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

#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 (02:10) - - Chris's background and why he's been at ClickUp for nearly a decade (04:06) - - The biggest mistake B2B companies make on social (06:14) - - The rule of three: make people feel something, teach them, or make them laugh (07:25) - - Why you should create for two platforms and distribute everywhere (09:19) - - How ClickUp separates brand, comedy, and product accounts (11:26) - - How social has driven real pipeline and closed deals (13:46) - - How Chris interviews ICPs to find content ideas (17:47) - - How to measure social when attribution is hard (22:53) - - The weekly production process: writers room, shoot day, and content bank (28:40) - - Tools and how to manage posting across 35 accounts (30:14) - - Don't sleep on Facebook Reels (31:46) - - How to start if you're camera shy and how to find unknown creators (37:28) - - Where AI fits in and why doubling down on human creativity is the biggest moat (42:12) - - Why brand is now the biggest competitive advantage in B2B (44:19) - - Unique content formats worth studying and stealing Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more