strategy. How many videos are you producing? How much effort are you putting towards video versus content on the site? Like where are all of your content efforts right now? 

    Chris Cunningham: For me, it’s, it’s mostly the short form video. I mean, we have an entire team. Um, we have like a producer.

    Uh, it’s very scrappy though. We have like a producer who kind of also films and edits. We have, uh, the main talent, Luke, who mostly will is, is acting and scripting, but also will edit as well. Then we have Adam, who’s the other guy you seen. Luke is a. blue, blue polo and Adams, the other bald, handsome looking gentleman who’s dancing along in those videos, but he’s also like an associate producer.

    He’s editing. He’s coming up. He came up with the idea itself at the beginning. So, and then we have stormy who kind of post everything is also in the writer’s room. So I was five. We’ll meet on Monday mornings and we’ll kind of go through for an hour and a half, two hours. We all bring ideas to the room.

    We all have thought about these ideas better than before. We bring our best ideas and then we all present them to everyone. And we kind of riff on them as we’re in the call, like, Oh, what if we did this and this? And at the end we choose, we all vote and you can’t vote on your own. No, it doesn’t matter if you get no votes at all.

    We all vote. And then the ones that get the most votes, we pick. And then we shoot that week and then we analyze at the end of the week. So we’re, that’ll answer that question. That’s like the process. And then for, as for how many we’re creating on the ClickUp page, I’d say we’re posting like one a day, one a day is kind of our sweet spot.

    We, we try doing two and three and. I haven’t seen that much advantage. I’d rather have a really good video and post once a day and just keep it consistent, but now we also have more channels, right? So we have ClickUp. We have ClickUp comedy where I’m testing new creators for, for funny stuff. We have ClickUp memes, which is a mean page that’s growing really well.

    And, you know, hit almost 20 million impressions last month. We have a DIY page we’re creating next month. We have a man on the street page. Uh, and Luke, the same talent is also working on the man on the street. So they have like, in reality, they’re creating like. Uh, enough for two or three videos a day, but we’re doing them in different batches.

    So we’ll go shoot on like a Wednesday at the office and then maybe on like a Thursday they’ll go do man on the street and then that’ll give us enough content for the week. And then some Luke can just shoot a home really quickly and, and things like that are, uh, but it’s, it’s very fast. It’s a lot going on.

    That really comes down to the writer’s room and then analyzing at the end of the week and really riffing on things in the middle. 

    Ashley Segura: So how are all of you coming up with your own topic ideas? Thanks. 

    Chris Cunningham: You know, we all kind of just, we all have our own styles, our own things we like. Now, obviously I’m coming in more with, with ideas to come off.

    Like right now I want to ride this HR thing. I want to do it as long as people love it. And I’m not, you know, so arrogant or, you know, so to think that it won’t last forever. I know that, you know, this, this, this could get extinct. So we’re always testing new ideas. So whereas we’re, we’re always running as far as we can with things that are working really well, always still testing new things.

    Like we have a corporate jargon series is doing really well behind. It’s not getting 15 million a video, but it’s still getting a million or two. So it’s. It’s a solid one and maybe we can make it better and get it there. Um, but we’re all kind of looking at our own. So we’ll look at a few that are successful.

    The formula we kind of do is we have A’s we’ve, we call it the ABCD formula, A’s are a really good videos. One has already been successful. Something we’ve done that’s hit it 600 K or 700 K plus. We’ll find new versions of that. B’s, B’s are kind of just like, um, something maybe we’ve seen elsewhere, but we think we can do it in our own way.

    That’s like a little different, like maybe something cool. That’s, Or just an idea that we’ve seen in content C is, um, riding a trend. So, you know, like, Oh, we’re project managers. Of course we. That trend will jump on those, uh, but not too much. I don’t want to be that brand. It just depends on trends. And then D is my favorite.

    These are just coming up with something completely random that might even not even make sense. You know, like just something that no one else has done. And you’d be surprised how many of those turn into our A’s because I’m, I’m learning that the more kind of random and ridiculous you can be on social media, like just so.

    So, so I grabbing a different that that will grab you more attention. 

    Ashley Segura: So then what is the, what’s the idea behind creating these different platforms or excuse me, different profiles with different themes? Is it all to get more brand awareness to the brand name? And then of course, eventually in goal is conversions and signups and whatnot.

    But. Why you guys are scrappy, you’re four, four or five people ish, which, 

    Chris Cunningham: yeah, 

    Ashley Segura: yeah, exactly. So that that’s small team, a lot of, of resources being put to this. Why spread it out across different profiles? 

    Chris Cunningham: Yeah, because we think that you can only post with so many times on ClickUp a day. And it’s not that now this, this main team is working on the ClickUp on the ClickUp channel.

    So just to kind of, I guess, clear up any confusion, the writer’s room is for the ClickUp channel. Now sometimes we’ll bring in the other creators for their channels, but I have, it’s, it’s a different team. So I have like some meme experts who are working on the meme page. It’s my, I’m usually working with all of them along with the producer with each other page, but for ClickUp, which is where we think that’ll get the most views, which is getting the most views.

    We put the most attention there. Or let’s say we have a down month on ClickUp. It’s nice to have other pages that are slowly trending up. So these are all testing. We could. We could decide to scrap them all and just focus on ClickUp. But right now ClickUp has like a growth like this, and then maybe it’ll come down and up like this.

    The memes have like a steady growth and then we’re going to keep taking bets. So we’ll see if we can continue growing other pages, it’s worth our investment because we’re not spending that much overall when you look at how many impressions we’re getting. So it works out really well. And the more we can get, the better, the more attention I can take over, the more different spaces I can get on social.

    Why, why not go after it? 

    Ashley Segura: I think this is something that like you’re, you’re just fully nailing it right now on how there is an idea, test it, put resources behind it, test it. Especially if it’s not a costly thing, especially if you have people who have expertise in it, why not test it? So what would you tell a brand owner or a head of marketer?

    Who is like, you know, I want to test this new outlet, but I don’t know if we’re going to have budget for it. Or I don’t know if I’m going to get approval for it. Like you guys are clearly. Ready to go at all times to test things out and have the mentality. But most brands and departments are not like that.

    So do you have any advice for people who want to test many different outlets, but have that kind of halt of, I don’t know if it’s going to work. 

    Chris Cunningham: The key is you never know if it’s going to work, right? Like everything I’m working on today could be off tomorrow and social changes, but. The advice I would give to anyone and kind of what I did is I just said, Hey, look, I’m going to take a tiny bit of budget and work with this.

    I started, it didn’t, it didn’t just start like all like this. I brought it up in pieces. I was like, let me just work with a creator, not full time. Let me just, let me just contact a creator and show you how much better he can do than what we’ve done historically on tech talk. And then I showed them some success.

    And we had a video that hit maybe. You know, 5 million and 2 million. They’re like, okay, this is really cool. Okay. Now let me, you know, let’s, let’s bring him in more serious and maybe let’s bring in someone to help with him, you know, and then we had a little more success. So I think you take steps and show success because like everything good in marketing, whether it be an ad, whether it be a new social channel, whether it be a blog, you know, a podcast, whatever you need to show some success, no one.

    No one’s got a success right out of the gate and anyone thinking differently is just, you know, really hurting themselves and the chances on taking risk. But when you look at everything good in life, everything good that we talk about in here at B2B, ClickUp as a whole was a risk, right? Like, so I think luckily we’re very forgiving and taking risk.

    As long as you take calculated risk, you do it scrappily, just like we did the beginning of ClickUp. You do as crappy as you can. You spend as, as least as possible, but still putting enough time and effort to get the outcome. And even if you know that, Hey, I need to spend more to get the real outcome. But if I can show.

    Steps and things coming towards that success. Then of course, any good marketing leader is going to say, okay, I’ll give you more budget. Like you’re, you’re going up. This is trending in the right way. Let’s. Let’s keep it going. And of course you have numbers in mind, you have CPMs in mind and you think, okay, this is still, this is a great cost for what we’re getting.

    Let’s keep it going. Let’s get more. And I think that’s kind of how, how I went about it and, and how every team should do it. 

    Ashley Segura: Yeah, definitely. And, and kind of have a bit of an open mind, but also reporting, reporting’s everything. So how often are you looking at analytics? Is it on a weekly basis? And then also how long are you tracking a piece of content to determine if it’s actually going to be successful?

    Chris Cunningham: So I’ve tried almost every software out there and honestly, none of them have worked properly for me because they’ll track the numbers, but then it won’t have the proper integration with one of the platforms and then they won’t track the old growth and maybe they’ll miss if Instagram also shares it to Facebook.

    So what I do is I just do it the old school way and we have a team and They will sit and look at this. So I’m tracking every Friday. I do a weekly report. I write it to our CEO and our CEO and the whole team. And, you know, I tell them how well we’re doing, whether it be good or bad, but I’m coming in. I have a tracker where they can come look at it, but I also break it down for them.

    Tldr and to say, Hey, this is what’s really working well. Doing great here. This is, this is the bet that I’m making for next week. I show them that I’m taking bets. I show them how I’m thinking and I show them what’s working and if the bet didn’t work or if it didn’t, but I show them the logic behind it and how much financial I’m putting into it, what, what success is coming out of it.

    But yeah, to answer your question, I’m tracking everything. All the time, including like, you know, when you have a video that hits 17 million views, of course, your other videos go up and that’s still, that’s still count. So we’ll go back and count those two. So it’s a little bit annoying to have to manually go back and say, okay, the video was here Monday.

    Now it’s here Friday, but it’s well worth it because I really want to understand the residuals of an amazing video. 

    Ashley Segura: So then how, how are you tracking the path to conversion from that? Are you just mainly collecting impression data and seeing what the most successful videos are, or are you able to track all the way to the conversion path and see where the signups are coming from?

    Chris Cunningham: I’m not even trying to track conversion at this moment. Like I have, I do have a, uh, a landing page. It’ll track if someone comes to tick tock and, you know, goes into our bio and that’s, that’s tracking. So that’s doing really well, but, but we’re really not so concerned. Like that’s not what we’re. That’s not our, our main, our main thing right now.

    We will find ways to do it in there, but we feel like if we start pushing too much, it’ll take away. So right now we’re, we’re going after impressions. We’re going after eyeballs. We believe very strongly in our middle of funnel and bottom. And our main goal is just to be known and the space and compete where people forget that ClickUp has been around a lot less time than most, all the major competitors in the space.

    So for us, it’s more just, we, we want to be in there and battle. We know we have a better product. You know, we’re very confident in our pricing and what we’re building and how fast we innovate and how fast we’ve been able to come into this space. So our goal is more to be seen. That’s not to be said that we won’t track.

    Like I’m still have, I still have data teams coming to me, um, and showing where we can see rises and kind of timing with, with the videos, which is great. But I’m not being held to anything like that, which is kind of the beauty of why I think I’m winning. I think if I was being held to, do we get 20 signups?

    Do we get a hundred signups? I think I would have to change the content to get the signups higher. But then the long run, who’s to say it would actually be higher. If I was just tracking on that, because we don’t know how many people finding and then going to Google. I think rather than harping over that and being like every other brand who’s losing on B2B, I think we’d rather win and then figure out other ways to come back in and track perfectly and properly.

    Like I could do a giveaway tomorrow and do a cheesy thing and see exactly how many comes from that. But I think it’s really just not our style. I think I’ll, I’ll, I’ll build custom landing pages. I’ll lean on the team to come with me always. But I think they’re saying you keep building your thing. And then we’ll figure out how we want to perfectly track that coming in.

    But the board is also, you know, I think they’re also in value of seeing what 200 million impressions is. Versus just signups. Now, of course, obviously always care about signups. It’s a, it’s a huge part of, there’s other pieces of content I’m creating for that. 

    Ashley Segura: Okay. So then that, that’s a completely different kind of department and mindset then.

    Chris Cunningham: Not as a clue. I mean, it’s, it’s not a different mindset. Like I, I care about it, but there’s, there’s teams whose focus are going and tracking the signups and I’m not going to spend my time doing it. My time is, I think what ClickUp does really well is. I will spend doing time with what I’m doing best rather than me trying to do this and spend this plate of making amazing content that gets tons of views and also going and doing something I’m not good at.

    I’m not a pro at. At tracking content, but there is teams who are, um, so we’ll leave that. We’ll leave that to them. 

    Ashley Segura: Know what you’re good at and lean into that basically. 

    Chris Cunningham: Well, yeah, it doesn’t, I mean, it really doesn’t make sense for me to go do amazing things and then go spend hours and hours. I’m an expert.

    I’m studying every week content, how to get better content. There’s other teams who, who study every week, how to be the best at data and everything else. So I’ll let them. I’ll let them focus on that, but they’re having a lot of fun, you know, seeing these come in. There’s always the beauty of like the sales teams coming to me and saying, Oh my God, these get brought up on everything.

    Gartner brought up our, Videos last week on the call with them. Um, you know, HR said they’re getting so many inbound applicants. They don’t know what’s going on because people want to work for the company, making this video. So there’s always cool residuals like that. There’s also the cool brand sentiment of seeing more people hop on and defend ClickUp and talk about ClickUp and the reshares.

    Um, so I think that’s a lot that you can’t track, uh, that, that we’re also very, very stoked on because we want to be a cool brand. We know we have a good product. Being cool was a whole thing. You can’t really put a financial number on. 

    Ashley Segura: No. And the brand loyalty that comes from that is something that’s going to last for a really long time.

    And it’s only going to grow as you continue to do this, especially experimenting with like the different channels and different profiles. And. Different themes of content. A lot of brands are so focused on just that in conversion goal that they completely miss out on this opportunity to build brand loyalty.

    And you guys are doing it for a B2B company. This is something that’s like, you know, this isn’t a new car. This isn’t something that’s like. 

    Chris Cunningham: Yeah. Yeah. 

    Ashley Segura: It’s a project management tool and you’re able to actually have people sticking up for the brand. Like that’s, that’s very impressive and something that a lot of marketers forget about when they’re identifying a new strategy or working on new campaigns that brand loyalty can exceed conversions in the long run.

    Chris Cunningham: You know, I think, I think also too much that people don’t realize that you have to take a bet on something. Like you look at the podcast, like we’re doing here today. Five, like five, six years ago, if B2B companies would have went hard on creating a podcast, you know, like who knows what it would have been if they would have sort of stuck with it and got there.

    So I think I’m taking that same similar bet on social media. I’m going to stick with it no matter, uh, no matter what, because I really do feel like things are going there. We spent so much time there. Uh, and I, I think B2B is, is behind there. So I would love, you know, I love being ahead of it and going to win, even though I still have a long way to go to be where I would like to be, it does feel good to, to take this bet that I feel strongly on early.

    Ashley Segura: How do you, how do you stay motivated though? Because you guys are producing so much content and you know, like I’m recording videos every single day and some days I’m like, yeah, I’m loving this, like this is where I’m supposed to be. This is awesome. And then other days it’s, it is a chore. Like, how do you personally stay motivated to keep creating new content?

    Chris Cunningham: You know, maybe it’ll change, but right now we’re having so much fun. I mean, we’re having so much fun in the writer’s room. We’re laughing. I mean, look what we’re doing. It’s kind of ridiculous, right? We’re bringing in like top songs from nineties, two thousands or whatever, and then bringing it back into HR and making it fun.

    Honestly, we’re having too much fun to think about it yet. I’m sure like with everything, it can get boring. If I, I’m sure if I was doing a podcast like you and interviewing every day. It would be tough. I think the, the key that I foresee maybe doing that is it’s always, always changing, um, always finding, you know, new, new, new things to dive into.

    It’s very easy to get stuck on one type of content, having one win. I think that creating like, you know, healthy, healthy, fun rewards for our team is really good to, you know, having something to work towards. Like right now, like we’re, we’re celebrating. We have 50, 50 million. We’re celebrating at 75. We’re celebrating when we crossed 150.

    A thousand followers on Tik TOK. You know, we’re celebrating as we’re beating these insane goals that, that seem so, so far away, just three or four months ago, but at the same time, we’re also like not happy because we, the way we’ve set these goals up or that we, they need to be consistent. Right. So like my COO is very intelligent.

    He didn’t give me a goal. Just hit this number once, hit it for three months, we make this a machine. And if you hit a one said you had, you had some good runs, but make this something that you hit consistently. And then as you do that, Then I know what they’ll do. They’ll challenge me to go do as long form.

    They’ll challenge me to do with written and, and I, and I welcome the challenge for, for all of that, because I do want to be. You know, I really want to win in this space. I really want to be known, uh, as someone who’s really taken some risk and, and succeeded, but there is a lot more work to do that. I’m definitely not doing as good as I could be on long form.

    Um, and I think also tying the product back in, in a cool way is another big challenge. So, you know, my work is far from done. I’ve accomplished something cool. I’m enjoying the run. I’m enjoying talking, you know, on these, these podcasts like this today, but I’m definitely still heads, Heads down and very, very focused on, you know, what, what can come.

    Ashley Segura: Are you finding any other types of content like, like being on the show today, uh, that’s helping get new eyes on the brand or is most of your time investment really focused on creating new content organically through the profiles? Like, Have you found any other unique sources that have really been great to help hit that organic impression goal?

    Chris Cunningham: I think, uh, the building in public, I just started creating that, but like speaking this goal out loud. And I think that got me a lot of podcasts. And I, you know, I’ve done a lot, done a lot this week, a couple today. Um, I think that has really helped get some attention because I’m, I’m being very open and showing the behind the scenes.

    Uh, so I will continue to do that and see it’s very new. So I can’t, you know, promise you there. I think, um, I think we’re adding some humor into our releases. Uh, we haven’t launched it yet, but you know, every week we do like a release video or it’s like, Hey, this is ClickUp 7. 3, you know, dah, dah, dah. We released X, Y, and Z features this week, and now we’re adding in some of our comedy into it.

    So I can get back to you on, on how that works. So I think we’re, we’re, we’re definitely still testing to see how far this can go. I think there’s more guerrilla marketing we can do with this that we haven’t done yet. I just got off a meeting right before you and I jumped on speaking about ideas. It’s like, how else can we take this?

    Further to like some live events and things like that. So I’m seeing a lot more. I want to start my, I’m going to start my own podcast as well. Like I, I think this is fun. Like even with, uh, with you, I spoke to Eric from hatch earlier, did a podcast with him, and I think I learned so much from the questions being asked that, uh, that really opened my eyes as well.

    So I’m enjoying not only that, you know, your audience will see this and hopefully add value because. I can tell by the questions you’re asking, you know, you care for your audience to learn and I care too. I want everyone to start having fun and B2B content. So I think, uh, I think this stuff really leads to some beautiful things because at any time, if you’re, if you’re really giving value to the people that are listening or going to listen to your podcast, It wins.

    So I want to create more value based content on top of just making people laugh. 

    Ashley Segura: Yeah. I mean, getting people to laugh is like that first touch point and, and kind of warms them up and then to really keep them connected is that educational aspect. And in B2B educational content is something that We’re all used to, that’s a familiar space, but lots of times brands just see it as another blog post.

    Let’s just do another blog post and keep going through that. So really stoked to hear that you guys are coming with this innovative approach, testing lots of different things and honestly just running with it. That’s such a unique angle that we’re not seeing from a lot of B2B brands these days. 

    Chris Cunningham: You know, I feel blessed.

    Like I love that, uh, Zeb and Gaurav are, you know, founder and then COO. I think it’s, I am very blessed to allow me to, to take these risks. Cause I am very cognizant that not everyone is able to do this, but I do, I do challenge people to start trying some on your own, you know, like there’s a few things that I did rogue that, you know, before I got approval, I just started testing it and, You know, ask for forgiveness later.

    But I said, look, I did this, I took back what we usually spend on an influencer and I did this and here’s my success and I really believe in it. I think if you come in with passion, if you come in with testing something, no one’s ever going to be that mad at you for trying something new, especially in a space where everyone’s already doing the same thing.

    So, you know, I do challenge everyone to, to try something new and, and don’t be afraid, but you really do need to put your time into it. You can’t just, you can’t just really, um, halfway do anything and expect to see something you can do with a halfway budget. But you can’t with halfway energy. You got to put all that in there.

    Ashley Segura: A hundred percent. I love that. You can do it with that. 

    Chris Cunningham: Yes, you should know where that came from. 

    Ashley Segura: That was fantastic because it’s so true. I mean, if you start a project and you’re like, okay, I’m being pulled in a thousand different directions. Sure. That’s normal. That’s every marketer right now. But if you finish something through and fully execute on it, even if you only have half the budget, that’s where you’re going to be able to see the most success.

    And even if it doesn’t happen, you’re going to learn so quickly what didn’t work and how to pivot from there. 

    Chris Cunningham: And there’s a lot of, there’s a lot of beauty in that too. There’s a lot of beauty in learning and moving on and saying, no, right. It’s like the essentialism. Like, as long as you learn what not to work on, you’re still getting closer to what you should.

    Ashley Segura: hundred percent. Well, as we wrap up, I would love to hear what your secret sauce is at the moment. What’s your current strategy, maybe a tool that you just discovered or a book that you just read, that’s like just changing things for you. What’s your current secret sauce? 

    Chris Cunningham: My secret sauce is a friend of mine that I found earlier that used to work at ClickUp, but he’s so successful now he’s doing his own thing.

    Uh, Devin McPaul has found a way to really use AI to not create content. I’m actually kind of more against, not against, but like if you use AI too much to create your content, it’s going to sound like everyone else. But Devon has found a way to use AI to kind of like pull the data points of what people are talking about and what’s hot and what’s doing well right now.

    And I, I, I, I’m just really plugging him in because he’s doing it for me as we speak. And I haven’t even fully seen all the results, but just from the early things he showed me, I’m like, wow, this saves a lot of research time. Um, so I think that’s. That’s like kind of the secret sauce that I’ve seen right now.

    Let me think. Is there any other tools that I’m really, uh, I think this to social has been really good for us in posting and pulling data. It’s a much cheaper alternative to, um, uh, what’s the sprout social that we were using? Yeah. Um, sometimes we still use that for like, uh, the, the responding inside, but you know, it’s like dash, dash shots and all these really expensive tools.

    Whereas I think this, the social has been a really good one that for like 40 a month does most of the things. So I’m very. Impressed with what they’ve done. And I’ve definitely, anytime someone is really good, I’ll speak, speak their praises and then always check out app sumo. I think Noah Kangan does a great job of finding tools like, you know, so using Calendly, uh, I can use tidy cow and just pay one time and be done for life and they really innovate.

    So those are the three. The three things I think are really working and look out for more. I think I want to, I’m trying to work with some other big creators to start a community where we talk about this and social more, because I think a lot of people need to be seeing trends, trends, trends change so fast, as you know.

    Yeah. So look out for that as well. But that’s, that’s my main hacks. 

    Ashley Segura: Awesome. Thank you so much for sharing. Definitely keep me posted when you create that community, happy to add it into the show notes. But once again, thank you so much for everything that you shared. This has been really helpful. 

    Chris Cunningham: Yeah, I actually had a lot of fun.