Completely unattainable goals. It's either runaway optimism or just extreme pressure from the board, but a good year is hitting 40% of goal. Forget getting your bonus.
You run the extreme risk of being laid off without warning. It's a pattern there, people get laid off without knowing why. Has happened to multiple people in multiple departments. Multiple rounds of layoffs in addition.
Product is way behind the times. It's slow, cumbersome, and lacks key features. Yet the CEO acts like it's the silver bullet for all back office problems. Don't believe me? Ask the customers.
Marketing is directionless. Every good idea is behind layers of red tape, so necessary updates aren't made. Very hard to get anything done.
It's a hard job. If you apply, make sure you understand what you're getting into.