> 2. You held very senior positions. I think a lot of people don't like hiring people that were more senior than them. So that CTO is being held as a negative. They are not saying "Hey I get the experience of an EM and a CTO in a Senior Engineer for a bargain salary", they are worried you will overshadow them. This is sub optimal behavior for companies.

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Not only is there the overshadow worry, but there's the overqualified for the position.

You were CTO once, and now you're a IC again... are you looking for a CTO position still?

I had an experience (post dot com crash) where the team hired a senior engineer... who left the team within a year to be an engineering manager somewhere else in the company and our team was back to interviewing for the position again.

From our team's perspective we wasted the time interviewing and onboarding a person when they job-hopped (even within the company) in under a year. Despite being qualified as a senior engineer it wasn't what they wanted to do.

To that end, overly qualified candidates are similarly risky to hire as under qualified ones.

I've also been in situations where someone in a senior or management position is hired with previous Big Tech or startup experience and tries to make the regional retail company's internals into a Big Tech engineering department which ended poorly for everyone involved.

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To your third point, the desire to stay on the coasts and around Big Tech companies is also a thing. Being willing to move to and within the midwestern states (some companies have return to office... others don't want to create a tax nexus in another state - if you don't hire anyone in California or Colorado you don't have to follow those laws... so hire everyone in one state and only deal with one state's payroll tax and insurance options).