Pros
It's difficult to discuss pros, because a lot had been changing with the company during the couple years before I left. Many positives were becoming negatives as I made the decision to leave. Laid-back work environment. No one breathes down your neck. Breaks, lunch, etc. are very relaxed. The atmosphere promotes relaxed people, so you'll enjoy your coworkers and you'll make friends there. You can probably work at home. Pay and benefits are solid for the work you do. Paid training - they pay you to get your insurance license.
Cons
No more flexible scheduling, which Progressive used to be famous for. They now use performance-based scheduling, the outrageous unfairness of which is hard to comprehend. Although Progressive puts way less emphasis on numbers that certain other companies do, they still put too much emphasis on numbers, and not enough emphasis on the way you actually do your job and the ultimate bottom-line results of what you do. The company is way too modular, with different departments unwittingly working against each other.