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 building an in-house content engine that moves the needle. From hiring actors full-time, to turning their content meetings into writers’ rooms, to making rap albums that actually convert.

We talk about:

• The content framework that helps their team test and scale what really works
• Why they bet on humor at the top of the funnel—and what makes it land
• How they avoid burnout while making videos every week
• The limits of AI content (and why originality still matters most)
• What most B2B teams get wrong when they try to “act like media companies”