Pros
Healthy culture, great benefits, the working mode is hybrid, flexible working hours, friendly colleagues, and supportive superiors. Essentially, you will feel very comfortable and productive working in Guidewire, your main focus will be on the work and the development for yourself and your team. Whenever there is a blocker, your superior or anyone are always reachable for helps. From a software engineering perspective, Guidewire adopts the best possible practices and technologies to their products and developments, essentially you will learn and find many things that are rarely needed in a smaller size company.
Cons
Many internal tools in Guidewire are meant for internal-use, your experience of using those tools may not be relevant when searching for the next career opportunity. Guidewire ecosystem is enormous and diverse, it is not easy to pick up everything during your first 6 months in the company, especially when you are responsible for developing and shipping the product to the customer. The career opportunity to advance can be competitive because the pool is simply too small for so many candidates who are generally good and equally qualified.