Headway (NY) Customer Support Associate Interview Questions
& Process

My interview experience with Headway was nothing short of amazing. Every step of the process felt intentional, thoughtful, and incredibly human. The team made me feel supported, respected, and genuinely excited about the opportunity. From the first conversation to the final round, I was consistently impressed by the clarity, communication, and kindness shown throughout. It’s clear that Headway not only values talent but also the experience of each candidate—and that speaks volumes about the culture.

So, the hiring process outline was at the bottom of the email they sent me. It has 5 steps total, ending with the offer. The first interview is a quick 30 min meeting with someone from the talent team. After that, they told me the next step was different than usual. Normally it's a take home test, but they changed it to a live exercise this time. Then there's a prep meeting with the talent team again to talk about what they expect for the next two interviews, which are behavioral. If you pass those, they'll check your references, and then there's the offer meeting. It was a test of patience, especially how you handle yourself under different circumstances.

I'm super unhappy with Headway's hiring process. First off, there were way too many interviews, like 5, all at least 30 mins. Plus, I had to do a take-home assessment that took about an hour. The assessment itself was fine, but all the interviews after that felt like overkill since I already showed I could do the job. Also, a lot of the questions felt repetitive across interviews, asking about the same things like managing emotions, resilience, and communication over and over. What really got me, though, is how they handled things being neurodivergent. They knew I'm autistic and talked a big game about accommodations and changing their process, but it wasn't real. They'd give you 'accommodations' but still expect you to answer like a neurotypical person. It felt discriminatory. I proved I could do the job and gave examples, and they even admitted they were impressed, but then they assumed I wouldn't like the role. They presented the company culture and workload clearly, and I said I was fine with it, but they decided for me that I wouldn't like the job anyway. They also asked misleading questions, like asking about tough times but not wanting to hear anything negative or about how you were resilient without describing the hard time. Basically, Headway makes you do way too many interviews, assumes they know what you'll like better than you do, and their talk about accommodating neurodivergent candidates is just for show and actually biased towards neurotypical people. Their assumptions trump your actual abilities and what you say.