Pros
When I interviewed, more than one person referenced the company values (Collegiality, Rationality, Integrity) as a great part about working here. I thought it was a strange thing to mention - who actually takes those HR slides seriously? But they really do here. It wasn't a line. Basically, it boils down to be respectful, be honest, and listen to reason over seniority or politics. Surprisingly refreshing and transparent. I've been here less than a year, and I already feel like an integral part of the team. I've gotten many more responsibilities than at my previous job, and I have a great manager who I trust. On the whole, I feel happy and motivated coming into work every day.
Cons
Working on insurance software is about as unglamorous as you can get, especially in a Silicon Valley world that is more excited about the next iPhone app than anything else. It can be hard to explain what to do, and some of the problems can be very challenging to wrap your head around (workers compensation, anyone) Benefits are solid, but not amazing. If you like the idea of free perks like laundry service or free everything, this is not the place for you. Guidewire makes no secret of prioritizing their budget. Some growing pains of a rapidly expanding, recently public company. There is an old guard who has a harder time with it especially. The upside is, of course, that it is successful and growing.