Pros
I was a software engineer in Guidewire's product development group. There are a lot of things to recommend Guidewire: Most important, their hiring standards are high, so the people who work there are smart and capable. I learned an incredible amount myself working there. There's little-to-no politics, and little in the way of middle management. The company uses agile development methodologies with an emphasis on automated testing. Code refactoring is common, but there's a safety net of over 20,000 (perhaps 30,000 by now?) unit tests to catch regressions. Speaking of testing, the leadership realizes both the short-term costs and long-term gains of developing thorough automated tests, so time spent developing quality software is not only appreciated but expected and budgeted for. Finally, by and large Guidewire's customers absolutely love the company's products and people. As a result, the company is a real success. The company grew from nothing to become the gorilla in the property & casualty insurance claims software market in a matter of 3-4 years. That growth occurred because the company develops useful, easy-to-use software that delivers real value for its customers in their core operations. With that success under its belt, the company undertook the challenge of developing two new products -- one in policy administration and one in billing -- that seem to be meeting with similar success in the marketplace. I'd be remiss if I didn't also mention the company's core values: integrity, rationality, and collegiality. Unlike other companies I've worked for, Guidewire really lives by their stated values. This starts at the top with the six founders, and pervades the way decisions are made and people treat each other throughout the company. There's also a theme within the company of continuous improvement. Time is taken to solicit everyone's feedback on a regular basis. Although not all ideas can be acted upon, some always are, and that improves things for everyone. Sometimes, ideas are tried and rejected. Because improvement is part of a continuous process, people feel free to experiment and try new things every month or so.
Cons
The biggest downside to working at Guidewire is the domain: insurance software. It's not exactly 3-D graphics or the hottest Silicon Valley technology du jour. Still, from a software engineering perspective, there are definitely some interesting technical problems to solve. I found life within product development to be a bit cliquish. The same small groups seem to break off for lunch every day, and there's little interaction between cross-functional groups. There's not a lot of opportunity for traditional career advancement at Guidewire. At least within product development, the structure is flat and titles aren't all that important. Everyone gets an annual review and salary increase (when merited), but announcements of title promotions are rare. I preferred this approach, but if you care about your title, it may not be the place for you. Developing enterprise software is just plain *hard*. The customers are using such antiquated technology that often they can't articulate what they want. So product managers have the near-impossible job of trying to synthesize many disparate requirements into a single product, and not surprisingly, the first attempt is not always what the customers exactly need. This leads to a non-trivial amount of re-work, which can be frustrating. That said, part of the problem when I was there was that the product requirements identified by product management were often vague, which led to engineers building the wrong thing. (In fairness, this was identified as a problem and steps were being taken to correct it when I left.) Another challenge is integrating the product with each customer's legacy systems, since they typically have many such systems and can't retire them all at once. Integration is a big challenge for product development, but especially for the professional services group. Those folks do an *incredible* job deploying the product under very challenging conditions, all while keeping the customers engaged and happy.
