Unpacking the Social Media Playbook of a $4B brand | Chris Cunningham (ClickUp)

Jul 15, 2025

Chris Cunningham, a founding member of ClickUp, shares his expertise in crafting a social media strategy that garners an impressive 150 million monthly impressions. He reveals the power of humor in B2B marketing and discusses innovative hiring practices, like recruiting LA actors for content creation. Chris introduces his unique Trial Reels technique for testing content effectiveness and shares insights on balancing entertainment with product promotions, ultimately breaking conventional marketing norms to create engaging and relatable brand content.

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ADVICE

Measure Social With Dedicated Landing Pages

Track social-driven signups by linking profile CTAs to custom landing pages and measuring demos and conversions.
Use self-attribution surveys and bio links to estimate ROI when exact dollars are hard to pin down.

ADVICE

Scale Budget Only After Proof

Start small and scale budget after signal: test with scrappy shoots before adding actors and production spend.
Give experiments time (Chris got board buy-in after ~3 months of breakout videos) and expand when metrics improve.

ADVICE

Hire Hungry Actors Near Talent Pools

Hire actors and writers from talent hubs (LA improv, Groundlings) and offer steady pay to attract quality performers.
Train them in the product and office culture so they can authentically translate business jokes and scenarios.

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