Episode Summary
In this episode of Chaos to Clarity, Eric Weiss sits down with Gaurav Agarwal, COO of ClickUp, to unpack how one of San Diego’s biggest SaaS success stories built a $300M ARR business by putting product, speed, and customer obsession at the center of its strategy.
Gaurav shares how ClickUp redefined product-led growth, balanced self-serve and sales-assisted revenue models, and built a culture obsessed with iteration and feedback. From eliminating “work about work” to running 100+ experiments per week, this conversation is a masterclass in operational excellence and founder discipline.
This episode dives into:
- How ClickUp grew to $300M ARR from San Diego
- The real meaning of product-led growth (and why it’s misunderstood)
- Finding the line between free and paid features
- How to build a customer-obsessed culture
- Running 100+ experiments per week without chaos
- The secret to scaling operations without killing innovation
- Gaurav’s leadership framework: business first, team second, self third
Why Listen
If you’ve ever tried to scale a SaaS product and found yourself drowning in meetings, tools, and “work about work,” this episode will feel like oxygen.
Gaurav Agarwal, COO of ClickUp, reveals the operational playbook behind one of tech’s fastest-growing companies — the systems, principles, and experiments that took them from startup chaos to $300M ARR.