Pros
The workplace has an impressive range of diversity in terms of race, gender, sexual-orientation, age, nationality, and politics. What's really exciting is that this seems to be self-selecting -- new hire Work environment has humane schedule/hours -- full-time means 40 hours. Subject to your team's habits, the company is tolerant of people who want to work slightly off-peak hours (to avoid rush-hour traffic) or telecommute a day a week. Management does a good job of planning release dates and feature sets so that the slog up to a deadline isn't a death march of late nights and/or lost weekends. Relative to many tech companies, Guidewire's products have an extremely long horizon (read: a decade or longer) because the products are used by large insurers who move very deliberately. Consequently, if you spend time/energy building something, you will almost certainly have the satisfaction of seeing it ship to customers, because there's almost certainly an actual customer that has asked for it and is eager to use it. Turnover is low, and my experience speaking with employees that have exited since I joined is that they seem to leave for positive reasons. Largely, they told me they were looking for something categorically different (excitement of a startup, early retirement, unusual opportunity elsewhere, going back to school, etc.), not leaving out of dissatisfaction. Communication skills and collegiality (in terms of behavior) are highly valued. Since virtually everything ships and has a long life in maintenance, teams spend a slightly greater-than-industry-average amount of time discussing designs and doing future planning. (The result is that legacy code is surprisingly easy to maintain.) Guidewire is a genuinely modern approach to the insurance industry...no 20th-century albatrosses here. Development work is done using recently stable (and sometimes slightly leading-edge) tools. For those who like to play on the bleeding edge, the company holds regular hackathons where those flights of fancy are encouraged. Tech talks are a regular part of the dev culture.
Cons
Guidewire's customers value stability, so if you enjoy life on the bleeding edge of the technology curve, know that it can be difficult to include new, cutting-edge technologies in actual products until it has demonstrated success stories elsewhere. Turnover has been low, and growth has been gradual/metered, which means that the average tenure of employees at Guidewire seems to be significantly higher than at other development organizations, which can be frustrating to newer hires. Close working relationships have been established over the last decade, and it can take longer for new employees to earn parity (in terms of trust and credibility) than it would at another company with less history (or more turnover). Those expecting to quickly climb a corporate ladder should be aware that the kind of meritocracy practiced at Guidewire highly values a long-track record of successes at the company, and it takes time to build up a portfolio that competes with the unusually large number of employees that have been at the company for long enough to have an impressive collection of successfully-completed projects under their belts. As with *all* successful companies of this age, there are a small number of curmudgeons that have survived from the early days of the company. While not ideal, it's fairly rare, mostly harmless, and says something about the loyalty of the company to those who stuck it out through the uncertain days when the company was a startup. Still, those who have a low tolerance for that kind of thing and are considering a job offer might want to bluntly ask if there are any such personalities on the team where they would work.