Pros
Exceptionally friendly team of professionals to work with. Everyone really cares about their job and their contribution to make Guidewire a leader in the insurance software space. Guidewire keeps its promises to its customers, so customer satisfaction is very high. The products are stellar and something you can be very proud to sell.
Cons
Management has no formal training running a company of Guidewire's size and it shows. The founders needed to back out in 2008/09 and let more experienced hands guide the ship. The management team is full of political posturing and this effects team performance. Management in the marketing team is especially lacking with poor decision making, lack of follow-through and zero long term strategy. Sales whims drive all marketing efforts so nothing ever feels completed. Moral is very low among the ranks with respect to their view of management.