You might think content from a project management company would be dry, right? Think again.

Today I sat down with Chris Cunningham, a founding member of ClickUp and the head of their social media marketing, to explore their unconventional approach to content creation. Believe it or not, ClickUp isn’t just making business content—they’re breaking all the rules by taking inspiration from comedy and entertainment (think Saturday Night Live) while still delivering value to their audience.

Chris shared how their team takes their content strategy seriously—investing in talent, writing teams, and a creative vision that’s anything but boring. We also talked about how creators can adopt scrappier methods, why it’s important to “take bets off data,” and how reframing embarrassment can unlock your creative potential.

WATCH THIS EPISODE ON YOUTUBE: https://www.youtube.com/heatherparady 

TOPICS FROM THIS EPISODE:

• Scrappy ideas for content creators
• Documenting your journey and leveraging that content
• How to “think in pictures” to spark better ideas
• Ryan Reynolds’ approach to newsjacking (and what you can learn from it)
• How to reframe “embarrassment” as a creator and push through doubt

CONNECT WITH CHRIS CUNNINGHAM:

• Instagram: https://www.instagram.com/cunningham/
• LinkedIn: https://www.linkedin.com/in/chrisclickup/

CONNECT WITH HEATHER:

• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/episodes/64

Mentioned in this episode:

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