Pros
The work is interesting and exciting, but I would be lying if I said every days is a blast. The market is not always moving, and thus, the work is sometimes a little bit boring. But, the people make coming into work actually enjoyable. The people you work with here are people that will become real friends, both in the office and out of the office. I have friends who have left here that I genuinely still keep in touch with. I don't know what it is, but this place attracts good people, not just smart, but actually GOOD people.
In addition, PEAK6 is constantly trying new things both in and outside of it's main trading business. Sure, they are random, but its super cool when your company has a game playing on the wall and you own the team playing, or when you ask to do some work for a new acquisition, and you actually get to. The place has owned everything from hockey teams to dating sites.
Work-life balance also awesome. In trading, you get in around 7-7:30, and leave by 5 with few exceptions. In tech, you probably get in by 9, and leave by 7-8. Granted there are days when you have to work longer, but for pay with bonus, people don't realize how nice the work life balance is considering pay.
Final major pro, the structure is relatively flat, so if you are willing to take initiative and work hard, you do get noticed. People who "buy-in" to the process and are willing to do what it takes to add value are quickly noticed. Promotions don't really work the same why as other companies. You don't get promoted after a set number of years, rather, after the training program, your career is what you make of it.
Cons
Upper Management sometimes struggles with transparency, but I will say that they do legitimately make an effort to fix it. Pay is also a bit of an enigma sometimes, but they do take care of you in the end. There are a few people here who have been here a long time that are probably given a bit too much leeway.
They often over correct when something goes wrong, to the extent where they are wasting resources.