Castlight Customer Success Manager Interview Questions
& Process

I applied online and HR got back to me about two months later. The interview process was quite long. First, there was a recruiter phone screen. Then, they wanted to move forward, so I had five separate 1-hour phone interviews with different people on the team in various roles over about a month and a half. After that, I had a 30-minute video call with the VP of the team. I felt like I answered all their questions well, but I don't think the time was sufficient, especially considering I have over 15 years of experience and was more than qualified. I received positive feedback from everyone else I interviewed with. So, after more than 6 interviews, totaling over 8 hours across nearly two months, I was not offered the role. They said I was talented and had the necessary qualifications but weren't sure I was a good fit for the team, though I might be for another. It was a waste of my time, as qualifications and fit are different things, and they likely knew about the fit issue much earlier.

The interview process was long, intermediate in difficulty, and somewhat disorganized. It started with a phone screening with a talent acquisition rep who didn't know much about the role or company. After that, there were two more phone interviews with director-level employees, which were better organized. The next step was a 3-hour in-person interview with an Associate Customer Success Manager, a Customer Success Manager, and one of the directors. During this interview, a "case study" was included, which was actually just a quick test of reading an Excel sheet. Everyone met was great and spoke positively about leadership. Big takeaways: people were great, the services team seems to be heading in a good direction, but I was skeptical about the company's long-term viability because they recently lost a major client, though nobody seemed to want to discuss it. The office seemed a bit quiet and bleak, but I only saw it for 30 minutes. I didn't get the offer. The recruiter let me know promptly, which was appreciated. However, after investing many hours in interviews, I would have expected the hiring manager or a director to reach out with more feedback, especially for a smaller company.

This was the best interview and recruiting process I've experienced. Robert was a great partner throughout, providing helpfulness, transparency, responsiveness, and honesty about expectations, the process, and the timeline. He was supportive at every stage, and I'm grateful for his partnership in helping me achieve my career goals.