• Lack of organization. You can get to $5m being only sort of organized. After that, though, you really have to get organized as a VP. Either by yourself, or with a Sales Ops / Marketing Ops / Some Sort of Ops leader under you. Look for dashboards, strong project management, strong pipeline projection after $5m ARR. If you don’t see things getting more organized, that manager can’t scale.
• Inability to hire great Directors / managers under them. By $5m in ARR, managers have to have begun to recruit great managers under them. Not mediocre ones. If you hear a lot of excuses about how their managers perform, it ain’t working. If you see too many weak and inexperienced managers being hired under her/him, it isn’t going to scale.
• Only hire folks that look, act and talk just like them. Hiring your friends, and folks like them, can work OK in the early days, if your friends are pretty good at what you do. But it doesn’t scale. You need a village, a diverse one of all types to scale.
• Fear of Large Numbers. Yes, the number gets bigger every year and every quarter in SaaS. It has to. The top leaders that scale embrace it. If you had a record $1m quarter last year, you may need a $1m month this year. And later, a $1m week. That can be very initimidating to those that can’t scale.
• Resistance to Distributed Teams. Everyone needs a distributed team of some sort to scale past $10m ARR these days. A sales team in Europe, or in a more cost-effective locale. A dev team in Israel. No one can scale in one location anymore.
• Threatens to Quit if You Bring in Her/His Boss. This is a tough one, but the best managers get that if they can’t scale, you’ll need to bring in someone that can. They get it. In fact, they say the same thing to their managers. If by contrast, a VP threatens to quit if you ever bring in a CRO or SVP above them, that’s a sign.

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