ClickUp’s Social Media Playbook: Entertain First, Sell Later

Apr 16, 2026 · Exit Five
🎧 PodShort 31 min squeezed to 2 AI SprinklerAS Sales Tech
Episode artwork
Chris Cunningham
Founding Member of the Marketing Team at ClickUp
Exit Five
31 min squeezed to 2
Full episode from Exit Five
Quotable Moments

99% of companies are just talking about their product on social, that's the wrong thing. When people pull out their phone, they want to laugh, they want to feel something, they want to learn.

Chris CunninghamFounding Member of the Marketing Team at ClickUp
03:50

I've got actors twerking in videos, right? Like what other company can I go to that'll let me do that? Now, maybe since I've proven it, yes, but like only at ClickUp could I try and have this free rein.

Chris CunninghamFounding Member of the Marketing Team at ClickUp
04:30

There's something funny in no matter what space you're in. If it's you put me, you today, you drop me in a new space, guarantee I can make funny content for doctors, guarantee I can make funny content for lawyers. You know why, Dave? Because my formula is this: I really know my ICP.

Chris CunninghamFounding Member of the Marketing Team at ClickUp
10:00
Key Insights
  • Most B2B companies treat social media as a platform for more ads, which is a mistake because people use social media to be entertained, learn, or feel something, not to be sold to.
  • To succeed on social media, content needs to either make people feel something, add value, or teach them something. If it doesn't meet one of these criteria, it shouldn't be posted.
  • Companies should be present on every social media platform but only create content specifically for a select few, then distribute that content across all channels.
  • A/B testing every video, even with small audiences, is crucial because the best-performing version is often not the one initially thought to be superior, leading to significantly higher engagement.
  • The key to creating engaging social media content is to deeply understand your Ideal Customer Profile (ICP) by actively engaging with them, such as through 'reverse interviews,' to discover what resonates and what they find funny.
  • Social media can drive significant pipeline and revenue, even if direct attribution is challenging. Early signals include increased inbound applications for HR and direct mentions from sales prospects about discovering the company through social content.
  • There is a sweet spot for content volume on social media; posting too frequently can actually decrease engagement and reach, as observed when doubling posts led to a noticeable decline in numbers.
  • AI-generated content does not resonate as strongly with human audiences as content created by other humans, because people crave genuine connection and authenticity, making human creativity a significant competitive advantage.
Metrics Mentioned
  • 30 million impressions (Achieved in a month on social media after starting with a small team.)
  • 100 million impressions (Target set by the CEO after reaching 30 million impressions.)
  • 100 million views (Achieved from Facebook Reels, highlighting its significant reach.)
  • 300 million (The amount TPN was bought for, illustrating the value of content platforms.)

RevBots.ai View:

  • AI Sprinkler teams often bolt on AI tools for content creation but miss the mark on authenticity.
  • ARM-stage companies would integrate social insights into broader AI-driven GTM orchestration.
  • Tab Hopper and SaaS Hoarder teams struggle with operationalizing high-volume content creation.
  • Social media success requires a shift from product-centric to ICP-centric storytelling.
🎧Full Episode:Exit Five →