Pros
Guidewire did a lot of things right to establish a strong market position. It enabled the company to start a pivot (which shouldn't have been necessary and is not yet complete) without losing too much business or share. The new CEO seems like a really strong contributor and I have confidence he'll have great positive impact on the company.
Cons
The company has a history of poor software engineering. It got deals done - which is great - but without the discipline to avoid custom implementations and unnecessary rework. It is a decade late getting to the cloud, and it's taking a lot of effort to fix the poor implementations of the past. The internal politics here is pathetic. The company claims that it's internal culture is great, but it's one of the more negative groups I've experienced. There's a clique of Guidewire veterans in the product development division (engineering, product management, QA, docs, etc) who are the very people responsible for the many poor product and development decisions of the past. These individuals strut around with an obnoxious arrogance and cluelessness of what they've done, and they keep "outsiders" at bay. The new head of the division is competent, but equally arrogant. He gets accolades but has yet to deliver more than routine updates to the old products. The important infrastructure changes he initiated have yet to be released and it's my opinion that's due to poor management throughout the middle management tier.