Pros
The best thing about working at Overstock are the friends you'll make. Lots of interesting, genuine people with varied interests. Many teams feel like families and many of my dear friends are former Overstock coworkers. I also appreciate that they take chances on good people and big ideas. And the company overall is progressive, tolerant, and multicultural.
Cons
There is very little structure within the departments. Groups and whole departments are restructured several times a year. In five years there, I had 13 different desk locations, 8 different directors, and 7 different managers. At the time of my termination, I didn't have a manager or directors. I didn't have a job description or general process guidelines. Turnover is painfully high.