Pros
Guidewire has been a very satisfying place to work. My co-workers are honest and highly competent; the company takes its promises to customers very seriously; and there is great collaboration between different company functions. There is also excellent communication overall, and the company strategy is straightforward. Work-life balance is up to you, with no face time mandated or expected. The best indicator of the company's quality is that there are so many people who have been with the company for years, including multiple people who left but came back after realizing how good it was.
Cons
The market is obscure; most people think insurance is boring. Compared to Facebook, maybe it is, but arguably it's better to serve a real need than pursue a fad.