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      Senior Software Engineer Interview

      Jul 8, 2026
      Anonymous Interview Candidate
      No offer
      Negative experience
      Average interview

      Application

      I interviewed at HealthSherpa

      Interview

      This process is incredibly lengthy, spanning six rounds. Surprisingly, each round concluded on a positive note. Their apparent genuine concern for helping people appears to be a ruse, as I was ghosted. It’s disrespectful to people’s time.

      Other Senior Software Engineer Interview Reviews for HealthSherpa

      Senior Software Engineer Interview

      Jan 20, 2025
      Anonymous Interview Candidate
      No offer
      Positive experience
      Average interview

      Application

      I applied through a recruiter. The process took 8 weeks. I interviewed at HealthSherpa in Dec 2024

      Interview

      - Screening / informational with Recruiter - Behavioral interview with Recruiter - Behavioral / technical with VP of Engineering - Two code challenges (non-leet) - "Onsite" behavioral with CEO and Product/Eng management Overall I think the interview process was fine- I made it all the way through to the final stages until getting rejected. The second behavioral with the recruiter felt redundant? It was some standard "explain a project when.." type of questions which I'm sure was trying to get an idea of whether you are actually a good fit for the role before bringing in the Eng team, but in the context of how many other interviews I did, it seemed somewhat extraneous. The VP interview was another "explain a project you were a part of that was complex"-type of questions, with one technical question (simple, not coding, mine was about data modeling). The recruiter will prep you for this interview by saying something like "please be prepared, the VP appreciates clear, thoughtful communication" which made him sound really intense but after chatting I thought he was nice. You get the choice of doing the code challenges in one day, or doing them separately. The challenges were fine, the first one is in Javascript (I did React) and was relevant to something you might build as a product feature. The vibe of this interview was kind of weird though- the interviewers barely gave me an intro and were very quiet the entire time (one person even had their camera off). They also didn't allot enough time for me to ask questions at the end; I actually had to suggest we stop when there was 2 minutes left so I could ask them about their jobs and the company. They were quite personable during the Q+A so not a major red flag about working there, it just felt amateur-ish. You should go into these pretty confident to avoid the awkwardness. The Ruby exercise was to build a game (they tell you ahead of time), which was fun but I doubt very relevant to anything they do at HealthSherpa. I find it annoying that this is how they choose to test candidates, but again, it was at least fun and I did well on it. This interviewer seemed much more organized/experienced. The following "on-site" is a two-parter, you do one hour interview with their CEO and one hour interview with the hiring manager and the PM for the team. The latter also included a new Director of Engineering when I was interviewed. Both are fairly standard behavioral interviews. The CEO was quite conversational, he had a few pre-prepared questions but also asked for basically my life story and tried to get an idea of who I was as a person. He's also pretty personable- I probably liked him the most out of everyone I met at the company. The PM/EM interview was all pre-prepared questions. Again, no major red flags from the team, no crazy gotcha questions. I think the PM seemed competent and the EM was nice enough. I would have probably accepted an offer if they had given me one, but ultimately I was rejected after the on-site.

      Interview questions [1]

      Question 1

      Explain a time when you were working on a project with ambiguous requirements. How did you handle it? (paraphrasing)
      Answer question
      1

      Senior Software Engineer Interview

      Feb 8, 2025
      Anonymous Interview Candidate
      No offer
      Positive experience
      Average interview

      Application

      I applied through a recruiter. The process took 2 months. I interviewed at HealthSherpa in Dec 2024

      Interview

      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. 1. Recruiter Screen: I was contacted by a recruiter and we had an informational chat about my background and what the needs of the company are. 2. Formal Behavioral Interview: The same recruiter asked me a series of behavioral questions and took notes. They passed those notes on to the hiring manager. 3. Hiring Manager Interview: Had an hour-long interview with a VP that consisted of behavioral-based questions and some technical questions. There was no coding or whiteboarding. 4. BE Coding Interview: 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. 5. FE Coding Interview: This was 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. 6. Panel Interview: 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. 7. Founder Interview: 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.

      Interview questions [1]

      Question 1

      Walk me through the most complicated tech project you worked on (what was your role, why was it complicated). Tell me about a time you worked with a team to achieve a successful outcome.
      Answer question