I have one primary question that I'm trying to figure out during job interviews. "Will my boss understand what I produce and the difficulty involved in producing it?" if the answer is no, the job is going to suck.
It's not just one level though. You can ask the same about whether your boss's boss will understand, and so on and so forth up the food chain.
The problem with many tech-as-a-cost-center companies is that you will quickly run into a person on that hierarchy who doesn't (often at or near the intersection between tech departments and the profit center business departments).
And if your company wants to "flatten the structure" running into that person is more likely and you will run in to them.
I also have a problem with ex-developers who work their way up the structure with time. Generally they drift away from the tech and what tech takes and end up serving their higher masters. So you end up with someone who thinks they know what it takes but hasn't actually done it for many years. Literally had this again the other day when I gave an estimate for a piece of work one of the devs had done a decent bit of investigation on. Bluntly told that was too much time from someone who had really no much more info than the subject line of the bug report. Of course who had the weight to get their estimate across.....(not me)
I like the rule whoever estimates lowest gets to do it. If you aren't in the running to do it, your estimate doesn't count. It's easy to armchair quarterback if someone else is on the line.
The problem with many tech-as-a-cost-center companies is that you will quickly run into a person on that hierarchy who doesn't (often at or near the intersection between tech departments and the profit center business departments).