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How to Turn Marketing into Entertainment with Chris Cunningham of ClickUp

Everyone’s chasing AI—but what if the real magic in B2B is a rap video, a meme, and two actors with a camera?

While most brands stick to safe, polished playbooks, Chris Cunningham is building ClickUp’s marketing like it’s a full-blown media company—and it’s working. In this episode, he takes us behind the scenes of how their small but mighty team racked up 200 million+ impressions by leaning into creativity, comedy, and community.

Chris, one of ClickUp’s original team members and now Head of Brand, shares the real (and often hilarious) story of how they went from startup scrappiness to…

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