Pros
Health benefits are OK It is a great place if you are a ski bum or if you like hiking the state of Utah, or simply because you have a higher reason not to leave the state of Utah. If you are good at selling ideas that sound good in meetings and love to have meetings from 8am to 6pm, this is the place for you. If you are crafty enough to arrange your work schedule around meetings, you can actually move from one meeting to another for a whole week, without actually performing any real job as long as you talk your way around the great projects or ideas that should be implemented and take down any new initiatives or real work done by others. Align yourself with the VP of Merch/marketing and you are done and don't ever go against any of the buyers.
Cons
Toxic work environment, you can actually spent days without talking to anyone. No vision of the future at the leadership level. Every day there is a Fire drill kind of environment, where the only thing you do is take out fires (problems) and being careful not to be blamed for the causes of the problem. Patrick Byrne made a great idea a reality, sadly most of his time, ideas and money are spent in fighting everybody else with lawsuits (wallstreet, hedge funds, gary weiss,banks etc) and talking about naked short selling, which is in fact a problem, but not the cause of Overstock's stock price decline. So the company is headless in terms of direction and lacks vision of the future. Retention rate of employees is very low, the average time a person stays at Overstock is close to 1 year. There is no open communication channel from lower to upper management levels, last initiative was to set up a web interface to allow employees to voice their ideas, but the qualification process of the ideas is in the hands of the same people that truncate the communication to the decision person (Patrick Byrne). Great place if you love to spend your time in Facebook and Youtube, just make sure you have one of those 3M screen protectors, so no one can see from the side what you are doing. No retention strategy for talented employees.