Pros
Guidewire has been an amazing place to work so far - great team in general (with exceptions, see below) especially in Sales Consulting, Services and non-HQ dev offices. Strategy makes sense!
Cons
Development management is very weak and out of touch with what the customers need and what it takes to be successful. This team has been so insular for so long, it has a completely different culture than the other parts of the organization - sales, services and finance have a hard-working, just-get-it-done attitude whereas Foster City Dev seems privileged and focused on personal (ie technical) advancement and not on customer needs. Most developers are only in the office at 10, leave at 6 and spend a lot of time eating the free food while other parts of the company regularly work 12-14 hour days, often in crappy hotels and airports. Most in development, starting at the top, have not bothered to learn anything about the insurance industry and our customers' world.