Pros
There were some brief times in my career there where I wasn't hassled by middle management that were fine.
Cons
Where to start. This is not really a software company, this is a services company that was under distress, saw an opening and became a software company. Because of that, they "lead" almost exclusively from the top down and using fear as a motivator -- think old-school financial industry. There are tons of politics to play if you want to move up (and by that I mean just become another manager) and a very bloated middle management layer that drags the entire effort down. There were times in standup when I would give a complete update, only to have my updated repeated nearly word for word by a middle manager and then be asked "Is that stuff done?". It was maddening. Engineering leadership is all-but-non-existent and the threat that is delivered over and over is that upper management or the CPO or even the CEO "are going to get very involved" if you don't ______. It was said to me dozens of times over my time there. "Rusty (the CEO) has eyes on this" was a common thing to hear, insinuating that if you didn't get it together that upper management was going to drop the hammer. Now I want to be fair, I was sometimes tough to work with and as that pressure and stress would mount, I would get more and more frustrated, and that's definitely on me. I have areas in my work life that need to improve just like everyone else, but I feel I could have been successful there if I would have felt even the least bit supported when I took on or was assigned to a large project rather than hounded and harassed. Without a doubt, Datasite brought out the worst in me.