How ClickUp Built a B2B Social Machine with Chris Cunningham from ClickUp
The Dave Gerhardt Show · 2026-04-16 · 50 min
Episode notes
#347 | ClickUp drives millions of impressions for the company through videos and content for B2B marketers on social, and in this episode Dave sits down with Chris Cunningham , a founding member of the marketing team at ClickUp and the guy who runs social there now, to talk about how they do it. Chris breaks down why 99% of companies are doing social wrong, how ClickUp runs a weekly writers room and shoots 12 to 15 videos every Thursday, and why he tests every video with multiple hooks using Instagram trial reels before it ever hits the main feed. He also gets into how he manages 35 accounts across platforms, how he finds unknown creators with small followings and turns them into writers, and how this has driven real pipeline. Then the conversation shifts to AI and whether doubling down on human creativity might actually be B2B's biggest competitive advantage right now.
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