Pros
Cool corporate campus, fun monthly events, good insurance options, generous 401k match, on-site health clinic & daycare, and a reasonably priced cafeteria with tasty food.
Cons
Nepotism really is as rampant as other reviewers say. It's leadership roulette, some seem capable and confident while others... are less so. Building trust in leadership is a constant, company-wide struggle. Direct management is also a toss-up. In my time at Overstock, I had managers that were empowering and trusting as well as managers that seemed to enjoy belittling, shaming, and criticizing others. A lot still needs to be done to improve psychological safety in the workplace. Early on, compensation was fair and competitive, but Overstock has developed a habit of permanently increasing job responsibilities without increasing pay. It's easy to get stuck in a dead-end position. Not enough opportunities for advancement. There's a perception that management's only willing to create new positions for friends.