Pros
Guidewire is a committed company who genuinely wants to help the insurance industry by providing the best software and help its customers to be successful worldwide. This is a growing company whose core values are not simply just marketing speeches but can be seen in its managers actions and it reflects in the positive attitude of our colleagues. With the Guidewire employees I worked with, I can say that their skill level is very strong, they are all friendly and very keep to help you, which helps you to learn more on Guidewire products or even on other technologies. I can see some clear opportunities to grow in this company, and although I have to admit that a couple of years ago, a career path was not clear, I think it is well addressed now (in both scenario of staying in the same department or going to another one). This company even helped me to move to another country, keeping my job, to follow my partner.
Cons
There are very few down sides with Guidewire. One problem I can think of is finding candidates to join the company. As we want to keen working with the best colleagues, it may from time to time be hard to find someone matching such standards, but we always ends up with finding one.