Uploading

About the Episode: Chris Cunningham is a founding member and Head of Social Marketing at ClickUp, the fast-growing productivity platform now valued at $4 billion. Since shaping ClickUp’s brand voice and social presence from 2017, Chris has been instrumental in engineering a content system that regularly generates 200M+ monthly impressions and consistently translates content virality into real leads and customers. In this workshop episode of Uploading, Chris breaks down ClickUp’s journey from early hustle—making videos solo and closing deals by hand—to building a repeatable, scalable content operation with an in-house “writer’s room,” comedic actors, and a growth strategy spanning multiple platforms. Chris and host Blaine unpack content pivots, hiring creators, building brand voice, and why entertainment-first content matters for B2B. Chris also gets tactical: how to mix content types across the funnel, the operational playbook for consistent output, leveraging AI tools, success metrics, and what it takes to hit massive growth milestones. Finally, Chris shares actionable frameworks for solo founders and small teams starting from scratch—plus candid takes on virality, team structure, platform strategy, and what’s next for ClickUp’s $4B content engine. Today, we'll cover: - How ClickUp scaled from low-budget solo content to 200M+ impressions per month - The “bets” and breakthroughs that defined ClickUp’s content playbook - Building a repeatable system: team, workflow, “writer’s room,” and actors - Entertainment vs. product-driven content—and the ideal content mix - Measuring ROI: turning impressions and brand awareness into real leads and customers - Frameworks and advice for solo creators and early-stage teams to start content from scratch - Platform-specific strategies for LinkedIn, Instagram, TikTok, YouTube, and beyond - Personalization, AI, and creator partnerships: the new wave of B2B content What You'll Learn 1. Building a Scalable Content Engine 2. Hiring and Leveraging In-house Creators 3. Mixing Entertainment and Product Content 4. Omnipresence across Multiple Social Platforms 5. Testing, Iterating, and Doubling Down on Winners 6. Aligning Content with Business Goals and Funnels 7. Creating Efficient, Repeatable Content Systems Timestamps 00:00 Meet Chris Cunningham: ClickUp’s content architect 02:11 Chris’s background: from agency to ClickUp’s founding team 08:07 Platform-specific content strategy & goals 11:28 Making content a team priority: systems & scheduling 14:37 Inside ClickUp’s instagram strategy 15:38 The ABCD formula: testing for virality 16:09 Case study: viral skits, trends, & relatable office content 19:29 Operations: writers’ room, shooting schedule, & execution 23:23 Starting from scratch: building in public & early tactics 25:47 Frameworks for virality: the anatomy of a viral video 27:41 Winning concepts: relatability, shareability, & emotional triggers 30:55 Scheduling vs manual posting: what works best 32:18 YouTube strategy: current state & future focus 33:36 Platform prioritization: focus, layering, & growth sequence 35:52 Content funnel mix: brand awareness vs product promotion 37:24 Content ratio: top, middle, & bottom of funnel by stage 40:00 Staff vs. actors: who should be in your content? 42:10 Video length: short vs long content & platform preferences 43:35 Looking ahead: 2025 content experiments & new channels 46:19 Where to follow Chris & ClickUp “We’ve very big on shots on goal. We want to put as many shots up as possible, but we want to have calculated shots. We want to take them with low budgets… I’ll make a bet and I’ll start it very cheaply.” — Chris Cunningham “The only way it’s really going to scale is if I brought in an expert... I took a bet that all companies would have content creators if they wanted to compete. They’ll have some kind of creator that creates content for them consistently.” — Chris Cunningham “Content's just another task, right? Like anyone can make excuses. So if you're just not making content, it means you don't prioritize it. We prioritize it.” — Chris Cunningham “The dividends content rewards with is nuts. The amount of people I’ve met, the people who DM me and just what I’m learning… There’s no reason not to make content.” — Chris Cunningham “If I had to start over and I’m at a new company—we’re building in public... No actors, just talking about what we’re working on. At the end of the day, I would just ask for like 5-10 minutes of all the early employees: what did you do today? And find a cool, clever way to chop it up. That’s exactly what I would do.” — Chris Cunningham “You need to know your ICP. If you’re creating content and you don’t know who you’re creating for, you really just lost the whole goal right there.” — Chris Cunningham Show notes powered by Castmagic --- Have any questions about the show or topics you'd like us to explore further? Shoot us a DM; we'd love to hear from you. Want the weekly TL;DR of tips delivered to your mailbox? Check out our newsletter here. Follow us for content, clips, giveaways, & updates! Castmagic Instagram Castmagic Twitter Castmagic LinkedIn   --- Blaine Bolus - Co-Founder of Castmagic Ramon Berrios - Co-Founder of Castmagic Chris Cunningham - Head of Social Marketing at ClickUp