Severe, chronic, almost criminal understaffing. They're trying to compete against larger companies with a skeleton crew and the workload and stress level are off the charts. Every single day you feel like you're skirting the edge of disaster, and nothing ever gets better.
Upper management is cheap, dishonest, erratic, unprofessional and almost comically disorganized. I think they're smart nerds who got picked on a lot and grew up to be frightened, angry and mean. They seem to be unaware of, or unconcerned with, the constant frustration faced by employees and refuse to take responsibility for anything. Their solution to every problem is to "push harder", "dig deeper", "go the extra mile".
Training is minimal and largely irrelevant. Documentation consists of the google and a hit-or-miss wiki. Support policies are ill-defined, usually ex-post-facto and sometimes contradictory. There is no solutions database, no issue tracking, no trends analysis. Admins are constantly re-inventing the wheel.
Back-end infrastructure is held together with chewing gum, velcro, and ebury worms. Like everything else about the place, it was thrown together in great haste and without a plan.
Pay is very low and benefits almost non-existent.
Bottom line, everybody, and I mean everybody, eventually gets fed up and quits.