When your company outgrows its COO: the $100M to $1B gap

Executive overview

The COO who builds a company to $100M is rarely the right person to scale it to $1B. Cameron Herold shares the story of being fired by his best friend and CEO, Brian, and what it taught him about leadership transitions.

Every senior hire has a shelf life tied to revenue doubles. When the company outgrows the leader, the board and CEO must act — but how it's done matters as much as when.

The entrepreneurial COO and the corporate COO require fundamentally different skill sets.

The firing

• Brian called it at a 7am pre-meeting breakfast, ordering grapefruit instead of eggs benedict — Cameron read the signal the night before
• Brian's words: "You were the right guy to get us to 100 million, but you're not the guy to take us from 100 million to the billion"
• Cameron was replaced by the former president of Starbucks USA, who had run all North American operations
• He was crying so hard Brian drove his car home; it took four years to rebuild trust

The two-doubles rule

• A senior leader can typically carry the company through two doublings of revenue
• Example: a head of marketing hired at $5M can likely perform at $10M and $20M, but not at $40M without significant skill uplift
• Cameron was the last of five leadership team members to be replaced over a six-year period
• He knew he was the wrong person to scale further — his issue was with how it was handled, not the decision itself

How identity compounds the pain

• Cameron had an unhealthy relationship with work: the business was his entire identity
• Losing the role meant losing his sense of self, not just his job
• Brian also struggled — letting go of the person most responsible for getting the company to that point
• The board mismanaged the transition; the decision was right, the execution was not

What good looks like

• Cameron's book The Second in Command covers this explicitly; the final chapter is titled "When the Party's Over"
• Transparency and dignity in the offboarding matter — secrecy and paperwork-flipping signal disrespect
• Despite the rough exit, Cameron was asked to speak at company events four days and four months later — the relationship survived
• Trust was rebuilt partly through Brian's book Willing to Fail, which mentioned Cameron seven or eight times while omitting other leadership team members