Pros
Progressive is an environement where you are constantly placed in situations that are challenging and thought provoking. However, the amount of support you get in any of these situations is actually quite impressive. This truly is a place where everyone's opinion is valued and that your unique thoughts are incorporated into how the company does business. The career pathing particularly with indivudual managers is very good. As an employee you spend a very reasonable amount of time talking with management to determine where you will go next. It is the support and inclusiveness of the organization which make it a truly great place to work.
Cons
Progressive frequently suffers from a lack of visionary or strategic leadership. Most decisions are made very tactically which can lead to suboptimal results. Because the culture is so focused on analysis and quanititative skills, it can be hard for someone without those skills to be taken seriously or given opportunity. There is also a tendency to make quick judgements of data that, while statistically significant, does not feel right. This leads us to always stay down a consistent path, but not reward or recognize people who are willing to try something new and learn by failing. Additionally, the compensation for the amount of work that is required of you is severly lacking. Salaried employees frequently spend 7 days a week working and are paid rather low for what they contribute.