Pros
In my experience, the best reasons for working at Progressive iinclude an environment that fosters good work/life balance and opportunities to expand one's career. I believe that one has the flexibility to change careers better than most companies that I have worked. It is entirely on the individual to determine where they want to go.
Cons
When it comes to senior leadership positions, a downside can be the empasis that gets placed on the prestige of certain MBAs vs. the actual substance of the individual. While this is probably common across the industry, I think capable leaders who generate results are at a disadvantage because their MBA isn't from a top 10 instituition. Not everyone's circumstances in life can afford them that opportunity. For example, I admire high performers who have committed themselves to earning their Masters in the evenings because they have to provide for a family.