This is my complaint with "cyber insurance". Companies spending money on insurance premiums and checklists for the insurance company rather than spending money on security.

Yep. My experience as well. Once a place starts doing useless box checking stuff like SOC2 it’s time to find a new job or switch vendors.

Positive indicators would be talking to employees and getting an idea of organizational clue level. There are no shortcuts here I’ve ever found beyond doing this sort of old fashioned “know your vendor” style work.