Pros
Work life balance is good. Benefits are not bad. Flexible hours.
Cons
I worked for Overstock.com for 3 years. It was one of the worst ran companies I have seen. Software developers are treated as 2nd tier employees. People in IT are often referred to as 'resources' rather than members of a project. They are told what to implement and there is little to no true collaboration between developers and the 'business side' because of power control. Unfortunately a lot of development teams are OK with this because it allows them to put minimal effort in, arriving at 9:30 and leaving at 4:45. There is little to no room for advancement in IT. Ask about it. Communication between teams is near non existent. In fact there exists a certain "if I don't have to tell you I won't" type attitude in near every area of IT. Much of the IT staff is being moved to the Warehouse facilities where the office space is terrible (but they won't show you that during the interview). Most Developers are given 1 box that is a core2duo machine, yes a core2duo!! Two 26 1080p monitors. I have heard it called sweat shop development, thus the terrible hardware provided. They have a 3 year hardware cycle program, but buy low end stuff to start with. The new CTO (as of a year ago) came in because he had been 'successful' with out-sourcing at KPMG. He has started the same sourcing to India at Overstock as well. It is not popular, but he continues to push it through. To summarize, on the surface Overstock seems like a good place to work. But the details show a company that doesn't trust their IT/Development group. Has staff cycling through it in many departments. Overall you will be treated as just a number in the staff. Lastly Amazon is eating Overstock's any potential for growth.