HealthSherpa Interview Questions
& Process

Stay away from HealthSherpa’s interview process, it was the worst and most disrespectful hiring experience. They made me go through months of endless interviews (recruiter, IT Manager, engineer, and even the founder, which I had to wait over a month for). After all that time and effort, they decided not to hire me with no feedback. Worse, they had wasted my time months earlier by engaging me as a contractor, then pulled the plug. A few months later, they brought me back for a full-time position, repeated the entire process, and rejected me again after three months. This company has no respect for candidates’ time. They change their hiring strategy midstream, are disorganized, and string people along with no consideration for the effort involved. It left me with a very poor impression of their culture and leadership. If you value your time and sanity, do not bother interviewing here. There are far better companies out there.

This was a thorough and intentional interview process that I actually appreciated and enjoyed. Everyone I met was nice and spoke well about the company and it's mission. The entire process was virtual. First, a recruiter reached out and we had an informational chat about my background and what the needs of the company are. Then, the same recruiter asked me a series of behavioral questions and took notes. Those notes were passed on to the hiring manager. Next, I had an hour-long interview with a VP that consisted of behavioral-based questions and some technical questions. There was no coding or whiteboarding. After that, I met with an engineer to solve a backend problem and they allowed me to write it in Python. It wasn't an algorithm, but more like writing a piece of code for a game. Then came a JS/React interview. I actually found the prompt to be slightly confusing. I wasn't sure exactly what they were looking for. But I must have done well-enough. Finally, I met with a Product Manager and an Engineering Manager at once. They asked questions about how I collaborate, projects I've worked on, and how I have worked with PMs and engineering teams in the past. I also had a very nice conversation with the founder/ceo. They had a set of behavioral and experience-related questions but it also felt like a vibe check. Ultimately I was rejected, but I think they gave me a fair shot.

I was contacted by the company for an Executive role that they needed to fill. Although I wasn't actively searching, the position looked interesting, and the employees seemed genuinely passionate about their work. The company would set up a call with me before each stage to get me ready. I suppose they really cared about their work and who they were presenting to the interviewing panel. I had a panel interview (Round 3!), and the employee who was so "involved" in maintaining open and transparent communication let me know a week later that they were moving forward with other candidates. I inquired about any feedback from the 3rd round, but received no response. If I was expected to provide feedback after each call, I would expect the same from the company too.

The interview process kicked off with a screening call from the recruiter. This was followed by a behavioral interview with the same recruiter, featuring lots of 'tell me about a time when...' type questions. Next up was a Technical System Design / Open-Ended question interview with the VP of Engineering. After that, I had a Coderpad Programming Challenge Interview where the task was to program a small game. Then came a Coderpad Software Design Challenge Interview focusing on expertise with a specific web framework; unfortunately, I didn't get past this stage. The process continued with Virtual on-site #1 and Virtual on-site #2. Finally, there was an interview with the CEO/CTO of the company. Overall, the people were nice, but the process felt way too long, took too much time, and was drawn out.