The entire process took about a month, mostly due to scheduling. I initially received an email from an in-house recruiter, which was followed up by a 30 minute phone interview. During that time, I was asked very simple and generic questions, probably to evaluate my personality. He was nice, engaging, and answered any questions I had. After that I received an email from him requesting that I come in to meet with three EAs (separately) for more interviews. Getting to this location is quite easy and the office space is very impressive, if you like open spaces with very little privacy or personal desk space (not a complaint). I ended up meeting with two EAs, who were really lovely (45 minutes each). They were both really nice and asked very typical questions for this position. I then got a tour of the entire space, which was quite encouraging. That evening I received an email from a different recruiter asking that I come in and interview with the three Executives I'd be supporting. I admit, that part was absolutely nerve wracking. The interview space was tiny and incredibly hot. Two of the interviews were pleasant. The third didn't go as well, part of it was probably my fault. Three interviews back-to-back by lawyer-types in a hot tiny box didn't help my chances. I sent a typical thank-you email to all parties and received two very pleasant responses. Unfortunately, that was the end of it. I would have liked to receive a "thanks but no thanks" email at some point, even a generic one. After all that time, I think that would have been the right thing to do on their part. Still, Castlight seems like a very good company to work for, even though I got the impression from other EAs that the workload is quite heavy. Two of the emails I received from the recruiters were sent at about 10 p.m.