Pros
Company has many happy customers and many people enjoy working at Guidewire Work life balance good for development
Cons
Guidewire's technology stack is horribly out of date, the newer version of the software while solving some problems is poorly implemented and development within it is very slow. If you work at Guidewire for any period of time the skills you develop will not be transferable to another employer due to the fact Guidewire has their own language (gosu) which has some interesting features but is only used at Guidewire. They also use their own persistence framework and web ui platform. The web ui platform (PCFs) is one of the weakest areas in the technology stack. This was improved with the latest release but still not something which most devs will enjoy using. The services part of the business has some very dedicated employees but some decisions in the past year including laying off several new PS staff recently hired caused many to question how dedicated the company is to this part of the business. It appears the idea is to outsource as much as this work as possible. The impression was also conveyed internally that PS is more or less a necessary evil and that what the company is really about is selling software. There has been some back peddling on this as of late but the damage was already done in terms of morale of many PS staff. The collegial environment everyone talks about still exists but is definitely waning.