Pros
Opportunity to grow in your career if you want it. Not a lot of red-tape or unnecessary process. Operates more like a start-up, you are given a lot of autonomy to solve the problems you are facing. You can learn a lot and gain exposure to areas of the business that wouldn't normally be in your scope at a large company. Management is supportive and you are given a lot of trust as long as you do the right thing. Amazing perks, excellent work-life balance, and some very smart people that you get to learn from. As long as you are doing what is right for the business and working hard, you will love working for Overstock.
Cons
There are some people that have been given opportunities because they have been around since the beginning, but they are not effective and have no other business perspective. Departments could be better are cross-collaboration to minimize duplicate efforts.