Uploading... - The Playbook Behind ClickUp’s $4B Content Engine

Castmagic LinkedIn Post

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Turning your content into serious business growth? That’s what every creator, founder, and marketer wants—but few master. ClickUp’s Head of Social Marketing, Chris Cunningham, joins Blaine on Uploading to unpack the content engine behind ClickUp’s $4B brand. Chris helped scale ClickUp from startup to a SaaS powerhouse pulling in over 200 million+ monthly impressions and building some of the most viral B2B content on the internet. In this episode, we dig into how ClickUp’s content strategy started small and went viral, the systems and team culture powering consistent output, keys to measuring and monetizing content, and top advice for anyone looking to scale their brand with repeatable, high-impact content. Full episode here: [link] #contentstrategy #saasgrowth #branding #b2bmarketing #uploadingpodcast

3 quick tips

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99% of brands struggle to get attention with their content. Here are 3 proven strategies from ClickUp’s $4B content engine👇 1. Test Relentlessly In ClickUp’s early days, it was all about “shots on goal.” Try 40+ pieces. Test different styles and concepts: • Short skits • Music parodies • Trending memes • Thought leadership posts After testing? Double down on what pops off. 2. Mix your content types Don’t just chase virality. The best brands blend: • Entertaining, viral videos (to get attention) • Product walk-throughs (to educate) • Insightful carousels (to build authority) • Relatable skits (to boost shares) Your ratio should adapt as you grow. Early days? More product. At scale? More brand. 3. Build a content assembly line Don’t do it all yourself. ClickUp’s playbook: 1) Host a “writer’s room” every Monday for ideas 2) Pick the best scripts Tuesday 3) Shoot every Thursday 4) Hire (or contract) creators, not just employees Consistency > Perfection. Volume + iteration = Outlier results. Bonus: Block time for content creation—schedule it just like any other meeting. The $4B takeaway: Treat content like a product. Test, iterate, and build a repeatable engine. Steal these frameworks, and watch the impressions roll in.

📚 Timestamped overview

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00:00 Scaling ClickUp's Viral Content Strategy

04:14 "Content-Driven Sales Transformation"

07:21 ClickUp's Messaging Strategy With Creators

09:53 "Effective Marketing & Sales Strategy"

13:16 "Consistency in Content Creation"

19:29 Executing Creative Video Concepts

22:34 Starting a Brand from Scratch

24:42 "Formula for Going Viral"

28:29 Audience-Centric Content Creation Strategy

32:18 YouTube Growth Strategy Discussion

35:10 Content Strategy: Virality vs. Intent

38:46 Brand vs. Performance Marketing Strategies

42:37 Optimize Video Length Strategically

43:06 Optimizing Video Length Strategically

46:34 Contact Chris for Social Consulting

🎞️ Clipfinder: Quotes, Hooks, & Timestamps

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Chris Cunningham 00:05:41 00:05:47

The Future of Content Creation in Companies: "I took a bet that I thought all companies were going to have content creators if they wanted to be, you know, to really compete in this game."

Chris Cunningham 00:08:35 00:08:36

Viral Topic: Do Funny TikToks Actually Bring Leads?

"It definitely does."

Chris Cunningham 00:08:57 00:09:04

Viral Marketing Strategy Revealed: "But we'll find you later, we can retarget you, right? So now my CAC payback is lower because I'm running an ad with two characters you've already seen, you're much more likely to watch."

Chris Cunningham 00:10:17 00:10:29

Personalized Sales Tactics That Win Deals: "what I'll do is I'll, I'll have them on their next shoot make a personalized video for them. Something easy, something low effort, but it shows we took the time to research who they are or if there's a champion on a deal that's close to closing, the deal is already closed, anything like that."

Chris Cunningham 00:24:42 00:24:42

Building in Public on LinkedIn: "I would just start building it public. People love it, especially on LinkedIn and LinkedIn is a powerful place you can start."

Chris Cunningham 00:29:43 00:29:47

Viral Topic: The Importance of Knowing Your Audience
Quote: "if you're creating content, you don't know who you're creating for. You really just kind of Lost the whole goal right there."

Chris Cunningham 00:36:56 00:37:03

Becoming a Thought Leader with Impactful Content: "I think just like actually like putting content out there that makes people better at their job, I think is the only other one that I would create."

Chris Cunningham 00:37:35 00:37:47

Why People Really Scroll Social Media: "When you pull out your phone and you pull out Instagram, you pull out X. Like are you looking for, to be sold to, you know, and told about your brand? Most of the time not. There is definitely times where I want to, most of I just want to take a break."

Chris Cunningham 00:40:27 00:40:40

The Rise of In-House Content Teams: "Well, I've got two, two full, like literally two, two people are paid full time and this is what they do. They create, they create content. Right now they have certain goals. They need to create seven, you know, videos we post short for a week and they need to create like 1, 2 ads a week."

Chris Cunningham 00:42:43 00:42:53

Viral Video Length Debate: "There's some videos like my, like that one, if you watch this kind of recent where they're doing the it, that's maybe like 18 seconds, right, that hit because it's like you almost want to watch it again."

ℹ️ Introduction

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Welcome to another episode of *Uploading...*, where we dive into the biggest strategies behind today’s most impactful content engines. In this episode, your host Blaine is joined by Chris Cunningham, a founding member and Head of Social Marketing at ClickUp—the AI-powered productivity platform valued at over $4 billion. Chris takes us behind the scenes of ClickUp’s explosive content growth, revealing how a small, scrappy team grew into a viral B2B SaaS brand, generating over a billion impressions in 2024 alone. We’ll break down the pivotal moments that shaped ClickUp’s approach, from the earliest experiments to the decision to build an in-house creator team. Chris shares the repeatable systems, creativity-improving rituals, and strategies that helped ClickUp balance entertainment with brand messaging—all while driving real business results. Whether you’re a solo creator, part of a marketing team, or building your brand from scratch, this episode is packed with actionable advice on scaling content, measuring success, and staying ahead of the curve in today’s social media landscape. And don’t miss out—Blaine also announces the launch of a brand new, vetted Uploading community to help you connect with top creators and scale your own journey. Let’s dive in and discover how ClickUp turned their content playbook into a $4 billion engine.

💡 Speaker bios

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Chris Cunningham is a seasoned entrepreneur and one of the original four founders of ClickUp. His journey into the world of startups began in Charlotte, North Carolina, where he and his close-knit team launched an agency that quickly found success. Fueled by their early achievements and a drive to tackle more ambitious projects, Chris and his crew set out to develop a new social media app called Memory. The inspiration for Memory came from a desire to improve upon Snapchat; while Snapchat erased users’ memories after just seven seconds, Chris’s team wanted to create a platform where moments could be preserved and revisited. Memory gained traction, proving the team’s knack for identifying gaps in the market and developing innovative solutions. Building on the lessons learned from their previous ventures, Chris and his co-founders eventually turned their attention toward an even greater challenge: reinventing productivity and workspace tools. This vision led to the creation of ClickUp, a platform that has since transformed how teams collaborate and manage work. From agency beginnings to cutting-edge SaaS, Chris’s story is a testament to bold thinking, adaptability, and relentless pursuit of bigger opportunities.

💬 Keywords

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Sure! Here are 30 topical keywords that were covered in the transcript: personal brand, private community, content creators, B2B SaaS, ClickUp, social marketing, AI productivity platform, impressions, viral content, content strategy, content systems, team culture, content measurement, content monetization, Super Bowl ad, inbound leads, outbound sales, content creators hiring, writers room, vetting process, omnipresence, product marketing, thought leadership, LinkedIn content, TikTok, Instagram, YouTube, content funnel, brand awareness, top of funnel content

❇️ Key topics and bullets

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Absolutely! Here is a comprehensive sequence of topics covered in the transcript, with sub-topic bullet points under each main topic: --- **1. Introduction and Community Announcement** - Announcement of the new, private Uploading community for content creators and personal brand builders - Details on community access, vetting process, and value for serious creators **2. Meet the Guest: Chris Cunningham and His Role at ClickUp** - Chris’s background and entrepreneurial journey before ClickUp - Founding ClickUp and the transition from sales to social marketing - Early experiences as a first sales rep, customer support, and marketer - ClickUp’s evolution into a $4B AI-powered productivity platform **3. Origins of ClickUp’s Content Strategy** - Starting lean with low-budget, experimental "shots on goal" - Chris’s initial content formats (e.g., videos, raps) - First major pivot: hiring an expert content creator (Luke) and scaling up - Importance of measurable bets and incremental investment in content **4. Growth and Systemization of the Content Engine** - Building a repeatable content system: daily shooting and content iteration - Hiring and working with internal content creators and actors - Creating a “writer's room” structure with ideation, pitching, and production **5. Content Strategy and Platform-Specific Approaches** - Tailoring content to each platform (LinkedIn, Instagram, TikTok, X/Twitter, YouTube) - Entertaining, top-of-funnel content vs. product-driven, educational, or bottom-of-funnel content - Using humor, relatability, and trends—balancing product demo content with entertainment **6. Integrating Content into the Growth Funnel** - Role of content in driving brand awareness, lead generation, and sales - Retargeting strategies using familiar on-screen personalities - Use of QR codes and personalized content for sales enablement - Case study of closing major deals through social media discovery **7. Operations: Workflow and Team Collaboration** - Scheduling, batching, and prioritizing content creation - Leveraging AI tools (like Claude) for repurposing, scripting, and editing - Importance of prioritization and consistency in personal and brand content **8. Content Formats and Examples** - Breakdown and live show-and-tell of ClickUp’s Instagram and LinkedIn feeds - Use of repeatable formulas (e.g., HR skits, trending formats, man-on-the-street) - Experimentation and analysis of content performance by channel **9. Executing at Scale: Building a Content Team** - The structure, roles, and processes: in-house creators, actors, editors - Balancing in-house staff appearances vs. dedicated creative talent - Use of office employees and occasional contract actors **10. Recommendations for Small Teams and Solopreneurs** - Building in public and documenting the entrepreneurial journey - Leveraging early team members and hiring emerging creators - Testing, iterating, and optimizing content with limited resources **11. The "Viral Formula": Ideation and Measurement** - Elements that contribute to virality: relatability, nostalgia, shareability - Framework for brainstorming and producing share-worthy content - Importance of knowing and targeting your ICP (ideal customer profile) **12. Platform-Specific Best Practices** - Manual vs. scheduled posting and its impact on performance - Analytics, engagement groups, and the pros/cons of shortcuts - Choosing the right mix of channels for your content strategy **13. Content Mix and Funnel Ratios** - Recommended mix for entertainment, product, and thought leadership content - Adjusting content ratios based on business stage and objectives **14. Future Trends and Expansion Plans** - Moving toward YouTube/long-form episodic content as next frontier - Experimenting with new platforms, formats, and micro-influencer strategies - Continual testing of new approaches to hit ever-increasing impression goals **15. Audience Q&A** - Content buckets: virality vs. intent-based content - Ratio and strategic mix of content types - Thoughts on engagement pods and platform specifics on scheduling - Video length, format testing, and cross-platform adaptation **16. Closing Remarks** - Where to follow Chris and ClickUp online - Offer for consulting/support and encouragement to content creators --- Let me know if you’d like this sequence refined further, specific timestamp breakdowns, or deeper dives into any section!

🎠 Social Carousel

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**10 Tips Every Content Marketer Needs to Know** Swipe ➡️ for ClickUp’s secrets to building a $4B content engine --- **1. Take Shots** Test many content ideas (shots on goal) cheaply and quickly. Double down on what actually performs. --- **2. Start Scrappy** In the beginning, do it all yourself—film, edit, and experiment before bringing on experts or big budgets. --- **3. Hire Creators** Invest in real content creators, not just internal employees. They elevate quality and consistency. --- **4. Make it Relatable** Create funny, shareable content that connects emotionally—or nostalgically—with your ideal audience. --- **5. Platform-Specific** Tailor your content style to each platform—what works on TikTok won’t always work on LinkedIn. --- **6. Mix the Funnel** Balance top-of-funnel entertainment with educational and product-driven posts for conversion. --- **7. Iterate Ruthlessly** Review data, remix what works, cut what doesn’t, and keep your ideas fresh weekly. --- **8. Batch & Block** Batch-shoot content once a week, then edit and schedule—you don’t need to film daily to stay consistent. --- **9. Go Human, Not Just AI** AI can support, but human ideas drive real virality—especially for humor and trends. --- **10. Build in Public** Share wins and struggles transparently—building in public makes your audience invested. --- **Ready to level up your brand’s content?** 👉 Join our free community or DM for more content growth tips! #UploadingPod

❓ Questions

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Absolutely! Here are 10 discussion questions based on this episode of "Uploading...," featuring Chris Cunningham from ClickUp: 1. **Chris talked about the “shots on goal” mentality. How do you balance taking lots of creative risks with being intentional about budget and resources when building a content engine?** 2. **The ClickUp team made an early bet on hiring full-time content creators and even actors. What are the pros and cons of investing in dedicated talent for your content versus relying on existing team members?** 3. **ClickUp’s content strategy shifted from founder-led videos to a ‘writer’s room’ approach. How might this collaborative model change the quality or diversity of content a brand produces?** 4. **Chris mentioned separating content by platform, with more thought leadership on LinkedIn versus entertainment skits on Instagram and TikTok. What are some ways to tailor content to different platform audiences without losing brand consistency?** 5. **Measurement and ROI came up frequently—what are some creative ways to directly connect top-of-funnel content (like funny videos) to actual business metrics and leads?** 6. **How important is it for founders and leaders to be part of the content creation process, and how can you encourage participation across your team without it feeling forced or overwhelming?** 7. **The episode highlighted the value of building in public, especially for startups. What does ‘building in public’ look like in practice and what risks or rewards come with this approach?** 8. **Chris described going viral as almost formulaic, emphasizing relatability, shareability, and targeting ICP (ideal customer profile). Do you agree there’s a repeatable formula to virality? Why or why not?** 9. **The team experiments with video length, trends, and formats—from music parodies to man-on-the-street interviews. How do you decide when to double down on a successful format versus pivot to something new?** 10. **As ClickUp scales and approaches broader goals (like 300 million monthly impressions), Chris discussed iterating on both content and channels. What challenges arise when trying to scale content volume and quality simultaneously, and how do you avoid burnout or creative stagnation?** Feel free to use these to spark conversation in your group, classroom, or team meeting!

🎬 Reel script

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Just wrapped an amazing session with Chris Cunningham, the mastermind behind ClickUp's $4B content engine. We broke down exactly how ClickUp went from scrappy beginnings to a viral B2B content powerhouse pulling in over a billion impressions this year. Chris shared real, actionable insights on hiring creators, building repeatable systems, and mixing viral entertainment with product-driven content to drive serious business results. If you’re serious about scaling your content and turning views into value, you’ve got to check out Chris’s playbook. Follow for more content growth strategies!

🔑 7 Key Themes

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Absolutely! Here are 7 key themes from the episode: 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

💎 Maxims

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Absolutely! Drawing from the wisdom and strategies shared in the podcast episode “The Playbook Behind ClickUp’s $4B Content Engine,” here are some maxims to live by for anyone building a content-driven brand, business, or personal mission: ### Content, Creativity, and Consistency 1. **Block Out Time—Don’t Make Excuses:** If you’re not creating content, you’re just not prioritizing it. Schedule your creative time like any other meeting or task. 2. **Consistency Compounds:** Small, repeated actions (like weekly content sprints) build momentum and drive exponential results over time. 3. **Just Start—Don’t Overthink Early Days:** In the beginning, quantity and testing matter more than perfection. Don’t let overplanning stall you. 4. **Treat Content as a Task, Not an Afterthought:** Make content creation a core part of your workflow, not something you’ll “get to later.” 5. **Iterate, Test, Repeat:** The path to virality or effectiveness runs through relentless experimentation and iteration. What works gets doubled down. ### Teamwork & Talent 6. **Surround Yourself with Experts:** Don’t be afraid to bring in or collaborate with creators who are better at content than you are. 7. **Build a Creative “Writer’s Room” Culture:** Regular brainstorms, open pitching, and collaborative punch-ups lead to better ideas and stronger execution. 8. **Empower People to Do What They Do Best:** Hire for specific creative or content skills rather than burdening reluctant employees with extra tasks. ### Strategy & Brand 9. **Play the Omni-Platform Game:** Be where your audience is, but start with one or two key channels and expand as you master new platforms. 10. **Shoot Calculated, Low-Budget Shots on Goal:** Take lots of “bets” or experiments, but manage risk with lean, creative approaches. 11. **Let Your Brand’s Voice Evolve:** Start simple but continually refine your message, style, and platform mix as you grow. ### Measuring Value 12. **Track What Matters—Especially Shares:** Shares are a deeper indicator of impact than likes. Optimize for content people want to pass along. 13. **Content Must Fit The Funnel:** Know if you’re aiming for attention (top of funnel), education (middle), or conversion (bottom)—and plan your content mix accordingly. 14. **Infuse Brand and Product Authentically:** Entertain first, but always find clever ways to showcase your product or message. ### Mindset & Growth 15. **Think Audience-First, Not Brand-First:** Design content for what your ideal user finds entertaining, useful, or shareable—not what you want to “broadcast.” 16. **Build in Public:** People love transparency and authentic stories. Share the real journey, good and bad. 17. **Prioritize High-Quality Human Creativity over Automation:** Use tools and AI to help, but the best concepts and relatability come from real humans. 18. **Keep Learning & Stay Humble:** Stay curious and always test new ideas, formats, and platforms. There’s no one “right” way. 19. **Engagement is Earned, Not Hacked:** Focus on producing compelling content instead of relying on shortcuts like engagement pods. 20. **Celebrate Your Progress & Have Fun:** Results build slowly at first, but the learning, networking, and opportunities along the way are invaluable. These maxims not only reflect ClickUp’s journey from scrappy start to content powerhouse, but serve as a pragmatic and inspiring guide for anyone wanting to grow through content in today’s digital landscape.

Interview Breakdown

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In this episode of Uploading..., ClickUp’s founding member and Head of Social Marketing, Chris Cunningham, shares the inside story of transforming ClickUp’s content strategy from humble beginnings into a $4B content powerhouse. Discover the tactical approaches and content systems powering hundreds of millions of monthly impressions—and how you can apply these learnings to supercharge your own brand. Today, we’ll cover: - How ClickUp’s content journey started small and evolved into a viral marketing machine - Key pivots, bets, and breakthroughs that defined their content strategy and scaled their reach - Building scalable, repeatable systems—and the secrets to running a “writer’s room” for business content - Balancing top-of-funnel entertainment with product-driven content to drive real business results - Tactical advice for creators and teams looking to scale content, measure impact, and build unstoppable brand engines

Short Recap

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On this episode, Chris Cunningham reveals the playbook behind ClickUp’s $4B content engine, sharing how he scaled their social presence to over a billion impressions a year with a data-driven, creator-led strategy. It’s a deep dive into building viral, repeatable content systems and a team culture that turns brand engagement into real business growth—packed with actionable advice for creators at any stage.

1 Hack 3 tips

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Here’s 1 system ClickUp used to build a $4B content engine (you can steal this for your brand): The “Writer’s Room” Content Machine Most brands treat content like an afterthought. ClickUp built theirs like a *TV show*. Here’s the playbook Chris Cunningham (Head of Social Marketing & founding member) shared on Uploading: • Team brainstorms content every Monday (Writer’s Room style) • 9+ ideas get pitched and punched up • Thursdays = *shoot day* (batch filming 7–9 pieces) • 2 full-time creators act as the “faces” of the brand • They test EVERY idea (raps, skits, viral trends, product demos—nothing’s off limits) Here’s why it WORKS: - “Shots on goal” mentality: Most content flops. ClickUp expects it, and out-experiments everyone else. - FORMULA gets refined: After 40 posts, review the hits. DOUBLE DOWN on what works, iterate, repeat. - Entertain *first*, sell *second*: 70%+ of content is funny, relatable, and designed to get shared—even if it isn’t “product-y.” - Product comes *later*: Once you have attention, layer in bottom-of-funnel demos, value props, and retargeting. The result? • 200M+ monthly impressions • Content that closes deals with VaynerMedia and gets execs from massive brands into their DMs • Fans who *actually* want to see “the HR guys” (their actors) more than another boring SaaS post Want to apply the “Writer’s Room” model? Step 1: **Block time for content—treat it as a priority, not a “nice-to-have”.** (Chris literally schedules his own shoot/edit sessions weekly.) Step 2: **Test every format.** Funny skits. Memes. Trends. Explainers. Product walk-throughs. If it flops? Good. Now you know. Step 3: **Get faces for your brand.** Full-time creators > random employees. (But in the early days, just start with whoever can act on camera.) Step 4: **Review, refine, repeat.** Find your “HR Guys.” Find the format you can own. Make it a show. Step 5: **Start EVERY piece with your ICP’s pain or humor.** Generic = invisible. Relatable = viral. It’s about building a content ENGINE—not just posting once and praying. For B2B, brand, or *anyone* scrapping for attention: Stop winging content. Build your own writer’s room. Steal the ClickUp playbook. (Content compounds. And consistency = exponential results.)

Short Blurb

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E71: The Playbook Behind ClickUp’s $4B Content Engine In this episode, I sit down with Chris Cunningham, founding team member and Head of Social Marketing at ClickUp—the productivity powerhouse now valued at over $4 billion. Chris pulls back the curtain on how ClickUp built a content machine that regularly brings in 200M+ monthly impressions and has generated over a billion impressions in 2024 alone. On today’s episode, you’ll learn: - How to start scrappy and scale a B2B content engine (even with a tiny team) - The high-impact pivots and bets that shaped ClickUp’s viral content strategy - How to combine entertainment and product storytelling for brand AND business growth - Proven systems for building repeatable, engaging content (and keeping your team on track) - Why measuring, iterating, and tying content back to revenue is key (with real examples) Fun fact: Did you know ClickUp’s first major content breakthrough came from hiring a single TikTok creator on contract—and that move ended up helping close massive enterprise deals (including VaynerMedia)? If you’re a founder, marketing leader, or creator looking to turbocharge your content strategy and translate attention into business growth, this episode is packed with practical takeaways from one of SaaS’s fastest-growing brands. Tune in now to get the inside playbook—and don’t forget to check out the show notes for Blaine’s new private community for content creators. Listen now!

New Idea

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Idea #1: Building a Repeatable Viral Content Engine Transform your brand’s reach by building a scalable, repeatable engine for viral content. Here’s how ClickUp put this into practice: 1. Developing “Shows” with Dedicated Creators: Chris Cunningham described hiring in-house content creators (like “Luke” and “Adam,” the HR guys) whose main job is to consistently generate content. Rather than relying solely on ad hoc employee contributions, ClickUp established a creator-driven writers’ room that operates like a mini media company, churning out regular scripts, testing concepts, and iterating weekly. This factory approach turns brand content into a series of recognizable, repeatable formats that audiences look forward to. 2. Data-Driven Testing and Iteration: ClickUp emphasizes “shots on goal” and low-budget testing—creating 40 videos, reviewing the results, and then doubling down on the formats that work (like the recurring “HR Goes Hard” skits). By measuring likes, views, and especially shares, the team refines content formulas and ensures that winning ideas are reused and evolved for even greater reach. 3. Top-of-Funnel Content with Funnel Retargeting: Instead of focusing content solely on product features, the team prioritizes comedy, relatable business moments, and trending memes to attract massive top-of-funnel engagement. But this isn’t just for laughs: ClickUp directly attributes high-value deals (such as VaynerMedia) to this content-first approach, using retargeting strategies to pull viewers down the funnel with recognizable characters and personalized follow-ups. By combining creator-led production, relentless iteration, and a full-funnel awareness strategy, ClickUp built a content machine capable of generating hundreds of millions of impressions a month—proving that a repeatable system is the backbone of any viral content engine.

1 Key Learning

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Build an Agile, Iterative Content Engine Creators and teams should prioritize rapid experimentation—taking lots of calculated, low-budget "shots on goal"—and rigorously double down on what works based on real audience feedback. Instead of pouring resources into big bets right away, ClickUp’s approach shows that consistently testing diverse, lightweight content formats enables you to identify repeatable winners. As engagement grows, invest more in proven strategies, hire standout creators, and refine your system without overcomplicating production. This content-first, iterative mentality empowers teams to stay nimble, learn fast, repurpose efficiently, and unlock outsized organic growth—all while keeping costs low until ROI is clear.

Hustle Thread

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Tweet 1: Chris Cunningham started as a scrappy founder in North Carolina. He lost everything building a Snapchat competitor. But he didn’t quit. Today, he’s Head of Social Marketing at ClickUp—driving billions of impressions. Here’s how he built a $4B content engine: 🚀 Tweet 2: Meet Chris Cunningham (@ChrisClickUp), founding team at ClickUp. From broke entrepreneur to architect of SaaS’ wildest content machine. This is how ClickUp’s viral engine was built—one low-budget bet at a time. Tweet 3: After his early startup flopped, Chris and friends moved to Palo Alto. They pivoted: built ClickUp from scratch, living in a shared house. Total grind—he was also the first sales AND customer service rep. Tweet 4: Early days were tough. No big budget. Chris tried everything: videos, raps, hustle, shot after shot. He believed in content, not just cold calls. His breakthrough? Betting small—hiring a single creator. Tweet 5: He recruited “Luke in the blue shirt”—their first comedy creator. 6 weeks in: their first viral hit (3M+ views). The board doubled down. Soon, a team of creators churned out daily scripts and skits. Tweet 6: Clicks and virality were only half the story. It wasn’t just for laughs—ClickUp closed huge deals from social. Chris tracked everything—from reposts to personalized videos for prospects. Tweet 7: By 2024, Chris’s team built a repeatable system: Writer’s rooms, weekly shoots, omnichannel repurposing, and relentless testing. Consistent content. Constant iteration. Laser-focused on their ICP. Tweet 8: From broke founder to B2B content powerhouse, Chris Cunningham turned small bets into billions of impressions— And proved viral content can drive real business. Tweet 9: If you’re just starting out? Build in public. Make tiny bets. Focus on consistency over perfection. Chris did it. You can too.

🧿 Viral Breakdown & CTA

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Why does your B2B content flop, even with great ideas? Want to build a content engine that fuels brand AND leads? Here’s how ClickUp grew from scrappy posts to a $4B content powerhouse—without burning cash. I’m sharing insights straight from Chris Cunningham, ClickUp’s Founding Team member and Head of Social—his content playbook generated 1+ billion impressions in 2024 alone. He scaled from cold calls to 200M monthly views (and counting). This is how real B2B content gets done. So what separates a viral B2B engine from endless “meh” posts? Let’s break down ClickUp’s 3 content engine power moves: 1. **Take “Shots on Goal”—But Make Them Smart** You need volume to find your winners, but don’t just spray and hope. Chris’s early days? He tested raps, skits—anything to stand out, all done on the cheap. Once he found repeatable hits (think: comedy skits with real creators, not random staff), he doubled down. Don’t wait for the perfect idea—launch, track, and scale what works. Iterate relentlessly, but with intent and a clear hypothesis on what your audience cares about. 2. **Hire Real Creators, Not Just Employees** Most B2B brands shove content work onto whoever’s around. ClickUp treats content like a show: they hired dedicated actors, built a writer’s room, and set strict “production days.” If you want virality and brand love, get people who live and breathe content—don’t just pass the mic at random. Start with a single creator if that’s your budget—just prove results and ramp up from there. 3. **Mix Funnels: Entertain First, Sell Second** Almost 70% of ClickUp’s output? Relatable, funny, or industry-aware skits for top-of-funnel awareness. Entertain, educate, or empathize **before** you ever demo the product. The “HR guys” aren’t pitching features—they’re winning followers who later convert. Then, retarget those warmed-up audiences with contextual product bits and unbeatable ads. This balance keeps your pipeline AND your brand growing. Want these secrets straight from unicorn founders and operators? Follow DTC Pod for more tactical playbooks like this—tune in to learn from the minds shaping today’s top Creator and Commerce content engines. Your growth starts here.

Uploading... Titles

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Chris Cunningham, Head of Social Marketing ClickUp – The Playbook Behind ClickUp’s $4B Viral Content Engine Chris Cunningham, Head of Social Marketing ClickUp – How To Build A B2B Content Machine: 1 Billion Impressions, 200M Per Month Chris Cunningham, Head of Social Marketing ClickUp – How ClickUp Turned Relatable Skits Into Inbound Leads & $4B Valuation Chris Cunningham, Head of Social Marketing ClickUp – Inside ClickUp’s Content Factory: Going From Zero To 1 Billion Impressions Chris Cunningham, Head of Social Marketing ClickUp – Scaling B2B SaaS Through Comedy, Creators, & 300 Million Monthly Impressions

Twitter Post 1

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This behind-the-scenes play turned ClickUp into a viral machine. Hiring one in-house creator (not just regular employees!) led to 25M monthly views in under 2 months. Bringing on dedicated content talent can be a game-changer for B2B brands.

Mindsets

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If you’re looking to build a serious content engine (like ClickUp’s), here are 3 mindset shifts to help you get started: 💭 Shift from “big splash” thinking to *shots on goal*. Instead of betting everything on one expensive campaign, treat each content effort as a calculated, low-budget experiment. The more tests you run (and learn from), the faster you’ll discover what works for you and your audience. 💭 Treat content as a business priority, not an afterthought. Rather than waiting for a free moment to create, block time on your calendar specifically for content—just like any other critical task. As Chris shared, consistency compounds; the rewards for showing up regularly are bigger than you think. 💭 Focus on building *systems and formulas* instead of chasing trends. Virality isn’t luck—it’s iteration and analysis. Use data (like which videos get the most shares), refine winning ideas, and create repeatable content series. When you treat your content like a product—with feedback loops and ongoing improvements—you’ll see compounding results. Want more actionable shifts and behind-the-scenes strategy? Dive into this week’s episode of Uploading for a playbook you can follow, whether you’re a solo creator or scaling a team.

Future State, 6 reasons post

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In 12 months, ClickUp’s content engine generated over 1 billion impressions, broke into pop culture, and directly contributed to 8-figure deals—all with a lean team and a process anyone can replicate. But most B2B SaaS brands are still stuck in old-school content ruts: low reach, low engagement, negligible impact on growth. Here’s how you can transform your brand from invisible to irresistible—and 6 moves to get there: BACKGROUND: The content game has changed. For most teams, the “old school” playbook looks like this: **Old Content Engine:** - Every post reads like a pitch deck. - Slow, siloed output limited to blog posts. - “Social” = irregular, safe, or stale company updates. - Marketing and sales fight over lead-gen scraps. - Top creators work with B2C brands…only. **Even Better Future State:** - Viral video + memes meet B2B: high volume, high-shareability content. - Dedicated in-house creators who are part of the culture—not just borrowed talent. - Collaborative, writer’s room creativity with 7+ new assets/week. - Company execs (CEO, Heads of) join the content engine—everyone becomes the brand. - Content drives full-funnel: brand awareness, engagement, and direct inbound revenue. - Quick feedback, fast testing, and compounding content IP. At ClickUp, repeatable, high-performing content isn’t some magic accident or just flashy top-of-funnel play. It’s responsible for landing whales (think VaynerMedia), compressing sales cycles, and creating an audience bigger than most media brands. Here’s how ANY B2B SaaS or creator-led org can make the leap—and what I’d do if I was starting from scratch: **Here are my 6 recommendations:** 1. **Prioritize Recruiting In-House Creators** Hire content creators as a core part of your marketing team—not an afterthought, not just agencies. Make them owners, not vendors. 2. **Run Weekly Writers Rooms** Act like a media company. Brainstorm, pitch, and punch up ideas every Monday. Build recurring “shows” for your ICP, not random one-offs. 3. **Test Relentlessly—Then Repeat Winners** Publish 40+ videos before calling anything a “winner.” Double down on repeatable formats (like ClickUp’s HR Guys) that hit share-worthiness and fun. 4. **Mix Brand Content with Bottom-of-Funnel Plays** 70% fun/relatable content, 20% product demos, 10% pure thought leadership. Don’t just sell—build relationships *then* retarget like a pro. 5. **Bring Everyone Into the Content Machine** Get execs, founders, and even users making content. Personalized videos to close deals, C-suite LinkedIn posts, and UGC for social proof. 6. **Measure by Impact, Not Just Impressions** Track leads, influenced deals, and even “soft closes” (like prospects referencing viral content). Use custom CTAs, QR codes, and retargeting—all tied back to business goals. The end result: viral growth, engaged communities, and a content flywheel that feeds sales, hiring, product feedback, and beyond. P.S. How is your team building its content engine? What’s the ONE change that would 10x your reach and impact—dedicated creators, a weekly writers room, or something else? Drop your playbook below. Let’s build the next $4B content machine together. 👇

Workbook

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Absolutely! Here’s a comprehensive workbook based on the episode *Uploading...: The Playbook Behind ClickUp’s $4B Content Engine* with Chris Cunningham and host Blaine. This workbook is designed to help individuals or teams apply the lessons from the episode to their own content or brand-building efforts. --- # Workbook: Building a Content Engine – Lessons from ClickUp ## Introduction This workbook takes you through the strategies and tactical steps discussed by Chris Cunningham, founding member and Head of Social Marketing at ClickUp, as he outlines how ClickUp turned its content from humble beginnings into a multi-billion dollar, high-impression engine. Each section contains prompts, exercises, and checklists to help you operationalize these lessons in your own context. --- ## Section 1: Building Your Foundation **Exercise 1: Assessing Your Starting Point** - What is the current state of your content operation? (Describe your platforms, frequency, team structure, and any existing traction.) - What’s your biggest challenge with content creation right now? - What does success look like for you over the next 6-12 months? --- ## Section 2: The Shot-on-Goal & Bet-Making Mindset **Key Takeaway:** Early-stage content is about experimentation, low-budget bets, and volume. **Exercise 2: Brainstorm “Shots on Goal”** - List 10 low-cost content ideas (video, written, audio, image) that you can experiment with over the next 30 days. - Who on your team or in your network can help you produce these fast? - Assign a small budget (if any) and timeline to each. **Checklist:** - [ ] Clear hypotheses for each experiment (Why might this work?) - [ ] Lightweight production (Can you make it quick & cheap?) - [ ] Commitment to volume (Aim for 20-40 pieces before assessing results) --- ## Section 3: When to Invest in Specialists & Content Creators **Key Takeaway:** Hire or contract creators for sustained, high-quality output. **Exercise 3: Evaluate Your Creator Gap** - Are you relying solely on team members for content, or do you have access to professional creators? - Identify at least one creator whose style aligns with your brand and reach out for a collaboration or contract. - Outline your “bet” (e.g., "In the next 8 weeks, can this creator help us break past *X* metric?") --- ## Section 4: Content Mix & Strategy **Key Takeaway:** Balance viral/entertaining content with educational, product, and thought leadership types. **Exercise 4: Content Funnel Mapping** - Who is your ideal customer profile (ICP)? - For each platform (e.g., LinkedIn, Instagram, TikTok, YouTube), list: - Top-of-funnel ideas (entertaining, broad awareness) - Middle-of-funnel ideas (educational, use-case, challenges) - Bottom-of-funnel ideas (product demos, testimonials, case studies) - Assign tentative ratios (e.g., 70% top, 20% mid, 10% bottom for brands at scale; see Chris’s hierarchy.) --- ## Section 5: Repeatable Systems & The Writers’ Room Approach **Key Takeaway:** Use “writers’ room” sessions, repeatable formats, formula-driven testing, and batch production. **Exercise 5: Create Your Weekly System** - Block out time for ideation, scripting, and batch recording (Chris recommends a Monday pitch session, Tuesday selection, Thursday shoot.) - List team members/roles who are accountable for each step. - What “repeatable series” or characters could you develop as recurring content? **Template: Writers’ Room Agenda** - Review previous week’s hits/misses - Pitch 5-10 new concepts - Select 3-5 to produce - Assign scripting roles - Block out shoot/edit slots --- ## Section 6: Measurement, Iteration, and Scaling **Key Takeaway:** Test, iterate, double down on what works, and use data for decisions. **Exercise 6: Metrics & Feedback Loops** - Define 2-3 key metrics to track weekly/monthly (e.g., Impressions, Shares, Signups from content) - Use qualitative feedback (e.g., sales team anecdotes, DMs mentioning your content) as another success signal. - After 8 weeks, review: What repeated themes/formats performed best? --- ## Section 7: Personal & Team Accountability **Key Takeaway:** Prioritize content just like any other core business task—schedule it, systematize it, and don’t skip. **Exercise 7: Commitment Contract** - When and how will you (or your team) block time for content creation? - Who will hold the team accountable for hitting the weekly production and publishing targets? --- ## Section 8: Going Beyond – Testing New Platforms and Trends **Key Takeaway:** Once you hit saturation, start researching new content forms (YouTube, episodic shorts, micro-influencer collectives). **Exercise 8: Next Platform Playbook** - Pick one new platform or content style (e.g., YouTube Shorts, “man on the street”, micro-creator network). - Research best-in-class examples in your industry. - Plan 2-3 small experiments for next month. --- ## Reflection & Action Plan - Summarize the 3 biggest insights from this exercise that you’ll try first. - What’s your “Big Bet” for the next quarter? - Schedule a follow-up to review results and iterate. --- ## Resources / Further Listening - Follow Chris Cunningham: [Instagram: @Cunningham], [LinkedIn: Chris ClickUp], [Twitter/X: Chris ClickUp] - Learn more about ClickUp and their content engine at [ClickUp.com] - Listen to the full episode for voice context or additional nuance. --- **Congratulations! You’re now equipped to start building your own scalable, high-impact content engine—just like ClickUp.** If you’d like this in a downloadable/printable format, let me know and I can format it as a PDF or worksheet.

Tweet thread on learnings

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Tweet 1: So @ClickUp’s $4B content engine is breaking the internet right now: 🔥 1B+ annual impressions 💥 200M+ per month 🌎 Turned social into a demand machine My biggest takeaway from @chrisclickup, Head of Social Marketing, on building a viral B2B content factory: 👇 --- Tweet 2: 1. Consistency > Inspiration Chris blocks time EVERY week—no matter what—to shoot 4–5 videos. Content isn’t left to “when I have time.” It’s a scheduled, recurring task, just like any other. Consistency compounds. Missing weeks is what kills content momentum. --- Tweet 3: 2. Your First Bet Will Probably Miss—Adjust Fast The team made raps, skits, and random content. Nothing hit—until Chris hired a comedic creator, then doubled down when a video finally popped. You need many “shots on goal”—quick, cheap, and ready to pivot when you see signals. --- Tweet 4: 3. Build a “Writer’s Room”—Not a Content Silo Every week there’s a legit writers’ room. 9+ ideas get pitched, only the best are filmed. Regular table reads, feedback, iteration. Content isn’t magic—it’s process, creative rigor, and iteration. --- Tweet 5: 4. Make Top of Funnel FUN—Then Find the Business The viral HR Guys aren’t selling ClickUp on the nose. They entertain first. But those characters reappear in retargeting ads, demo videos, and closing deals. Bottom line: Fun is the entry point. The funnel comes later (and sales loves it). --- Tweet 6: 5. Test, Track, Repeat Like a Machine Nothing is random. They AB-test hooks, content lengths, and platforms. Vids that pop get rerun with new twists. Custom content wins deals (even a personalized video for McDonald’s execs 👀). Everything that works gets systematized and repeated. --- Tweet 7: 6. Start Yourself, Then Bring in Creators It started with scrappy, solo videos. But Chris’s bet: every brand will eventually have in-house creators and actors. Don’t wait until you’re “big.” One creator, then two—test, prove value, then scale. --- Tweet 8: The Ultimate Playbook: - Block recurring time—no excuses - Take *cheap*, fast swings - Treat content as a team sport - Entertain first, sell later - Track everything, automate what works - Creators are not optional—they’re your edge This is how ClickUp turned content into a $4B growth engine.

Youtube Description

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How ClickUp BUILT a $4B Content Engine (and How You Can Do It Too) Unlock the Playbook Behind ClickUp’s Viral Content Machine! 🚀 Get an inside look at the strategies, systems, and creative pivots that drove ClickUp’s content engine to generate over 1 BILLION impressions in 2024—and helped them become one of the world’s top SaaS brands, valued at over $4B. 💡 Want to scale your brand and crush your content goals? Learn from ClickUp’s Head of Social Marketing and founding team member Chris Cunningham as he breaks down the exact methods he used to turn ClickUp’s humble social beginnings into a world-class, omnipresent content powerhouse. Apply to the (FREE) Uploading community to scale your personal brand and learn from top creators: https://castmagic.io/uploading Here’s what I’ll cover in this video: How to Start a Content Engine from ZERO: Chris shares the behind-the-scenes of ClickUp’s earliest content moves, how they experimented with low-budget “shots on goal,” and why scrappy iteration beats overthinking every time. From Sales to Social: Discover why inbound, content-first growth now outpaces outbound in B2B SaaS—and how to build a system that turns impressions into real business results. The Power of In-House Creators: Learn why hiring full-time actors and writers can supercharge your brand’s voice (plus tips for finding and integrating creators into your business). Content Systems & Culture: Get the blueprint for building a “writer’s room,” running consistent brainstorming, and producing daily viral-worthy videos—even if you’re a small team or just starting out. Content for Every Funnel Stage: Explore ClickUp’s mix of top-of-funnel viral skits, mid-funnel product education, and bottom-of-funnel conversion strategies (including genius ways to personalize content for high-value sales deals). How to Measure & Monetize Your Content: Practical insights into tracking, attributing, and proving the ROI of content—straight from ClickUp’s billion-impression playbook. Going Viral (for Real): Chris reveals what makes content explode in 2024, the keys to highly shareable ideas, and why relatability > algorithms. Content Creation Workflow: Hear how Chris and the ClickUp team batch content, leverage AI tools for scripting and repurposing, and keep their production moving—without burning out. Scaling Up (and Starting from Scratch): Whether you’re at $0 or $4B, you’ll hear step-by-step advice for building your own repeatable, monetizable content engine, including how to build in public and attract talented creators. PLUS: Secrets to platform strategy (LinkedIn vs TikTok vs Instagram), handling scheduling and posting, and the experiments ClickUp is running next to grow from 200M to 300M monthly views! This is a must-watch for anyone serious about content marketing, SaaS, B2B growth, or building a personal or business brand that stands out in 2024. Don’t miss out—hit subscribe and drop your biggest questions about content below! — Podcast: Uploading… Episode: The Playbook Behind ClickUp’s $4B Content Engine Host: Blaine Guest: Chris Cunningham (Head of Social Marketing, ClickUp) 🔗 More resources and community info in the show notes!

Simplify

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Absolutely! Here’s a simplified summary of the main ideas from the transcript: - ClickUp’s Marketing Journey: Chris Cunningham shared how ClickUp started small—originally just a few people making content on a tight budget—and evolved into a platform that now gets hundreds of millions of impressions each month. They experimented a lot, learned from what worked and what didn’t, and slowly scaled up. - Content Strategies: At first, Chris made videos himself, tried different styles (even rap), and brought in a professional creator when things needed to level up. The big lesson: Hire talented creators who know how to make engaging content if you want to stand out as a company. - Different Content for Different Goals: ClickUp mixes funny, relatable videos (to get attention and build brand recognition) with educational or product-focused content (to show what ClickUp actually does). They focus heavily on platforms where their target customers are, like LinkedIn, Instagram, and TikTok. - Consistency Is Key: They have regular “writers room” meetings to brainstorm ideas, and batch-shoot their videos once a week. Chris blocks time on his calendar to create content so consistency never slips, even if he’s busy. - Tracking Results: ClickUp measures what content performs best, then repeats winning formats. They always look at what brings real business value—such as tracking leads from viral videos or making personalized videos for potential big clients. - Build in Public: For those just starting, Chris suggests showing behind-the-scenes and being transparent about the journey. Later, as you grow, bring on creators to produce better content at scale. - Virality Formula: To create content that goes viral, focus on being as relatable, human, and shareable as possible. Look for the kind of videos people want to send to their friends or coworkers because it reminds them of someone. - Content Mix: Their current mix is about 70% fun, attention-grabbing content, 20% product-focused, and 10% trend-based or thought leadership—but if you’re a smaller company, you might want to do more product content. - No Shortcuts: They prefer to post content natively, not use scheduling tools or engagement groups, because they find better results this way. - Always Testing: Platforms and trends change, so keep experimenting, look out for new platforms, and adapt your strategies. Let me know if you’d like an even simpler version or if you want this broken down by topic or question!

Uploading LinkedIn-YouTube

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@Chris Cunningham has generated billions of impressions as a founding team member and Head of Social Marketing at @ClickUp, powering their journey to a $4B+ valuation. Chris joins @blaine on this week’s episode of Uploading to dive into the playbook behind ClickUp’s viral content engine — from scrappy early days and hiring dedicated creators, to building brand voice, iterating on content bets, and turning entertainment into measurable pipeline. We break down content systems, omnichannel growth strategies, and actionable advice for brands and creators aiming to scale from zero to millions (and beyond). Full episode here: [YouTube link] #UploadingPodcast #B2BMarketing #ContentStrategy #BrandGrowth #SocialMedia #SaaS #CreatorEconomy

5 Characteristics of Winners

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Based on the insights from our latest episode with Chris Cunningham, here are five characteristics that set winning content teams and creators apart: ✅ Relentless testing—“shots on goal” mentality to iterate and find what works ✅ Calculated risk-taking—starting small, placing bets, and doubling down on traction ✅ Omnipresence—showing up across multiple platforms, tailored for each audience ✅ Process-driven creativity—building repeatable systems (like a writer’s room) for consistent, high-quality output ✅ Customer obsession—deep focus on ICP, not just chasing virality, but driving business impact #ContentEngine #PersonalBranding #ContentWinningMoves

The Rule, The Process, Keys to Success

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ClickUp’s $4B Content Strategy is a perfect example of the “Shots on Goal” rule in action. When it comes to building a content engine, Chris Cunningham and team came at it with a simple, powerful process: prioritize taking a ton of smart, calculated shots—test, iterate, and bet on what works. The general rule: Don’t over-invest, don’t overthink, and definitely don’t expect your first videos to go viral. Instead, focus on putting a lot of content out there (but cheap and scrappy!) and let the numbers be your guide. For ClickUp, that meant everything from Chris making his own low-budget raps and skits in the early days, to hiring one creator, then doubling down as the content started taking off. Every Monday, they run a writer’s room to brainstorm batch ideas. Every Thursday is a full shoot day. Then it’s back to editing, testing, iterating, and pushing it live, week after week. The process is about three things: 1. Relentless experimentation — get 40 videos out there, see what hits, and double down. 2. Mix up your content: 70% relatable or funny, 20% product-focused, and 10% educational or trending. 3. Don’t become obsessed with perfection—block time weekly, batch what you can, and trust the compounding effect. The key to broader success? Build for your audience, not just for virality or vague metrics. Chris and his team constantly talk to customers, test ideas, and use their content to create genuine connections. They know most content is for top of funnel, not direct selling—and that’s by design. Don’t try to be everything to everyone. ClickUp’s playbook says: take your “shots on goal,” have a process, iterate with intention, and build for the people who care. The rest takes care of itself.

3 bullets 3 bullets (dakota)

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Most of the SaaS brands crushing 200M+ monthly impressions: • Aren’t big-budget Super Bowl advertisers • Didn’t start with a full media team • Didn’t have viral creators on payroll They just: • Take endless “shots on goal”—and learn from each one • Hire creators, not just employees • Test, double down, and iterate relentlessly Eyeballs lead to business growth. But it’s not about chasing virality for its own sake—it’s about building a machine that entertains, educates, and converts your ideal customer. Your billion-view brand engine is more repeatable than you think. (If you want to see what that looks like in action, check ClickUp’s feed—or listen to Chris Cunningham break it down on Uploading…)

Framework To Build From Scratch

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If I had to rebuild ClickUp’s $4B+ content engine from ZERO, here’s the playbook I’d use (this is the strategy ClickUp used to hit 1B+ impressions in 2024): To turn strangers into followers (and followers into customers), you need 3 things: • Get in front of your audience (top of funnel) • Keep them coming back (relatable & educational content) • Show them how you solve their problems (product in action) So, how did ClickUp do this—and how can you? By building your OWN content machine with these strategies: 1. Test Relentlessly (Shots on Goal) Take as many “shots” as possible. Low-budget, fast iterations. 40 days of testing different styles—from funny skits to trending topics to simple relatable posts. 2. Bring in Creators, Not Just Marketers The best B2B brands now have dedicated, in-house creators. Hire for talent, not just resumes. Give them room to experiment. 3. Play the Content Mix 70% Entertaining/Relatable: – Workplace humor – Skits about your ICP’s daily life – Trending formats 20% Product-Focused: – Show your tool in action – Customer stories 10% Thought Leadership: – Founder/CEO POVs – Share real lessons Mix & match for every platform—LinkedIn isn’t TikTok, and vice versa. 4. Repurpose & Personalize Turn one shoot into 5+ assets. Send custom videos to high-value leads. Leverage AI for captions & repurposing, but keep core creative HUMAN. 5. Build In Public Own your story—even if it’s messy. People want transparency and behind-the-scenes. 6. Measure & Iterate Chase shares, not just likes. Track bottom-of-funnel: QR codes, custom links, feedback from sales. Virality is great—conversions are better. Bottom line: Consistency beats perfection. Volume leads to breakthroughs. Don’t talk AT your audience—create FOR them. Start stacking these pillars and you’ll build a content engine that drives real business, not just vanity metrics. (P.S. If you want to see real examples, check ClickUp’s Instagram or LinkedIn. It’s all there.)

3 Success Strategies

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1. Lean Into Repeatable Content "Shows" Instead of relying on a handful of one-off viral hits, the ClickUp team treats content creation like building out a TV lineup—with repeatable “shows” starring memorable personalities. Chris Cunningham’s playbook is simple: Identify formulas that resonate (like the “HR Guys” sketch series) and double down. Regularly test dozens of concepts, then refine and repeat top performers on a predictable schedule. Viewers know what to expect, start to anticipate the next episode, and your content operation becomes easier to manage and scale. When your audience can’t wait for the next installment, you know you’re building something sticky. 2. Test Relentlessly, Iterate Without Ego If you want to drive 200+ million monthly impressions, you can’t afford to rest on old ideas—or your laurels. Chris emphasizes the importance of putting constant “shots on goal,” but always with small, calculated bets and low budgets. Early on, ClickUp’s content didn’t have a magic formula. It was a whirlwind of experiments: raps, skits, and homegrown videos. Only by rigorously testing (40 posts before evaluating a new series!) and closely analyzing what hit—and why—were they able to uncover repeatable winners. Don’t get attached to your favorite ideas. If the data doesn’t back it, move on. Consistent iteration is how you transform random hits into a viral machine. 3. Build for the Entire Funnel, Not Just the Feed The most successful B2B content engines look beyond raw likes and top-of-funnel engagement—they architect their output for every stage of the buyer journey. For ClickUp, that means a healthy mix of viral, entertaining skits to drive brand awareness; thought-leadership and value-add content for consideration; and smart call-to-action tactics like product demo videos, QR codes, or custom assets for hot prospects. When a viral character (like the HR guys) is already loved by your target customer, retargeting becomes cheaper and more effective. Think of content as the connective tissue across your funnel—capable of creating leads just as efficiently as a high-performing outbound sales team, but with exponentially greater scale and resonance.

3 Success Strategies v2

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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 Growth 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 Summary

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Chris Cunningham is a founding member and the head of social marketing at ClickUp, the $4B AI-powered productivity platform. Since joining the company in its early days, Chris has been instrumental in developing ClickUp’s brand voice and transforming its social channels into a powerhouse content engine, consistently generating hundreds of millions of impressions monthly. His innovative approach includes building in-house creator teams, leveraging viral video formats, and blending B2B thought leadership with entertainment-driven content. In this episode of Uploading, Chris breaks down the content strategies and systems that turned ClickUp from a scrappy startup into one of the most influential names in B2B SaaS. He shares actionable insights on assembling creator-led teams, testing and iterating content formats, measuring ROI, and integrating content seamlessly across the funnel—from top-of-funnel brand plays to bottom-of-funnel conversion tactics. The discussion also covers advice for brands starting from zero, building a culture of creativity, and scaling content operations for maximum business impact.

Blaine Content Sample

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How ClickUp Grew Their Content Engine to 200M+ Monthly Impressions (and What You Can Steal) A few years back, ClickUp’s social media presence looked like everyone else’s—it was just getting off the ground, scrappy, and nowhere near the billion-impressions mark they’re now hitting in 2024. Fast forward to today: ClickUp is raking in 200M+ impressions every single month, their content is everywhere (literally omnipresent), and they’ve built an engine that not only grows the brand but actually drives real leads and business. Here’s a peek behind the scenes on how Chris Cunningham (founding member + head of social at ClickUp) and team did it, plus the principles you can use to scale your own content game. Background - Started with zero traction & no fancy team—just hustle, trial-and-error, and tons of “shots on goal” - Treated content as a repeatable, test-driven system (not just “one-off” viral moments) - Focused on hiring actual creators, not just asking employees to moonlight as content folks These are the big 4 principles that powered ClickUp’s content engine: 1. Shots on Goal (but Make Them Smart) In the early days, it was all about volume—but with intention and minimal spend. Chris would run tons of low-cost experiments (sometimes even rapping on camera himself) just to see what stuck. Most didn’t blow up, but every experiment was a learning loop. When they found the right formula (i.e., hiring a dedicated creator with a proven track record), they doubled down and scaled it: think “one big bet at a time,” always keeping budgets tight and impact measurable. 2. Omnipresent by Platform & Persona What wins on TikTok isn’t what wins on LinkedIn (or X, or Instagram), so they didn’t force-fit one style everywhere. Instead, the team built “shows” and personas for each channel—comedy for IG, thought leadership for LinkedIn, and tested which segments performed where. Repeatable formulas (like “HR Guys”) were systematized, and if a bit went viral, they’d remix or rerun it with variations, balancing top-of-funnel awareness and middle/bottom-funnel conversion plays. 3. Relentless Iteration & Feedback Loops Every week is a new writer’s room, new ideas, new tests. If it works, do it again (but not too often, or you run it into the ground). If it flops, tweak and retool. Every video, post, or campaign gets rated, analyzed, and either doubled down on or put on ice. And yes, consistency is everything: they block time, batch-create assets, and leverage AI tools to repurpose snippets across channels (without sacrificing originality). 4. Don’t Just Entertain—Integrate With the Funnel Fun skits and viral moments are great, but it’s all connected to pipeline. ClickUp consistently weaves product touchpoints into entertaining formats, tracks leads via QR codes or DMs, and uses custom content to help sales close big deals. When sales teams flag a hot prospect, the content team will even whip up bespoke “HR Guys” videos to push things across the finish line. (Personalization > cold emails, every time.) The Content Split That Works: - 70% top-of-funnel entertainment/brand - 20% product-led or middle-funnel - 10% bottom-funnel/explicit pitch (but this shifts as your company matures) What’s Next? ClickUp’s always hunting for the next “big show”—shifting to YouTube, experimenting with episodic short-form, and testing micro-influencer networks. The process is never finished, but that’s what keeps their engine spinning. Key Takeaways For Your Own Brand: - Treat content as an engine, not one-offs: systematize your process, iterate fast - Hire or work with actual creators—quality shines through - Mix entertainment with education and product, but always tie back to your funnel goals - Be obsessed with feedback and relentless improvement If you’re building a content engine, borrow these tactics—and go bigger on your bets with every signal you get. Would love to hear how you’re scaling your content systems!

1 most actionable piece of advice

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Block out weekly time to consistently create and batch content.

Gregs LinkedIN Example

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the $4B content engine playbook (the ClickUp edition) 1. start lean: you’re the sales rep, marketer, and creator 2. take constant shots on goal—iterate fast, test cheap 3. hire creators, not just employees—turn your office into a studio 4. scale with repeatable “shows” & characters (think HR Guys, inside jokes, skits) 5. mix brand and product: 70% relatable bangers, 20% product, 10% thought leadership 6. build in public—audience loves the journey, not just the result 7. weaponize relatability—content = shares = impressions = leads 8. treat content as another task—batch, block time, keep it non-negotiable 9. viral is a formula: strong hook, deep human insight, perfect shareability 10. amplify with AI for copy, not for concepts—your brain, Claude’s keyboard old b2b playbook: cold calls and outbound sales the new playbook: viral content machines + inbound mountains to win: - ICP obsession—know who you’re creating for, inside jokes included - low budget bets (prove, then invest) - an internal “writer’s room” (Monday ideas, Thursday shoots) - omnipresence—LinkedIn, Instagram, TikTok, then layer on YouTube, X - track & monetize: QR codes, retargeting, personalized videos 2023: “every company needs a sales team” 2025: “every company needs creators on payroll” ClickUp did it: - 1 creator → 25M monthly views → full team → 200M+ impressions/month - content closes deals (ask VaynerMedia, GaryVee saw the posts) - don’t overthink gear—iPhones and office staff can go viral - virality? Shares > likes, always Pro tip: Scaling? Early: 40% product, 40% entertainment, 20% authority Growth: 70% banger, 20% product, 10% trends/education You can build a viral content engine with less than you think. Start with shots on goal. Find your HR Guys. Iterate, punch up, post. Happy uploading.

Questions Shownotes

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How did ClickUp’s content engine evolve from humble beginnings into a viral B2B powerhouse? What was Chris Cunningham’s journey from founding an agency and failed social app to building ClickUp? Why did ClickUp initially decide to take a “shots on goal” approach with their early content? How did hiring their first full-time content creator transform ClickUp’s brand and social media strategy? What was the breakthrough moment that proved the ROI of ClickUp’s content investments to leadership? How does Chris design repeatable, scalable content “shows” to consistently reach hundreds of millions of impressions? Why does Chris believe every modern brand will need to hire dedicated content creators to compete? How does the content strategy differ between platforms like LinkedIn, Instagram, TikTok, and X (Twitter)? What roles do entertainment, education, and direct product promotion play in the overall content mix? Why does ClickUp incorporate skits, humor, and relatable workplace scenarios in their videos—and how do these drive inbound leads? How does ClickUp personalize video content for target clients to help close sales deals? How does Chris and his team ensure that even busy executives (like the CEO) consistently create content? Why is batching and blocking content creation time essential for ongoing consistency and growth? Which content ideas and formats does ClickUp iterate on, and how do they determine what “formula” works? What is the “ABCD formula” for content ideation, and how does it drive their testing process? How does ClickUp adapt content for different stages of the marketing funnel, from top-of-funnel awareness to bottom-of-funnel conversion? What metrics matter most to Chris when measuring content success—and why do shares beat out likes? How should early-stage founders and small teams approach content creation before they have ClickUp-scale resources? How is ClickUp planning to scale from 200 million to 300 million monthly impressions, and what new trends are they experimenting with? What actionable advice does Chris offer to creators and marketers who want to build, measure, and monetize their own content engines?

Episode summary

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Chris Cunningham is a founding member and Head of Social Marketing at ClickUp, the AI-powered productivity platform valued at over $4 billion. In this episode of Uploading, Chris takes us inside ClickUp’s $4B content engine, revealing how they scaled from scrappy beginnings to over a billion impressions in 2024. He shares the playbook for building viral B2B content, key pivots that shaped their strategy, and how he built a team and culture that consistently delivers results. Plus, Chris breaks down ClickUp’s approach to balancing brand and performance content, building repeatable systems, measuring ROI, and actionable advice for creators looking to turn content into business growth.

Lead Magnet Idea

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Lead Magnet: **"Build Your B2B Content Engine: The ClickUp Playbook for Viral Growth"** **Description:** This visually compelling, easy-to-follow PDF guide is your actionable blueprint for transforming your B2B content strategy—taking direct inspiration from Chris Cunningham and the ClickUp team’s secrets that drove them from zero to over a billion annual impressions. If you’re a founder or marketing leader looking to scale your content, build a repeatable system, and actually tie your efforts to business results, this toolkit is for you. --- **Components:** **1. The B2B Content Engine Roadmap** - Quick primer on how ClickUp’s approach blends content creation with lead generation and revenue. - “Shots on goal” visual worksheet: Map your own low-cost, high-frequency content experiments based on what’s working for ClickUp. **2. Your First Content Creator Play** - Step-by-step instructions for hiring your first (affordable) content creator or getting started solo—regardless of budget. - Sample contractor outreach email (inspired directly by Chris’ approach with Luke, the “guy in the blue shirt”). - Cheatsheet: “How to Test and Triple Down on Winning Formats” (based on the ABCD formula shown in Chris’s writer’s room process). **3. Repeatable Content Systems for Busy Teams** - One-page “Content Production Sprint” template (Monday: brainstorm, Wed: scripts, Thurs: film, Fri: edit & schedule). - Tips for blocking out time, batching shoots, and using AI tools to repurpose your content for each platform. - Checklist: How to involve your team without disrupting their workflow. **4. The Viral Video Blueprint** - Fill-in-the-blank scripts for highly shareable, relatable posts (steal ClickUp’s “HR Guys,” trend-jacking, and business skit ideas). - Engagement triggers: Make your video content more shareable by focusing on relatability, nostalgia, and inside jokes for your ICP. **5. Content Funnel Calculator** - Visually map your Top, Middle, and Bottom of funnel content with real ClickUp-inspired examples. - Ideal content mix worksheet: Adjust percent of entertainment vs. product vs. thought leadership content for your stage. **6. From Attention to Revenue: Tracking What Works** - Simple dashboard for tracking impressions, leads, and closed deals driven by content. - QR code and retargeting playbook so you can prove ROI from your creative experiments. - Sample personalized “deal closing video” template. **Bonus:** - Visual gallery: 10 winning ClickUp posts (with commentary on what made each work and how to riff on them for your brand). - List of go-to low-cost creator platforms and free tools to launch your content engine now. **Visual Appeal:** - Infographics illustrating “The ClickUp Impressions Engine” - Example content calendars, checklists, and fillable worksheets - Pull quotes and real screenshots from the episode to bring tactics to life --- **Call to Action:** **Download Instructions:** Click the link below to get your free copy of “Build Your B2B Content Engine: The ClickUp Playbook for Viral Growth.” **Invitation to Engage:** Level up even faster! Join our free Uploading Community for behind-the-scenes workshops with creators like Chris, peer feedback, and live Q&A. [Link in the show notes] **Follow-Up Offer:** Want tailored advice? Book a free 20-minute strategy consult with our content experts, or grab a spot in our next “Content Engine Accelerator” cohort. --- **Example CTA:** Ready to turn your content into a brand-building, lead-generating machine? **Download the “ClickUp Playbook for Viral Growth” now!** Get the actionable templates, step-by-step systems, and inside tactics straight from one of SaaS’s most effective content teams. → **[Download Now]** And don’t miss your invite to our free community for exclusive workshops, resources, and expert support—see you inside! --- By drawing directly on the episode’s insights and providing tangible tools, this lead magnet equips your audience to act now—while tying them back to your brand, content, and services for deeper engagement.

5 reasons why with a PS

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I grew ClickUp’s brand to hit over 1 BILLION impressions in 2024 (and we’re going for 300M *per month* this year). Here’s 5 hard-learned lessons behind building a content machine *that actually drives business*—even if you’re starting with zero budget and zero team: 1. Run *calculated* shots on goal. - Treat content like experiments. Start CHEAP, iterate fast. - Instead of “let’s make a viral ad,” try everything—raps, skits, carousels, you name it. - Betting on content means low budgets, small bets, and learning what hits (before you scale it up). 2. Don’t rely on “someone from the office” for content. - Hire or be THE creator, even if it’s just you in the beginning. - A killer content creator will outperform whatever random employee video your team cooks up. - We brought in Luke (aka “the guy in the blue shirt”) on a *contract*—and once the numbers hit, ramped HARD. 3. Build systems, not just one-offs. - Our process? Weekly writers’ room, ideation, punch-up, shoot day, then editors *process* the magic. - Make content a *recurring meeting* on the calendar. Consistency > one-hit wonders. - Use tools (and your product!): block out time, automate tasks, and batch-record to build a true engine. 4. Content isn’t one-size-fits-all. - On LinkedIn: Thought leadership, personal stories, and visuals. - On TikTok/Instagram: Funny, shareable, highly relatable bits (“HR guys”, music videos, quick skits). - Mix education, brand, and product. Only pushing product = zero reach. 70% entertainment/relatable, 20% product, 10% trends/leadership is our current mix at scale. 5. Track, personalize, and close deals with your content. - Get creative with attribution (QR codes, custom videos for sales prospects, even hyper-personalized shoutouts for top target accounts). - Sales team use your *content* as the closer—don’t underestimate inbound and retargeting value. - Content is NOT just “for fun”—it moves pipeline and closes real revenue. You don’t need a $10M ad budget. You just need tight feedback loops, a willingness to experiment, and a relentless, systematic approach to getting 1% better every week. Skip the vanity—commit to the reps. Don’t gatekeep your journey. Build in public. Show the highs *and* the lows. P.S. Want to level up your own content approach? Our new Uploading community just launched. It’s free, vetted, and focused on building your personal brand (for real, not fluff). Apply here: https://castmagic.io/uploading-community Let’s build brands (and business) together.

Episode Notes

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SUMMARY OF EPISODE In this workshop episode of "Uploading...", Blaine is joined by Chris Cunningham, founding member and Head of Social Marketing at ClickUp—the $4B AI-powered productivity platform. Chris dives deep into how ClickUp evolved from scrappy beginnings into a content powerhouse, regularly generating over 200 million impressions a month and reshaping the game for B2B SaaS brands. Blaine and Chris explore: - ClickUp’s journey from early failures to breakout success. - The calculated bets and strategic pivots that fueled viral growth. - Building repeatable content systems—and a team culture that keeps the engine running. - Creative approaches to measuring and monetizing content, from personalized videos to QR-coded campaigns. - Tactical advice for creators and marketing teams eager to scale their content and drive real business results. Chris opens up about ClickUp’s “shots on goal” mentality, what it takes to build a viral content engine on a lean budget, and how to foster a team of full-time creators who operate more like a modern writer’s room than a traditional marketing team. BULLET POINTS OF KEY TOPICS Early Days and Pivots from Failure to Product-Market Fit Chris recounts the journey from running an agency to launching an unsuccessful Snapchat competitor, then pivoting to build what became ClickUp. He discusses lessons learned from setbacks and how those experiences shaped ClickUp’s product and marketing DNA. Strategic Content “Bets” & Hiring Creators [00:05:09] Chris details the “shots on goal” philosophy—prioritizing constant experimentation with low-budget content bets. He shares why he hired a full-time creator, “the guy in the blue shirt,” after recognizing that companies would need in-house creators to stay competitive, and how this move led to breakthrough viral hits and millions of new impressions. Building Repeatable Content Systems & Process [00:07:04] Chris reveals ClickUp’s operational backbone: weekly writer’s rooms, batching video shoots, and assembling a team that iterates obsessively. He explains the ABCD formula for content testing, how to analyze winning posts, and the value of sticking to a cadence—even if it means blocking off calendar time and using AI tools to streamline ideation and editing. Content Strategy Mix: Funny, Relatable, and Product-Centric [00:08:07] Blaine and Chris break down balancing entertainment with intent: using top-of-funnel content for brand awareness alongside product-focused posts for conversions. Chris illustrates how content hooks major clients and supports sales (sometimes with personalized videos for big prospects). Content Platform Tactics: Instagram, LinkedIn, TikTok & More [00:14:31] Chris gives a tour of ClickUp’s video-heavy Instagram strategy, using trends, nostalgia, and “HR guys” skits to maximize engagement. He contrasts this with LinkedIn, where visual carousels and thought leadership take center stage, and shares ongoing experiments with platforms like YouTube and X. Data, Metrics, and Attribution [00:09:53] From QR codes to feedback loops with sales reps, Chris discusses how ClickUp ties content output to real business impact. He shares examples of deals closed after connections made through viral content and the importance of tracking beyond vanity metrics—focusing especially on shares as the metric that drives virality. Advice for Early-Stage and Scaling Brands [00:23:26] Chris outlines what he’d do starting from scratch: “build in public,” document the journey, leverage early team members for authenticity, then reinvest in creators as the brand scales. He emphasizes iteration, learning from the audience, and the importance of understanding your ICP. Frameworks for Virality & Content Ideation [00:25:55] Diving into what fuels ClickUp’s breakout hits, Chris talks about generating “human” content that’s deeply relatable, leveraging nostalgia, office humor, and attention-grabbing concepts. He shares the mindset behind crafting content designed to be shared—and why shares (not just likes) are a top KPI. Content Mix & Funnel Balance [00:37:24] Chris suggests a 70/20/10 content split at ClickUp’s current scale—70% entertainment/relatable, 20% product show-and-tell, 10% trends/thought leadership. For earlier-stage brands, he advocates a heavier tilt toward product until the brand matures. Scaling Creators & Exploring New Content Models [00:41:30 / 00:45:30] Chris discusses hiring full-time actors/creators, pulling in office staff for authentic moments, and future plans to test micro-influencer networks, episodic short-form content, and new platforms like YouTube Shorts and RealShort to sustain growth as ambition rises. Scheduling, Engagement, and Platform Nuances [00:30:55] Manual posting is Chris’s preferred method over scheduling tools, for better algorithmic results and personal touch—plus his take on engagement groups and the ethical balance in platform strategies. __ This episode is packed with actionable insights for founders, marketers, and anyone hungry to build a high-impact content engine with real business outcomes. Follow Chris Cunningham (@Cunningham on Instagram, Chris ClickUp on LinkedIn/X) and ClickUp to see these strategies in action.

Timestamps Trial

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00:00 Uploading Community Announcement & Episode Intro 00:46 Meet Chris Cunningham: ClickUp’s Content Architect 02:11 Chris’s Background: From Agency to ClickUp’s Founding Team 04:05 Early Content Hustle: Sales to Scrappy Content Creation 05:09 Shots on Goal: Low-Budget Bets & the First Creator Hire 07:04 Building a Repeatable Content Engine: Scaling with Creators 08:07 Platform-Specific Content Strategy & Goals 09:53 Linking Content to Business Impact & Funnel Strategy 11:28 Making Content a Team Priority: Systems & Scheduling 13:44 Consistency, Time-Blocking, and Using AI Tools 14:37 Screen Share: Inside ClickUp’s Instagram Strategy 15:38 The ABCD Formula: Testing for Virality 16:09 Case Study: Viral Skits, Trends, & Relatable Office Content 17:49 Leveraging Memes, Trends, and Episodic Content 18:59 Mixing Product & Entertainment in Content Mix 19:29 Operations: Writers’ Room, Shooting Schedule, & Execution 21:09 Getting Employees Involved & Lightweight Content Production 22:34 Adapting Content per Platform & Cross-Posting Wins 23:23 Starting from Scratch: Building in Public & Early Tactics 24:42 Hiring Creators on a Budget & the Iterative Process 25:47 Frameworks for Virality: The Anatomy of a Viral Video 27:41 Winning Concepts: Relatability, Shareability, & Emotional Triggers 29:39 Know Your Audience: Interviewing the ICP for Better Content 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 34:26 Engagement Pods: To Participate or Not? 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 45:30 Micro-Influencer Strategy: Pumping Volume & Testing 46:19 Wrapping Up: Follow Chris & ClickUp; Final Thoughts

About the Episode

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Chris Cunningham is the founding member and Head of Social Marketing at ClickUp, the $4B AI-powered productivity platform that’s become a behemoth in the B2B SaaS content space. Since 2017, Chris has been the driving force behind ClickUp’s viral content engine, leading a team that regularly generates over 200 million impressions a month and has surpassed a billion impressions in 2024 alone. In this episode of “Uploading…,” Chris breaks down exactly how ClickUp scaled from scrappy, experimental content in a crowded market to operating a multi-channel, repeatable content machine. He shares key pivots in their strategy—including the decision to recruit full-time creators and build a writer’s room culture—plus actionable frameworks for developing viral, shareable content across platforms like LinkedIn, Instagram, and TikTok. Chris also dives into creating content that drives real business outcomes, from attracting high-profile clients to integrating content across the full marketing funnel. Whether you’re a founder, marketing leader, or solo creator, you’ll get practical insights on team building, workflow, and using AI to maximize output—along with advice for anyone looking to scale their content and brand in today’s competitive landscape.

Show Notes

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Episode Summary Chris Cunningham, Head of Social Marketing and founding member at ClickUp, joins Uploading to reveal the secrets behind building ClickUp’s content engine—now responsible for over a billion annual impressions and helping grow the company’s value to over $4B. 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. Episode Notes 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 dive into content pivots, hiring creators, their “shots on goal” philosophy, 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. Why B2B content should prioritize entertainment and relatability (and how it still brings in leads) 2. The “writer’s room” approach and cadence for producing high-volume, high-quality content 3. How to build a viral content formula using iteration and trends—plus operational tips for consistency 4. The right content mix for your stage (startup, scaleup, enterprise) and goals (brand, lead gen) 5. Tracking and monetizing content: how ClickUp credits deals to content, retargets prospects, and personalizes sales 6. Actionable steps for solo founders: building in public, hiring creators, and testing quickly on a budget 7. Tactical advice on content batching, AI usage, and workflow for busy execs and marketing leads 8. How “shots on goal,” betting small, and relentless testing underpin ClickUp’s success Timestamps 00:00 — Intro, show updates, and today’s guest: Chris Cunningham of ClickUp 02:11 — Chris’s backstory: ClickUp’s origins, agency days, and building from nothing 05:09 — Early content strategies: shots on goal, low-budget bets, and hiring creators 07:21 — Defining brand messaging: entertainment + product, content briefs, and goals by platform 10:46 — Integrating content into the whole funnel and growth strategy 11:55 — Chris’s weekly content creation routine and tips for busy teams 14:31 — Live walkthrough: ClickUp’s Instagram & content breakdown with real examples 19:28 — Execution: writing, shooting, editing, and bringing in actors or internal staff 23:26 — How to start content from scratch as a solo founder or small team 25:13 — The formula for virality and how to brainstorm shareable ideas 28:29 — Understanding audience and ICP to drive content resonance 30:55 — Manual posting vs. scheduling tools: what works for ClickUp 32:18 — Platform strategies: LinkedIn, TikTok, Instagram vs. YouTube and what’s next 40:27 — Ratio of entertainment vs. product-driven content and how it changes as you scale 41:30 — Building a content team: actors, internal staff, and creators at scale 42:16 — Video length, testing, and best practices for engagement 44:04 — What’s next for ClickUp’s content: new formats, platforms, and tests 45:02 — Micro-influencers, scaling via creator “pods,” and new experiments 46:34 — Where to follow Chris and wrap-up Quotes “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 I brought in an expert—a creator. 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 at a new company—we’re building in public. No actors, just talking about what we’re working on. People love to see it. 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 Follow Chris and ClickUp Instagram: @Cunningham LinkedIn: Chris ClickUp Twitter/X: @ChrisClickUp Email: chris@clickup.com –– For access to the exclusive Uploading community, apply at castmagic.io (link in show notes).

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