How ClickUp Built a B2B Social Machine with Chris Cunningham from ClickUp

24 snips

Apr 16, 2026

Chris Cunningham, a founding member of ClickUp's marketing team who leads their social strategy and comedy-driven content. He explains why most B2B social is wrong. He breaks down the weekly writers room and shoot day that pumps out 12–15 videos. He shares how ClickUp tests hooks, runs 35 accounts, finds unknown creators, and why human creativity is the biggest moat against AI.

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ADVICE

Always Test Multiple Hooks With Trial Reels

Always A/B test hooks by posting multiple edits into Instagram Trial Reels before the main feed.
Chris runs three edits of every video with different on-screen text/hooks and uses Trial Reels to discover which explodes (millions vs thousands of views).

ANECDOTE

Viral Social Content Helped Close Big Agency Deals

ClickUp closed major deals (e.g., VaynerMedia) that cited social as the discovery channel.
Chris credits social virality and recognizable actors leading prospects to give ClickUp a chance and ultimately win business.

ADVICE

Interview ICPs Regularly To Mine Authentic Ideas

Interview your ICP 20–30 times to source real ideas and comedic beats; record calls and give participants clips as a gift.
Chris cold-LinkedIns ICPs and customers for 15-minute Riverside interviews and uses their stories as content fuel.

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#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 distribute everywhere
(11:34) - - How ClickUp separates brand, comedy, and product accounts
(13:41) - - How social has driven real pipeline and closed deals
(16:01) - - How Chris interviews ICPs to find content ideas
(20:02) - - How to measure social when attribution is hard
(25:08) - - The weekly production process: writers room, shoot day, and content bank
(32:00) - - Tools and how to manage posting across 35 accounts
(33:34) - - Don't sleep on Facebook Reels
(35:06) - - How to start if you're camera shy and how to find unknown creators
(40:48) - - Where AI fits in and why doubling down on human creativity is the biggest moat
(45:32) - - Why brand is now the biggest competitive advantage in B2B
(47:39) - - Unique content formats worth studying and stealing

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