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

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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.

Episode 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