Pros
The people are great and pay is terrific. As for the day to day of working at castlight, you never know what you're going to get. The work is rewarding and thrilling to those eager to learn in the tech space. The company has strong leadership throughout the organization. Maeve our CEO has revitalized the Customer Success team while placing strong resourcing into the professional services team, making strong hires at the director levels will pay dividends for Castlight's future. There are dozens of incredibly talented individuals at the company and everyone is very willing to collaborate and learn from one another. Castlight has a terrific culture and despite recent unfortunate lay offs the attitude has mainly been positive and inspiring.
Cons
If you prefer to work strictly 40 hours a week and are not willing to put in extra time then I would consider this aspect of working here. It is a startup and constantly evolving and adapting so you must work extra hard to perform well. This can be great for those wanting a challenge but can overwhelm those are might not enjoy the requirement to be flexible. Working at Castlight around the month of December is also very busy if this time is important to you. Prepare to babysit other departments if you want things done right and quickly. Churn throughout the organization has hurt some of the internal processes.