Pros
Unlimited PTO is awesome. Managers are really flexible about working from home. This is a good place to start your career; college grads are given great learning opportunities based on what I've seen. Just don't stay here.
Cons
Middle managers often feel like they have no idea what they're doing and are determined that they're right, even when they clearly aren't. The executives are very disconnected from basically everyone else. Insurity has frequent rounds of layoffs as they are becoming more and more determined to outsource, and these layoffs are making it increasingly difficult for everyone in the Hartford office to do their jobs. It feels like everyone gets laid off once they've been here long enough, and I know people here that haven't gotten a raise in 12+ years. It feels like they're determined to acquire as many competitors as possible, without pausing to consider the happiness of those that they currently employ. A ton of people are looking to leave or are unhappy. If you're going to work here, make it a stepping stone to something greater.