Pros
I have worked in the enterprise technology sector for 20 years this fall, and Guidewire has the most explicit commitment to humility I have ever seen. Partly because their target market is so risk averse, partly because the sales cycle is so long and the account management has to be so strategic, Guidewire has the most thoughtful, careful and consistently successful approach to software I have experienced yet. To echo what others have said 1. People are just plain good at what they do. Really good. 2. In addition to being smart, people are humble. Leads to a low BS, highly collaborative culture. 3. Management cares about your life and the balancing act between home and work.
Cons
Serious title deflation. Most of the Managers here would be Directors elsewhere, and the Directors, VPs. You will be well paid and well respected, you will be given great responsibility-- and then be offered the most modest and junior title you've held in a decade.