Pros
For the insurance industry the company does appear to have a desirable product.
Cons
Internally, in professional services the company is set up so that an employee's ability to get reimbursed for business expenses may depend on the clients willingness to pay. Also, for a company of this size, the administrative functions, like payroll are a single individual. Low quality control in payroll means a huge surprise tax bill at the end of the year for professional services folks as we can work all over the US and abroad. How many 1,2, or 10k+ suprise tax bills would it take before you got fed up? That should be a question you ask yourself before joining because this is a common problem and most people do not have a spare 10k sitting around to pay because Guidewire made an accounting mistake. This is just an example of some of the things about this company that makes it a miserable experience.