Pros
1. A CEO who is not only visible and accessible, but who is intimately involved in the day to day of his employees' lives. He personally sends company-wide congratulatory e-mails re promotions, baby births, weddings, etc. And attends many of these personal events.
2. A worthwhile mission. Since transparency in healthcare has been nonexistent at best, Castlight is truly trying to revolutionize the way we look at healthcare and how we act as consumers of it. I can tell you from personal experience that everyone at the company has bought into the mission.
3. Collegial colleagues. Maybe this doesn't mean as much coming from someone who previously worked as an associate at a large Am Law 20/Chambers 10 law firm and as in-house counsel at a publicly traded company, but I haven't met this caliber of colleagues at any of those previous stops. Not only are folks incredibly smart - many graduated from top flight college and MBA programs, and others have M.Ph or MD degrees - but are humble about it and are genuinely very nice, happy, sympathetic, etc. I have not met a single difficult personality in my first 4 months. And it starts at the top with our leadership.
4. Flexibility. It's rare to work in an infrastructure group like Legal and be allowed to work remotely. The company is based in SF but I work from home in LA and fly up every 2-3 weeks for a few days to work from the office. In fact, the CEO encourages everyone to work from home at least a day a week to be closer to family. Pretty incredible.
Cons
I haven't been there long enough to see any downsides, to be honest, and am likely less exposed to them bc i work remotely, so can't be of much help on this one.
