Pros
Many congenial, intelligent people who want to make things better. The core platform is finally moving to a contemporary cloud architecture using modern tooling. It's a profitable market. The company is riding past success and should be able to continue doing that until it completes the transition from its monolithic "architecture" to the cloud.
Cons
There's very low energy here. It was jarring when I started, then I got used to it, and when I started with my new job I was immediately reminded and refreshed with how exciting a company should be in tech. How Guidewire can sedate this big of a group of people is "impressive". Guidewire has a very one-sided political atmosphere. It's obnoxiously Leftist. Those of us who might have different views (or might not want politics discussed at work) have to grin and bear it. Middle- and some upper-management are incredibly arrogant. They did a good job making Guidewire successful in the past, but they were somehow blindsided by the cloud and/or unable to pivot until new blood came in. That same cabal is insular and if you're not an insider you're nothing. It's very much a 9-5 atmosphere. Innovation is very low. Nearly all energy is spent on cloud infrastructure and very little on innovation. And it's not the industry: there are myriad InsurTechs building really compelling businesses and technology. Low innovation is a Guidewire attribute.
