This word isn't common in software because we are all operators, but if you're writing for an audience that includes investors and consultants, using the word operator to denote that you're actually executing (as opposed to investing/consulting) is pretty common.

Not a red flag, just different vocabulary for a different audience.

I enjoyed replacing it with “worker bee” in my head, at least.

I think his use of operator is a result of his VC background where it is a common term. In that context it is used to distinguish b/w investors that come from a finance background vs a startup background. Or to describe people that transition from being an investor in a company/board member to working at the company directly.

Being an operator just means you're executing. If you're a good operator, you're good at executing on ideas/projects/whatever.

Why?