Pros
Small company with lots of talented individuals, a flat organization, and a culture of trying to delegate power to individual teams. As a model of how to structure a modern engineering organization that can be flexible and responsive to customer needs, Guidewire is a decent example.
Cons
Guidewire investors and executives, like most startups, are greedy. The compensation package is rather week, as are the options offered. Generally speaking, startups offer strong salaries because it is unclear whether the stock will ever have any real value, or even if employment will be assured for long. Guidewire offered rather low salary, especially for a startup, ignoring the risk factor associated with working for a startup, and stock options were pathetic.