Pros
I'm a developer. I've worked for 3 companies in the past 3 years. Overstock is most certainly my favorite place so far. It's a fast paced environment with a lot of energy. I feel like the owner really does care about us as individuals. As a developer, there's ALWAYS something to do. There's always a project going on, and that's what interests me. The culture is a "laid back get your work done" culture. At least for my team anyway. That leads me to my next point. Your team is what determines your happiness here. That being said, my advice to those that read this would be: If you don't like your situation. Speak up. A little communication can go a long way. Benefits! Benefits are GREAT! I can't believe the people complaining about our benefits. If you don't think these are great, go take a look at a few other companies out there. You really don't know how good you have it here until you go somewhere else. Believe me, I've been with 3 different companies and these are the best. Could they be better? Of course. But they could definitely be worse. A lot worse. 6% 401k matching is unheard of. Thank you for the generous benefits even though people are still complaining about them.
Cons
Sometimes too fast paced. People will drop hits that "We're losing a bunch of money every day we don't have this feature." and that can put a lo of pressure on you as a developer. If you give a completion date, you'd better have that completed! So just be careful to pad plenty of time for your projects. Being a retail site... Overstock isn't a tech company. So using the latest and greatest is not going to be an option in a lot of cases.