Pros
Though only a few months into my time at Castlight, I have been greatly impressed by the overall cultural maturity of the organization. They treat you like a real, live grown-up, trusting that employees will do the right thing and are committed to getting the job done right. Additionally, the depth of really smart people solving a nation-wide problem is inspiring, and I'm getting used to being the dumbest guy in the room which is awesome for learning the healthcare transparency movement. Management does a great job of keeping staff up to date on company issues and developments, with the CEO giving a weekly all-hands meeting.
Cons
Still trying to find what that would be...maybe too much positive feedback and team support...it's unsettling when you are used to being abused at other companies.