Pros
There is a lot of freedom to implement new technologies as Guidewire seeks to become more than just a software product and more of a platform. This is good and it shows in the types of hiring they have been moving towards. Benefits are excellent especially if you're young since they offer an HSA and Roth 401k, both excellent tax choices along with several decent perks such as reduced price on movie tickets and theme parks. The company is growing quickly and management is onboard with what it takes to be competitive while this growth happens by planning transparent quarterly meetings.
Cons
Still a lot of cruft from old "NIH" systems. They are progressing in adopting external technologies such as cloud and open source frameworks so this will take some time. Everyone seems onboard though, which helps.