Pros
People are pretty uniformly nice. Good development environment if you're into Agile. Very test-based as well. It's very much a 9-5 type of environment; people aren't staying into the evenings or coming in on weekends.
Cons
The "technical floor" work environment is extremely open and consists almost entirely of long tables with no walls. While work from home is reasonably generous, it's also needed if you want to focus without likely interruption. Buy a really good set of ear covering headphones. There's definitely a "Guidewire kool-aid" among people who really love the company. But there isn't really a "Guidewire culture" outside of work elements. It's a job, no more, no less. The preceding is what I meant in the headline. If what you want is a basic job, with no significant pressure if you do reasonable work, but nothing particularly interesting about your workplace, Guidewire is a good choice. If you want something more, or generally like a traditional startup feeling/vibe, it isn't. Company needs to understand the difference between "frugal" and "cheap". Given current size (500+, not the listed 50-150 here), longevity, and revenue stream, there's really no excuse for all of no 401K match, insurance co-pays, only 3 sick days a year, and a $40/day meals per dium for travel.