Pros
Guidewire has been a great place to work. Before it went public, the compensation package was great, most who joined before the IPO got a pretty good deal. It's still a really nice place to work. The focus on rationality, integrity, and collegiality is really rewarding. I like feeling empowered/encouraged to help our customers succeed. It's also a rewarding industry: we do something that matters to the social fabric, insurance is a key part of encouraging the kind of risk taking that makes America great. There is room to make a difference. The company is now an entrenched player, and will be stable for decades to come.
Cons
The only real con is that pay and other comp factors are now lagging the industry. That's partly made up for by some of the fringe benefits (e.g. no death marches), but there are a growing number of places where you can get those fringe benefits _and_ a stronger pay package. Guidewire has unfortunately also taken a path of overrewarding at the top. People who have almost nothing to do with the success of the company are getting massive stock packages, while the people who build the products that make all the money get very little.