Becoming a thought leader at one of the world's most successful project software management companies is no easy feat. Chris Cunningham is now the head of influencing marketing at ClickUp, but what most don't know is that he began his career as a sales representative at a small company.
In the second episode of our podcast, Chris outlines the beginning stages of his career and the company's unique approach to influencer and value-based marketing, a strategy that is seeing ClickUp now becoming a household name.
Who Is Chris Cunningham?
Chris Cunningham is the head of influencer marketing and a founding member of ClickUp. After completing his undergraduate degree in marketing, Chris went on to become the youngest manager at Cvent, before moving on to ClickUp. He relocated to Silicon Valley where ClickUp's employee base quickly grew from 4 people to 1,000 people.
Spotlight: You grew up in a small town and then later moved to LA. Did you ever imagine yourself ending up as a head of marketing?
Chris Cunningham: When I was young, I don't even think I had much of an idea of what marketing was. I'm from a very small town called Martinsville, Virginia. I had super humble beginnings and always knew I was going to do something with talking. I was always told that I was good at talking and that I was very social. A lot of things came to me by being a good communicator. I always liked to speak and try new things.
I just started diving in. Right after college, I went to work at a company called Cvent as a sales guy. I was there for four years and then went to go work with Zeb, ClickUp's founder and CEO, who I knew in college. Even with that, I still wasn't a marketer. I was kind of a jack of all trades while working for Zeb. I was our first sales rep and customer service. We would do little things in marketing, but it was all of us. You know, we had four employees to start. So, I never dreamed of this, but I think I always knew I would do something.
As I got more into my career, I realized that sales wasn't what I loved. I loved the marketing part. Now I'm so grateful that I can do that and have such a cool position at ClickUp. I couldn't have manifested it better.
You've worked at a variety of companies throughout your career. What would you say was the most important thing you've learned at each of these experiences? And how have they influenced your approach to marketing today?
At Cvent, I was young and that was my first career. I think what I learned there is how a company works and what it's like to be at a big corporation. When I joined Cvent, it was a couple hundred people and then it grew to a couple thousand very quickly. I joined at a great time and watched them go public. I moved up from being just a smaller sales rep to one of the younger managers at the company. I learned how to manage a team and what it looks like to see a company grow. And I'm so glad I did because now I'm seeing ClickUp go through that same growth.
AsI'm looking back, I'vemainlyworked at Cvent and then for Zeb. We had a social media company and there's where learned, I would say, how to be scrappy because we were a smaller company and starting to get a lot of clients.
What I learned at ClickUp was that anything can be done if you spend your time properly. There's a saying that if you study your craft for just 20 or 30 minutes a day, you'll be a master in no time. And it's so true. So many people just won't take the time to do that. But there are so many resources between ChatGPT, podcasts or YouTube. You can watch thought leaders in your space and learn from them.
What I learned the most from ClickUp is that you can learn anything, you can accomplish anything. And how to manage my time. The key is knowing how much you can get out of your day and those lessons have been immensely important for me. I can't express enough how much I hope everyone else can learn those too, because things in my career are so much easier now. Challenges don't seem as tough because I know how to break things down and how to spend time properly.
Do you have any advice for some of us on how to spend our time properly? What does your day to day look like?
Really good question! If it'sa very long project, something where I know I have to build an entire plan for like two weeks, that's something that I might not get started. But what I do is typically just set time. I'mvery big on time blocking. I'm sure people have heard of it, but if not, time blocking is huge. All my time is set, I put the exact task in there. Not to plug ClickUp too much, but I know exactly what I'mgoing to work on. I know that at 11.30, I'mgoing to go and work at this and I have it prepared.
I typically always get more done once I get started and get moving. Your brain is like a muscle. The more you get used to using it and diving into those tough tasks and getting something done, the easier it is. Sometimes just getting started, just sitting and making sure you have no distractions, no phone. I make sure that my notifications, like Slack notifications and clicking notification are off. You know, I can just dive in. I check my notifications during my time, and I set time for that as well.
I also know when to delegate. So many people don't know when to delegate. Make sure you grow a team that can help you, but make sure you're not toomonotonous. If you're also taking too many calls it's difficult to get creative because that also takes some time. So make sure you mark that time too.
You mentioned Zeb, but what else was it that inspired you to join the company? And what was it about it that really caught your attention in the first place?
Well, I was here from inception. I was already working with Zeb on a prior company with social media. Then he met Alex Rekowski and he knew he wanted a bigger legacy. He wanted to do something bigger thanjust growing socially. He wanted to actually change the world. We had about eight employees at the time and he offered for all of us to come to ClickUp, but he also told us it would be very hard. We would be working very long hours. We would have to move to California because we were moving to Silicon Valley, to start-up land. Honestly, I believed in Zeb. I understood project management a bit because we used it, but I knew that it was a bigtask.
A lot of our advisors said “Hey, you should not go into this space. There arevery big players. There are people like ex-founding members of Facebook in this space. They have a lot of money. They have a lot of funding. You guysdon't. It could be tough.”But I really believed that we could shake this space up. I think I spent a good chunk of my time just building ClickUp before we even got started. I just believed in the journey. I knew that we couldn't get paid much in the beginning.
I was more betting on ClickUp winning for the long-term. I believe in Zeb as a visionary. I also loved the opportunity of knowing there's so much I can learn. I wanted to be a part of that journey. I wasn'tgonna miss that no matter how tough it was. And it was extremely tough, but obviously it paid off. It's still war. We still have a lot of battling to do. The space is still extremely crowded and getting more crowded every day. So for us to stand out, there's still a ton of work to do.
How would you say you are working on standing out right now in terms of your marketing, for instance?
So many different ways. One thing we did just recently that was quite successful was that we dropped an album, which may sound ridiculous and different, but we were always into music in college. So we released an album called "Workflows by ClickUp" on Spotify and Apple Music. It has over a million streams. So it has been successful, but we spent hardly any money on it.
We have a couple of people who work at ClickUp who are very talented in music, especially KJ Hartness, who was the artist that Zeb and I managed back at Virginia Tech when we were in college together. He works for us as a creative coordinator. He does content and helps with influencers, but he made a lot of different tracks and we also got some pretty big artists on this.
Artists who are signed to Post Malone that are on tour right now, like Clever, Michael Minnelli, and this took off really well. We debuted it during our level-up. We wanted to have good music and make our conference very fun, so I used that as a double entendre to release this album, but also play interesting music throughout so the conference isn't boring like everyone else's. That did really well.
Some of the things we're doing are working with thought leaders, rather than just hiring any type of influencer. We're finding people that really use ClickUp that also have a reach and then having them share ClickUp in more creative ways. We're not just saying: “Hey, you should try out ClickUp, it's a cool platform.” What we're doing is saying: “Hey, I know that you're a marketer. Here's a doc that we built for you that'll help you. Here's 165 marketing prompts that will help in a ClickUp doc." Our marketing is all value-based. It isn't in your face telling you to use our product, our marketing is helping your day-to-day. That's what we see as the future of marketing.
You tweeted something along the lines of "Don't sell the product, sell the transformation." Could you elaborate on what you mean by that?
One of my favorite things to think about is that everyone just sells their product. But the real thing that I want to provide, and that I'm working to do, is showing how our customers use ClickUp. "Here was our customer before they used ClickUp. Here they are now. This is a transformation that you can have." I'm going to show you how these features made their life is easier now and backing up this bold statement of saving a day a week. Here's how. They're saving time because we have these automations, plugins, and because we have customer service that will take its time to help you with your workflow. We'll give you consultants to work with you and dive in fully.
The real key isdon't just talk about your brand and your features, don't just throw that out. People can look it up on their own. What they can't find is how you've helped others, how you've saved them time, how you've made them more money, and how you've made their lives easier.
If we look back at your career so far, even with some of the things that you're doing now, it's clear that you are absolutely not afraid of taking risks. What makes you feel ready to take those leaps, and how do you know it's the right time to take them?
I don't know if I've actually thought about it. I realized that a lot of times the failure that you're afraid of doesn't come like you think it will. We failed with an app called Memory. We went all in, spent a lot of money, and we failed. Of course, there's a hit to your pride and ego when you tell everyone “Hey, we're going to be the next big social media app”. And you're not. But you also learn so much during that time. I think I lost the fear of failure first. I'm not afraid to fail. As you do fail, you start recognizing timing. Sure, I'd have loved to have dropped the ClickUp album a while ago, but I was smart about when to do it. I think the timing was right with our conference and with what we were doing.
I also find ways to take these risks in ways that have low repercussions if they fail. I didn't spend a ton of money on the album. If no one listened to the album, that's okay. Even if there were only 20 streams, I still have assets that I can use for our marketing that I don't have to go pay for and that are cool songs. I still have something that you can tag on Instagram or on TikTok and use as a sound. These are still assets for me. I learned how to mitigate the risk as well. I think that's something else you learn as you go through your career.
The three things are mitigate the risk if you can. But again, you can't be afraid. And be very good at timing. Look at all the other factors. Look at how you can amplify it by other things you're doing.
