Pros
Castlight is clearly trying to define themselves in terms of culture. With no PTO policy (trust system), a Culture committee that is committed to continuing a great culture at Castlight, continuing weekly contact with the CEO with a Q&A, Events committee, Wellness committee, Volunteer committee - Castlight is a place where you can be as integrated with your work community as you would like. The support and kindness that I have witnessed at Castlight makes me wonder if I would ever get a work environment like it ever again.
Cons
Due to the nature of how fast the business is growing and how much we are trying to achieve in such a short period of time, anyone coming to Castlight had better be able to wear multiple hats. It is a company that is transitioning from very small to fully mature with true corporate structures, so if you like the small startup this place probably is not for you. If you like the community atmosphere with lots going on and having to be creative to find a way, then you might like it here.