ClickUp's Head of Social Reveals the Secret to 200M+ Monthly Views

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 episode of Uploading, Chris shares lessons learned from scrappy beginnings to leading a viral content machine, the key bets and breakthroughs along the way, and actionable advice for creators and brands looking to scale content that actually moves the needle.

Fav Quotes From Episode #31

“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

3 Strategies for Success From Chris Cunningham

1. Build your content engine like a TV show

Think your B2B brand is too “boring” to go viral? Chris Cunningham’s playbook at ClickUp proves otherwise. One of his game-changing strategies is to treat content creation like running a TV show: every week, there’s a writer’s room, a slate of new ideas, a production schedule, and a team that’s constantly iterating.

Here’s how Chris pulls it off:

• Weekly writer’s rooms: Every Monday, the team gathers to brainstorm and pitch nine or more video concepts, just like a comedy show’s writers would.

• Punch-up, refine, and prep: On Tuesday, the team chooses the winning ideas and refines scripts, ensuring that only the strongest—and most shareable—survive.

• Batch production: Thursdays are for shooting. Dedicated creators spend the whole day filming, ensuring there’s a steady pipeline of content to test and publish.

What does this look like in action? Relatable “HR guys” skits, trending audio rewrites, and rapid engagement with business culture moments—all created with a repeatable, collaborative system.

To get started, gather your marketing team (or just your most creative colleagues!) and block off time to brainstorm together. Build a lightweight weekly workflow for ideas, refinement, and production—even if you’re just working with a smartphone and a couple of enthusiastic teammates. Consistency and collaboration are what drive the content machine forward.

2. Bet small, iterate fast, and double down on winners

Forget “big bang” campaigns that drain your budget with no guarantees. Chris’s take: treat every new content idea as a bet—start small, launch quickly, and let data decide what gets more investment.

Here’s how ClickUp’s betting system works:

• Low-budget, high-frequency experimentation: Launch content ideas with minimal costs, whether it’s a new video series or a trending format.

• Face quick feedback head-on: Track performance within six to eight weeks. If a piece starts to outperform—say, nabbing millions of views—secure more resources and scale up.

• Repeat successful “shots on goal”: Chris’s team doesn’t shy away from remixing and repeating formats that are proven hits (like their HR dance sketches), adapting cadence to avoid audience fatigue.

In your own practice, this means keeping content costs flexible, launching ideas often, and doubling down only when something clearly resonates. It’s a process rooted in rapid testing rather than guesswork or arbitrary deadlines.

Use simple analytics to monitor what’s working, and don’t be afraid to quietly retire ideas that don’t deliver. Over time, you’ll create a content ecosystem that feels both experimental and measurable—and far more sustainable.

3. Connect content to the entire grown funnel

It’s easy to get caught up in making funny or viral videos and forget about business impact. Chris’s secret is integrating every piece of content into ClickUp’s full growth funnel—moving audiences from broad awareness all the way to demo bookings and closed deals.

Here’s how ClickUp does it:

• Entertain to attract: Viral skits and relatable workplace content open the door, driving massive top-of-funnel impressions from wide audiences.

• Retarget and educate: Anyone who engages with entertaining content is later retargeted with product-focused videos (often starring the same beloved characters), seamlessly introducing ClickUp’s capabilities.

• Personalize and close: For high-value leads or deals in progress, the team crafts bespoke videos—sometimes even personalized messages from the “HR guys”—to delight prospects and nudge them toward conversion.

Chris also pulls in data from their AI tools to identify who’s following the brand, seizing opportunities for hyper-targeted outreach.

To make this work for your brand, plan your content with multiple stages in mind: what will grab attention (top of funnel), what will nurture interest (middle), and what will help close sales (bottom). Align metrics to each step and create clear handoffs from fun, shareable moments to practical product stories.

By weaving entertainment and education together—and keeping everything tied to concrete business goals—you’ll ensure your content engine doesn’t just go viral, but drives real growth.

We're excited to be part of your journey to turn content into business.

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