Pros
I worked at the O for 8 years and loved the people I worked with. I worked in the IT organization and got to touch so many parts of the business, and work with many different technologies. Working there truly was fun. If you want to learn a ton, work with energetic, driven people, it is very rewarding from that perspective.
Cons
There is exactly ONE thing that sucks about working at OSTK and it's the "senior" leadership. I won't trot out all the horror stories, but will confirm that other negative reviews of senior leadership are accurate. The main issues are these: - The CEO is distracted by shiny objects and constantly changes course, projects constantly get halted, restarted, and are often abandoned. - There is no institutional memory (largely due to high turnover, as well as constant change in direction) - the same mistakes get repeated over and over again. This is often referred to as "O-volution" by internal employees. - The organization has a highly dysfunctional dynamic where direction is expected to be followed without question. If it's a bad idea, and you don't speak up, you get blamed for not speaking up. If you do speak up, you are "insubordinate." In either case the end result is the same, folks are exited and blamed for the failure of the bad idea. - There is no such thing as an amicable departure. If you resign of your own volition, you are labeled as "couldn't hack it" or similar. If you are let you go, you were "incompetent." - People are regularly promoted far beyond their level of capability. Oddly, when someone fails, it is their fault, instead of management realizing that they made a mistake and promoted someone too quickly. - Fully half the board is OSTK senior leadership. The balance are external patsies who are happy to collect their advisory compensation. They do NOTHING to hold the leadership accountable. - The CEO readily reminds folks that he speaks for 70% of the outstanding shares of the company. Because he is neither accountable to the board, nor to a majority of shareholders, he can and does act completely unchecked. Only the legal department can keep him in the guard rails, and even that only lasts so long before they exit the general counsel and bring in a new one (as has happened in the last year) because he/she isn't "fun" enough.