Pros
Where to start. This place is awesome. Let me first start off by sharing a very common interaction as a new employee here, when speaking to a veteran employee. When asked how I'm liking Guidewire and all that jazz, my response was always a jovial "it's great! I can't believe how awesome this place is". Now, usually you'll get an eye roll, or an empty response from the veteran, followed by a generic Welcome Aboard!....Not here. People that have been here 5, even 10 years react the same way. They are still SO excited to work here. They have pride in the organization, and are proud to be apart of something so special, and so great. I am lucky enough to work out of the Edina office, just outside Minneapolis. It's almost exclusively Sales reps, Sales ops, and management here, but we're a tight knit group. Everyone is so down to earth and welcoming. The entire company has a sort of 'common sense' management style, where there aren't many times where you think to yourself, "why are we doing it this way?". Coming from a giant tech conglomerate, Guidewire's startup feel and culture really make you feel invested in the company, and that you are an integral part of the organization, and all of it's success. We have one of the most brilliant and down to earth CEO's you can find, and the people they chose to put in management, in my limited interactions, have all been tremendous individuals who all bring different skills to the table. I wouldn't hesitate to recommend this company to any motivated and passionate professional.
Cons
After 90 days of employment, I have yet to find a 'con' that is worth complaining about. It's a great place, where your determination, motivation, and drive can take you very far.