Pros
I worked with a great group of onsite and offshore developers. I could depend on everyone to complete their jobs. I had a good manager that supported the team and felt like he always considered our best interests. Although the technology stack for the company moved very slow, the team I worked for continually pushed the envelope trying new things and working toward staying relevant. I enjoyed my career at Esurance.
Cons
Slow moving technology stack. New CIO has a great vision, just unsure how the ship will change course. Moves made before I left were a step in the right direction, just hope tunnel vision and bias toward certain technologies don't turn it in the wrong direction. Too many managers. Work/Life balance although constantly talked about was lacking. See change management below for why. Not great health insurance. Was great when I started, but each year more and more was shouldered by the employee and less and less quality of care was offered.