E2: Scaling ClickUp into a $4B SaaS Empire with Chris Cunningham Co-Founder of ClickUp

In this energizing episode of the AI for Business podcast, you’ll hear my business partner Brian Hansen in a high-impact conversation with Chris Cunningham, Co-Founder and Head of Marketing at ClickUp. Chris shares the raw, behind-the-scenes story of how ClickUp grew into a $4 billion company by thinking differently, moving fast, and staying scrappy. Recorded live during the AI for Business Virtual Summit, this session is packed with powerful insights for entrepreneurs ready to scale with AI and unconventional marketing strategies.

 

Chris dives deep into the steps that took ClickUp from a tiny startup to one of the fastest-growing SaaS companies on the planet. From building their own lead-generation tools, to going viral on social media, to hiring intentionally and integrating AI across their business, he gives you a transparent look at what it really takes to grow fast without funding early on.

 

Episode Timeline Highlights:

[0:00] Introduction

[1:30] Chris’s backstory and early lessons from a failed startup

[4:20] How scrappiness became ClickUp’s competitive edge

[6:01] Using negative competitor reviews to generate warm leads

[7:03] The strategic customer grab that supercharged their growth

[8:25] Hard lessons on hiring the wrong execs—and how to avoid it

[10:20] Why standing out with bold, human marketing works

[12:44] Social media strategy: how fun content built brand loyalty

[14:01] Humanizing the brand like The Office meets Step Brothers

[15:12] Taking small, smart marketing bets to unlock virality

[18:05] Fundraising advice: when to raise and when to wait

[19:17] How ClickUp replaces dozens of tools in one workspace

[27:32] The AI advantage: ClickUp’s smart features in action

[28:44] Why ignoring AI could put your business at risk

 

5 Key Takeaways:

 

1. Be scrappy and creative – You don’t need big budgets to win early; you need hustle and smart tools.

2. Stand out with your voice – Stop mimicking competitors. Be bold, be human, and be different.

3. Leverage AI across the board – Use AI as a team multiplier for automations, messaging, and workflows.

4. Make calculated bets – Test small, prove results, then scale what works. Don’t wait for permission.

5. Build community and consistency – Content that entertains, educates, or connects will build lasting loyalty.

 

Links & Resources Mentioned:

 

ClickUp – https://www.clickup.com

CoFounders Lab – https://www.cofounderslab.com

Contact Chris Cunningham – [e-mail]

Chris Cunningham on LinkedIn – https://www.linkedin.com/in/chriscunningham

 

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