Pros
While there is no perfect company, Guidewire is about as close as you are going to get. We run into challenges like every company does--some internal, some external. But when your entire organization, not just the executives, are rational and highly intelligent, it makes solving those problems a lot easier and faster. The long-term trajectory of Guidewire is amazingly strong and senior leadership, from the person I report to all they way to our CEO, is truly exceptional. The group consists of quite possibly the most humble, rational group of leaders that could be collected. This is a unique place to work.
Cons
It's tough to articulate cons that are unique to Guidewire. For example, if you are in a role at Guidewire that requires heavy travel, does that force you to constantly plan and adjust to achieve work-life balance? Of course--but that's true of any company.