How do you know when you’re no longer the right leader for your own company?

After 15 years building Help Scout — shaping its culture, defining its values, and growing it into a successful SaaS business — Nick Francis faced that question himself.

From the outside, it looked like the job of his dreams. But as the company scaled and took on venture capital, the expectations around growth began to shift. And Nick had to ask himself a question most founders don’t say out loud: Was he still the right leader for Help Scout’s next chapter?

In this episode, Chris Savage talks with Nick about navigating that tension — between growth and craft, scale and vision — and how he ultimately chose to step aside when he realized the company needed something different.

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