Pros
Well funded. Some employees (mainly the original few) believe they can change the face of healthcare, and the energy and belief of what Castlight's mission was for some was unparalleled. Great monetary compensation and the Company honestly tried to foster a belief of transparency and unity.
Cons
They have a lot of smart people working there: MDs, phDs, etc. But these people have never worked a) period or b) if they have, worked in a web/software environment. They don't relate to the audience or understand how to build software from scratch. They do user research, but don't pay attention - the tool is completely unusable and they won't change it because...? They just won't. The Company, in the interest of doing business, seemed to have lost its way and started functioning as an HMO for their larger clients, rather than providing the service the promised to their users. This changed the dynamic within and perception of the Company. That said, employees who didn't see eye-to-eye with this viewpoint either left or were laid off.