1. Screening call with recruiter 2. Behavioral Interview with same recruiter with many "tell me about a time when..." type questions 3. Technical System Design / Open-Ended question interview with VP of Engineering 4. Coderpad Programming Challenge Interview where I needed to program a small game 5. Coderpad Software Design Challenge Interview where I needed to show expertise with a specific web framework. I did not make it past this stage 6. Virtual on-site #1 7. Virtual on-site #2 8. Interview with CEO/CTO of the company Overall, while everyone I spoke to was pleasant, the process seemed overly long, time-consuming, and drawn out.

I strongly advise candidates to stay away from HealthSherpa’s interview process. I’ve been a Software Engineer for 20+ years, and this was hands-down the worst and most disrespectful hiring experience I’ve ever had. They dragged me through months of endless interviews (recruiter, IT Manager, engineer, and even the founder, who I had to wait over a month for). After investing all that time and effort, they decided not to hire me — with no meaningful feedback. Worse, they had already wasted my time months earlier by engaging me as a contractor through a recruiting firm, then pulled the plug and said they weren’t hiring contractors anymore. 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 clearly 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 that treat candidates professionally and make timely, thoughtful hiring decisions.