Pros: Some smart people. Benefits are decent. The company has a good cash balance to burn.

Cons: The company is in the space of providing software to P&C insurers. It has undergone major changes, especially in product development. They wish to accelerate stagnated growth by executing too many things too quickly: SAAS, Cloud, and 3-month release cycles (from 18 months). All recent initiatives are new to the company, which does not have any expertise, experience, or ideas in the technologies they are venturing into. The management is not cognizant of that fact. They need to bring in tech experts from outside. They tried to an extent but are resisted internally by old-timers who do not cooperate with new talent. The middle and first-level management is terrible. They play favorites, manage by bullying, and give bad reviews. Managers thrive by managing up and do not help team members. They take care of themselves first and cover their backs first. As an employee, you are left alone, and you need to fight alone. The other pain points for the company are: the core products are built on monolithic architecture. Competition is catching up fast by providing cheaper and better insurance software. This has sent alarm bells ringing to the top management. The P/E ratio of the stock is 498, which indicates that the company is grossly overvalued. Investors are anticipating higher growth, and the earnings are meager when compared to the stock price. If you are looking to work on exciting applications and cutting-edge technologies, this is not the place to be. But, if you want to play politics, use flattery, work on boring insurance software, and do some minimal work to get through, this maybe the company for you.

Pros: Flexible schedule makes for a good work/life balance. Lots of smart, approachable people that are always willing to lend a hand. Located at the west end of the SM Bridge, the office is quite accessible from the east bay. * Stand-up desks * Powerful development systems: choice of high-end PC or Mac. IT doesn't care if you delete Windows and install Linux. Systems are replaced with an even better one every two years. Outside training and classwork is encouraged and reimbursed. Opportunities to attend conferences are available as well. Good variety of work keeps things interesting, at least in my current role.

Cons: Workspace on the development floor is crowded and sometimes noisy. Proprietary tooling and programming language are not desirable skills outside of Guidewire and thus are not 'resume material'. Once a flat management structure is becoming more hierarchical as the company has grown. I suppose this is inevitable. I've seen quite a few new managers hired from the outside rather than promoted from within the organization.

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 for the 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 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 have 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 parts that work for you, and you don't get, say, sucked into the minutiae 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.