Beyond Social
Beyond Social
Vista Social
How ClickUp Went From Unknown Startup to $300M ARR
21 minutes Posted Feb 25, 2026 at 7:00 pm.
Entering A Crowded Market
Founding Story And Early Hustle
Pivot From Social App To ClickUp
Scrappy GTM And AppGator
Winning Customers During Competitor Shutdown
Hiring For Grit Over Big Names
Office, Remote, And In-Person Magic
Mistakes: Hiring, Discounts, And Roadmaps
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Show notes
ClickUp scaled to $300M ARR in one of the most competitive SaaS categories in the world. In this episode, Reggie and Vitaly sit down with Chris Cunningham, Head of Social at ClickUp, to break down the SaaS growth strategy behind ClickUp’s rise — from living in a startup house to becoming a category leader in the project management space. They unpack what it really takes to scale a B2B SaaS company in a saturated market: scrappy go-to-market tactics, early product-market fit lessons, unconve...