Incredibly short-sighted leadership. 3 CEOs in 4 years has resulted in top priorities one quarter being killed off the next quarter. Lots of reactivity, rather than pro-activeness. Massive eng initiatives (see: DCM, MLP) fail over and over before sr leadership finally learns the lesson that their employees have already been telling them (we should be on a unified stack; we should understand how our existing product actually works). Burnout is real, and leadership would rather let people churn than try to fix the culture. Good performance isn't rewarded, my and my teams' total comp has been either equal or REDUCED year over year, even after my team delivered measurably quality and valuable work quarter after quarter.
Lots of senior leadership comes from startups and have never operated at orgs this size, and it shows. If you're not "in the in-group" (aka from Handy), you're probably not going to move up. Internal growth is a rarity; backfills and new roles are usually filled via outside hires.