Pros
There were some positives while working at Guidewire. It has a very laid back atmosphere in the open space office. I really enjoyed working with my project team who I will always remember and would love to rob some of them to my next place of work! The majority of people in general. You have the opportunity to work from home to allow for outside work situations that inevitably arise. Breaks aren't limited to just getting a cup of coffee from the kitchen, you have pool tables, ps4 and fussball to enjoy with your coffee! I'd recommend Guidewire to people who are coming out of college and want an easier start to life. There is a pretty strict path you follow for ~3.5 years until you can branch off into "Architect" (buzzword which the work doesn't match title) role or continue being a consultant. All in all, I found it a very cushy job.
Cons
This could get very long but there is a reason I am leaving after 6 months. There is no challenge to being a consultant here. At the beginning you sit through 3 months of mind numbing training for the different centers that make up the product (Policy, Claim and Billing) and then take a bizarre exam of no meaning which if you pass (85% or higher) you then do a small assignment with a trainer who is somewhere else in the world that you speak to for 10minutes every day and finally whom you'll do a demo to at the end. I found it the biggest waste of time. It actually prevents original ways of solving problems as Guidewire seem to think they have a best way of doing things where you have to work around their spaghetti code. I believe if they actually invested time and ran (and understood) a stress test, they'd see how inefficient and slow their centers are (obvious costly code ran multiple times for no reason can be found from just debugging). There is also no access to unit tests for the OOTB code so good luck finding regressions without strenuous manual testing. There's also a lot of bugs in the OOTB which is embarrassing and will always be a hindrance to the company moving forward. Guidewire doesn't do constant releases but instead patches, again a hindrance. On my first (and only) project, I experienced a significant amount of downtime where I could sit around for a couple of days clawing for work to come through which is not easy when your client and the project lead is 5 hours behind. This may have been a result from actually having 3 years experience of being a Java software developer that I completed the work a bit quicker than expected but it was very frustrating. It was coined to me that the next project won't be the same but having spoken to numerous people there, the stories only got worse. Next is the money. Straight out of college you'll probably get the base salary of 30k or something (I don't want to be mean but if you're coming from a top college you should be starting on 33-35k), but if you have experience you'd want to be a good negotiator which I am sadly not. They give you this sense of belief that shares make up for the crappy salary by throwing handsome figures at you. Salary is far from competitive (14k increase to my next job) but the benefits are competitive. I should note, they have changed how stock options are now handed out to newcomers so this benefit is not as good as it was. Office is pretty ugly, you wouldn't feel proud bringing someone into the place. There's a lot of managers, some bluffers! To summarise, I would think this is a good place to start your career, get a feel for what is like working in an Agile world, how releases work, taking ownership for code, etc. Or if you have experience and are coming from a stressful/demanding job, this will do as a between job.