Pros
Overstock is the last of a dying breed. It is the last broad-line etailer left that makes all of its money from e-commerce. While Ebay and Amazon make most of their profits from enterprise products, Overstock soldiers along making every dollar selling sheets, shoes and DVDs. As a result, you have to be good at etail because that's all there is at Overstock. And there are / were some good employees that know it well. Working at Overstock will help you learn ecommerce inside and out.
Cons
Senior Management - CEO and current President - have no interest in building a profitable business. There is a strange desire to follow a dream that will never come to fruition. Unlike Amazon's CEO, who is an engineer and a "doer", Overstock CEO is a philosopher, so majority of strategy or ideas follow the path of philosophy - words, but no clear actions. There is no real strategy, no real interest in pursuing a clear path to long-term profitability. The goal is to play in any sandbox the CEO is interested in - its a fun game for him, and he doesn't care because he has inherited hundreds of millions from his father. Executives who oppose this approach are terminated or pushed out. During my time there I saw some of the best leaders and executives walked out the door for opposing the CEO in even the most subtle ways. Pay is relatively low - it is Utah, so people are willing to take a cut to work there. Work-life balance is amazing - no reason to work hard when there is not real incentive to deliver results, or your own projects are killed. Politics are rampant - but they are easy to understand - they all center around doing exactly what the CEO and President say, no matter how inane.