Cameron HeroldFounder of the COO Alliance & Invest In Your Leaders Training

Why Your Best Leaders Fail as You Scale

1 May 2026 · 1 min

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Cameron Herold explains why strong leaders typically fail after two revenue doublings. A head of marketing might handle $2M to $8M growth but struggle at $8M to $16M because the complexity, team size, and budget demands exceed their skill set. Without deliberate development, these leaders get outgrown as companies scale.

Chapters

Do you know that most mid to senior level people can only stay in their role for 2 doubles of revenue? And by the time you try to get to the third double, they don't have the skill set or the confidence to do their job. But here's what I mean by that. Let's say that you have the head of marketing and you're a $2 million company. When you get to $4 million, your head of marketing can probably do the job. When you get to $8 million, they can probably do the job, but they're probably not able to run it at a $16 million size. There's too many employees. The complexities are different. Too many freelancers. There's too much— the budget's too big. They just don't have that skill set. So unless you grow their skills, you're going to be putting them out of, out of a job. Those numbers tend to add up. Every time I talk to leaders of bigger companies, it tends to be 3 doubles or 1 triple. If you go from $3 million to $9 million, they can do it. But from $9 million to $27 million, they can't do it anymore.