Pros
I'm a Boomerang (someone who has left Overstock and come back), just like many of the best people I have worked with in Utah. I left because the tech culture was stifling, but came back because a former colleague convinced me that had changed. I have to say I love my new job. I am able to use cutting-edge technologies that allow me to be super-productive. I always loved the fun and diverse culture at Overstock and I'm glad to see those aspects of the company still thriving. While the companies in California pride themselves in their diversity, I'd say Overstock is even more diverse that what I experienced in California in that Overstock embraces even intellectual diversity. I've always loved that Patrick (the CEO) is one of the few outspoken people that is willing to put his money where his mouth is, not because of hopes of some kind of political or other gain, but because he believes it is right.
Cons
We had some recent layoffs and they are a bummer. A few of my friends were affected. It's tough, but it seems that many of the people let go had grown apart from Overstock and it may have been the best thing for all involved. Others were laid off because a huge ramp in hiring and marketing spend did not work out as expected, so the company, unfortunately, had to reset it's bearings. Beyond that, some employees are bothered by the frequent changes in direction, which is a totally valid concern, but it's been the same at any other company I've worked and it honestly stopped bothering me before I even started at Overstock the first time. I am super-optimistic, however, about the new management as they are moving in the direction of customer and data-driven decision making, which I have come to believe is the best way to build and run a business.