A truly great engineering org.
Pros
I recently left Guidewire after nearly a decade for a very large company, for career-development and salary reasons. Guidewire's core engineering culture remains exceptional and I would not hesitate to work for them again in an engineering role. Despite the kool-aid at the larger company I now work at, Guidewire remains the place where I was around the largest proportion of brilliant people, and even more importantly, with the fewest jerks and egotists. Guidewire engineering has a tremendous emphasis on craftsmanship and quality. They also have huge flexibility with workstyle and time off, realistic deadlines -- no death-marches at release time -- and the company as a whole takes the customer focus and value "integrity" very seriously. They rarely over-promise, and they will do what it takes to make things right when something goes wrong.
Cons
There are three main concerns to engineering org: First, there have been some growing pains and since my departure there is a new SVP, so there is uncertainty about whether they'll be able to keep the culture intact while keeping up engineering velocity up at the same time. I think the outlook is positive, but having moved on I can't say for certain firsthand. Second, with the "arms race" in salaries (and other compensation) between large employers around here, it seems like Guidewire has opted out - at least for old timers who've built seniority on the job. The same could be said about "perks" and other benefits although my own philosophy on such things is that I'd rather have a higher salary and fewer frills. Lastly, for some people, insurance can be an inherently dull subject. Technical management mostly does a good job of trying to keep the focus on quality and process and for many people that's enough to keep things interesting -- there's a good division of work so that you can focus on what parts work for you, and you don't get say, sucked into the minutia of insurance specific business logic or financials if you're not so inclined. I have a much more limited sense of the company outside engineering these days, but as of a few years ago when I worked more closely with other divisions things were very mixed depending on which.
