Pros
In 25 plus years of working in tech, I can honestly say this is the first company I've worked for where I know its core values (collegiality, rationality, integrity) and believe that management and staff alike abide by them. I know it sounds corny, but we are collegial to the max. You never hear anyone say "that's not my job." I also fully trust our executive team. Marcus, the CEO, is brilliant and definitely a leader with integrity. We've had some instances where a person in a manager role wasn't doing a great job. In most companies, that person would simply be let go. At Guidewire, I know of a couple of cases where former managers were invited to step into individual contributor roles instead of leaving the company. I really value this flexibility.
Cons
I can't think of many cons. Sometimes Guidewire is slow to let someone go who isn't doing his/her job well and is not a good fit for the company. On a minor note, I disapprove of our jury duty policy: we're given just 3 days reimbursement for jury duty. I feel this discourages employees from doing their civic duty.