Pros
Overstock looks great on paper -- and some, but not all, of the perks do work out. Developers and other tech professionals start with 15 days of paid time off per year, in addition to 8 holidays and one floating holiday. On some teams, working from home occasionally is a viable option.
Cons
Beware what you hear from recruiters and interviewers. Standard, or even conventional, ways to move from team to team do no exist. There is a site where you can ask the CEO questions, but it will politely correct you that he has "gone fishing" and will be too busy to answer any questions for months on end. New hires are assigned to teams often at the very last minute, meaning any indication from the interview is likely incorrect. Our technology and applications drain the life from developers. Every application is labeled legacy. Methods deprecated ten years ago will never be finally removed. No one advocates for the improvement of our systems or processes; thus, developers with even minimal amounts of pride in their work inevitably leave. Established technologies are dismissed in favor of quirky out-dated in house solutions. The organization lacks direction. One minute, we can't hire fast enough; the next, we're laying off dozens of employees. At company meetings, the software architects laugh at remarks from the CEO and president about the future of our technology. The leadership loves to view themselves as leaders of an innovative "tech company", but do not possess any technical expertise themselves, nor do they seek the advise of the trusted employees within the company. The bleak view from here will not relent anytime soon.