How ClickUp Built a B2B Social Machine with Chris Cunningham from ClickUp
From The Dave Gerhardt Show (from Exit Five) by Exit Five
April 16, 2026 · 54 min · Episode 347
About this episode
In this episode, Chris Cunningham from ClickUp discusses their innovative B2B social media strategies and the importance of creativity in marketing.
#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. Timestamps (00:00) - - Intro (04:25) - - Chris's background and why he's been at ClickUp for nearly a decade (06:21) - - The biggest mistake B2B companies make on social (08:29) - - The rule of three: make people feel something, teach them, or make them laugh (09:40) - - Why you should create for two platforms and…
People in this episode
Host: Dave Gerhardt
Guest: Chris Cunningham
Topics covered
- B2B marketing
- social media strategy
- content creation
- video marketing
- AI in marketing
Keywords
- ClickUp
- B2B marketing
- social media
- content strategy
- video production
- AI
- creativity
Mentioned in this episode
Organizations: ClickUp
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