Pros
Overstock employs some of the best, brightest people in the entry to middle-management positions. While working at Overstock I made several lasting friendships and met so many great people. Overstock is a great stepping stone job.
Cons
Nepotism runs rampant like I never imagined possible. There are a handful of people who make the decisions for the company and getting on their good side is the only way to move up in the company. However, even that doesn't guarantee longevity. If you stop being a yes-man or fail to execute something in a way that the exec had in mind with little to no guidance or explanation given then chances are they'll find a reason to fire you. "Make it work or your fired" without clarification on what "it" is was a common management tactic. Which is a shame, because it could be an amazing place to work.