Pros
The culture is second-to-none. Everyone had each other's backs and we truly work as "one team". I've worked here a year and have not had one single negative interaction with a coworker. It's a breath of fresh air compared to previous companies I've worked! The work is fast-paced and challenging (in a good way) and the work/life balance is very fair, at least in my department. They want you to take care of yourself and to ensure that you're not burning yourself out. They really focus on diversity and inclusion of everyone and people are very respectful of one another. Management is really engaged in the health and wellbeing of the individual, more than any other company I've ever worked for. I'm a remote employee and I feel they really support their remote workers.
Cons
There are silos and some departments seem compartmentalized in terms of their communications. This could be because we're so spread out across the country and Covid has certainly added to some of that complexity. However, if you're willing to reach out and break down barriers, I feel that everyone is completely open to helping one another in the most positive way, so from that standpoint it's less of a con and more of an opportunity. Getting budgetary approval can be challenging on some things although I'm sure Finance sees that as a pro. Castlight is a fiscally conservative company and so that's not a bad thing; it just can present some challenges in operations and planning.