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How ClickUp Became the SNL of Project Management Platforms
Meet Chris Cunningham, the Lorne Michaels of workplace humor
Chris Cunningham, head of social marketing at project management software provider ClickUp, looks forward to Mondays. That’s the day the ClickUp writers room typically meets. And he loves gathering with colleagues to brainstorm ideas for the corporate comedy videos the company has become known for producing and sharing on social media.
You’ve likely seen them on TikTok, Instagram, Facebook or LinkedIn.
Luke, aka blue shirt guy, and Adam, who tends to wear a black shirt, are the stars of the clips. They poke fun at corporate jargon, employees singing and dancing during presentations and other workplace silliness.
Cunningham cites The Office and Step Brothers as some of his favorite comedies, and you can see the influence of both in the steady stream of videos ClickUp produces. “The goal is to try to make 10 videos a week, maybe one or two being an ad” for specific ClickUp services, Cunningham says. “We tried pushing for more, but I think that lowers the quality. So that’s kind of the sweet spot we’re at now.”
Cunningham’s writers room includes Marc Stone (also ClickUp’s head of content growth); actors Luke Kostas and Adam Young; and social media manager Stormie Kadar. “Every now and again, just to freshen up and bring in new ideas, I might go hire a writer,” Cunningham says.
And much like a TV show writers room, “We all come prepared with ideas. We all pitch. There’s no ego,” he says. “At the end, we vote blindly, and whatever videos ideas win, those are the ones we shoot. Then we’re editing and posting through the next week, and then we just kind of keep that machine going.”
The low-budget vids, shot on an iPhone in ClickUp’s San Diego, are getting tons of impressions—150 to 180 million every month.
“Some would ask, ‘Does that drive leads?’ It definitely does,” Cunningham says. “But our goal is for people to know about us. Because at the end of the day, people are going to shop for project management when they want to shop. So, our goal is that we are in the mix, for more people to hear about ClickUp and check it out. We’re serving as an additional billboard.”
While the comedy videos have become a valuable marketing tool, making them seemed risky at the start. But like any committed creative, Cunningham lobbied for his vision. “Some people were like, ‘This is weird. This doesn’t make sense.’ But I was like, “Please trust me.'”
And they did.
“I cannot believe I manifested this as being my job. I absolutely love it,” Cunningham reflects, noting that projects like this “open doors for other people to take a little more risk and have some fun in the B2B space.”
