Pros
The hiring process is very stringent and strenuous, but the benefit of that is that the people who end up working with Guidewire are all very talented and genuinely great folk. You are given responsibility over important tasks as soon as you complete the training process (which is extensive). The company strive to make a great product and there seems to be a never-ending effort to make improvements in every area possible. No matter how high up in the company some people are, you actually feel comfortable talking to them and voicing your opinion on some things. At our last event in San Mateo, myself and some colleagues who only started a month previously were in a casual conversation with the vice-president of the company and he seemed genuinely interested in being there talking to us. No expense was spared in the office. You have a top-of-the-line computer with two large monitors, a comfortable chair and plenty of closed spaces should you need some quiet time. If you need a few minutes of downtime, there is a pool table, foosball table, xbox consoles and even beer in the press for our Thirsty Thursdays. It really has a startup feel even though the company was founded over 10 years ago and probably has 1500+ employees now.
Cons
The salary is definitely lower than other companies offered me, though I did get RSUs which ensured it wasn't a dealbreaker. In order to keep hiring the best possible candidates and keep hold of talented employees, the base salary will probably have to be looked at though. You can end up working on a project for clients who make it very difficuly to do your job as well as possible. This is more from a technical side than a personal side. Things like overly complex security procedures, slow laptops, virtual machines, among others can really affect your productivity. This is not really a fault of Guidewire though, just something to bear in mind. Honestly, there aren't many other negatives. It really is that good to work here.