Management is awful. Priorities change almost constantly - and not just in small adjustments. Product teams are terrible at taking input from other parts of the org and continue to make wild assumptions about what they should be doing, often resulting in spending lots of time on features, upgrades, or new products that flop. Every once in a while something makes it out that is really good, but that's the exception. The rest of the org gets hamstrung by constantly adjusting to these changes, and tons and tons of time and energy get lost working on things that never see the light of day, or get delayed for long periods of time. In fact, assumptions is a good word for the problems overall. Here's a typical pattern: assumptions made by upper management about the state of affairs. Other parts of the org try to explain why those assumptions are wrong, management doesn't listen, and moves forward with a plan that fails. The people who tried to push back on the plan because they thought the assumptions were wrong then get grilled about why they allowed management to proceed with their faulty assumptions. It's insane.
If that weren't enough, the finance department is absolutely insane to deal with. They view their responsibility to be extremely rigid and look for any and all opportunities to deny requests for money, rather than thinking of themselves as trying to empower employees, departments and parts of the company to be able to succeed. Even simple and small requests become battlefields.
This is made even worse by the fact that the in-house legal is above reproach because she is the wife of the CEO. So requests that can be very important will simply die if you can't get any traction with legal or finance - and that ends up being most of the time. This also means that these kinds of requests, which should never have to go in front of the CEO, end up being raised to that level much more often when people really believe they need something, which is just a messy way for that to operate in general, and makes teams feel totally disenfranchised and like they have to complain a ton to get anything they need.
The CEO is a seemingly nice guy, but there's no sense of vision anymore, and he isn't delivering the kind of leadership the company needs right now, particularly product leadership, or at least the ability to make big decisions and stick with them.
