Overall, the interviewer was friendly and succinct. It was a mix of behavioral questions and analytical questions. The interviewer also saved time at the end for me to ask questions.
Other Strategy and Operations Associate Interview Reviews for Headway (NY)
I interviewed at Headway (NY) (New York, NY) in Jan 2026
Interview
I only made it to the first hiring manager round. really scripted questions, didn't seem to interested in my answers and acted annoyed to be speaking with me. overall did not leave a positive impression of the team and I was not too disappointed to not get a call back.
I applied online. I interviewed at Headway (NY) in Jul 2025
Interview
It’s a 5-step process that takes around 3 weeks. Average to semi-difficult process. The first interview is a recruiter call and if you pass that you complete a ~5 hour take home project (claims data set where you give your findings and process improvement recs to “leadership” based on the data). Once that is reviewed and/if you pass, second interview is with the hiring manager for an overview of experience that relates to the role. They only ask two in-depth questions that you should plan to elaborate on intensely with several follow-up Qs. Take home assignment is never discussed. Third interview is a team lead or someone you directly report to for a live problem solving interview (non-related to healthcare, mine was on legalization of marijuana and how you would go about finding data to assist a governor with passing a federal law). It’s very similar to a consulting interview. Most of their operations staff and management appeared to have consultant background instead of health tech, so they’ve definitely structured the process based on that. However you will have a leg up if you have health-tech experience. The last interview is the cultural fit (peer or leadership), and they ask you to pick two values of theirs and discuss how you are great at one and working to improve on the other. Plan to discuss for 10 minutes each.
Long drawn out process in which if you don’t get the offer, they cannot provide you any feedback as to why you weren’t chosen for liability purposes. I found that to be unfortunate and a lack of transparency that does not support the mission. Competitor health-tech companies have been much more transparent in my experience.
Very kind people, but the fake positive atmosphere from the interviewers made the culture feel disingenuous and made it very hard to get a transparent view of the company’s real challenges and culture. Good luck if you get an interview!
Let’s say a governor is trying to legalize marijuana and they need your assistance in gathering data to support this law, what steps would you take to find the data? Where would you get this information and how would you ensure it’s accurate? Self-reported surveys and government reported agencies and records are excluded (like CDC). However you have all the resources at your hands that this governor can provide. Pitch a 1-2 minute summary of your findings to the governor once you completed your thought process.
Which one of our values is your biggest strength and why? Which one is your weakest and how are you improving it, and how can we as a company help you to continue to improve it?