Pros
Guidewire is an rare phenomenon not only in Silicon Valley, but in the corporate world overall: a business run with extremely high integrity, passion, and long-term orientation all at the same time. The founders identified a deep (if obscure) market need and pursued it with unwavering focus and humility, quietly designing and building products far better than their competitors (as far as I can tell....). The implementation team is the most competent and selflessly committed I've seen in my long career in IT. The engineering organization is utterly free of the dysfunction and cynicism I'm so used to seeing in Silicon Valley. And the management team is unfailingly transparent with information to all employees, warts and all, treating its workforce as it should be: as highly skilled colleagues in a long-term endeavor, not as fungible inputs in a machine. It's gratifying to work for a place with a such bright prospects, but also so steady and rational a plan and such honesty. I just hope it keeps it up.....but given how many co-workers I see who have stayed for multiple years, through thick and thin, I'm very optimistic.
Cons
This is not Google or Facebook or Twitter. If you're after the sexy aspects of what those companies are said to offer (massages, free sushi lunches, all-night coding parties, whatever), you're not going to find it here. Nor will you retire a multi-millionaire with your stock options. The benefits are average. Also, HR is pretty amateur.