"We Had to Bet the Company" — Nick Francis on Reinventing Help Scout”

What happens when your values clash with your business model—and the market starts to move without you? Nick Francis, CEO and co-founder of Help Scout, faced that exact moment. In this episode, Nick shares how he made the bold decision to kill a pricing model that had driven over a decade of growth, and how he rebuilt the company from the inside out. From AI disruption and shifting customer behavior to boardroom tension and strategic reinvention, this is a raw, honest look at what it takes to bet the company and come out stronger.

If you’re a founder, CEO, or operator facing hard truths—this one’s for you.

Timestamps:

• 02:10 – The moment everything changed: COVID, capital, and chaos in SaaS

• 06:40 – “This is over”: When Nick saw the model breaking

• 12:55 – Values vs. pricing: Why per-seat didn’t align anymore

• 21:45 – The 3-month rule and building a usage-based model

• 30:10 – Selling the change: customer pitches, board pushback, and conviction

• 42:35 – Strategy ≠ execution: Rediscovering differentiation