To answer some of the common questions: My background/speciality is 2-sided marketplaces in the tech world.
I don't think I'm bad at interviewing or come off as an asshole. In the past, I could easily land a new position in a month or so. I know markets change, but I feel that as my career and titles have grown (management and C level and one FAANG tier company on my resume), I find myself being dismissed at the final interview step.
I have had the overqualified theme thrown at me few times. Perhaps I excel at IC interviews, but suck at management tier interviews.
I could downplay my experience. I have to admit, I saw it as a form of dishonestly, initially.
Here is a recent example: My last interview was for a management position at a small startup, with decent funding. During my first meeting with the Head of Engineering, he informed me that he felt I was overqualified, after seeing my resume. It was clear that I had more experience in both depth and breadth than he -- I don't really care, but as someone pointed out below, perhaps that could be seen as a threat. I don't care for office politics, I just wanna get things done.
Another interviewer (different company) informed me that my resume looked as if I were entrepreneurial (as I do have my latest startup listed), and they were worried if I would be satisfied. I tried to allay their fears, but to no avail.
This may not be what the executives want, but they are so detached from hiring that they cannot and will never change it. It just doesn't hurt enough to care because there is an endless supply of average workers.
I am in the same situation and have no idea what to do next.