I applied through a recruiter. I interviewed at Headway (NY) (New York, NY) in May 2026
Interview
I recently went through the interview process here and came away genuinely impressed. From the first conversation to the final round, the experience felt thoughtful and well-organized.
What stood out most was how informative the interviewers were. Rather than keeping things vague or one-sided, they took real time to share context about the role, the team, and what success actually looks like day to day. I left every conversation feeling like I understood the company better.
The questions were substantive and gave me a real chance to showcase my background, while the interviewers were engaged and made the conversations feel like genuine two-way exchanges rather than interrogations.
Overall, it's one of the best interviewing experiences I've had!
After one phone interview, they gave a written exercise case study that was extremely confusing and not clearly explained. They rejected mine with an automated email and no feedback. After the rejection, I ran my response by several friends in sales and a few AI platforms, and all thought it should have passed easily.
Interview questions [1]
Question 1
In the case study they asked about objection handling, how you would respond over email
I applied through a recruiter. The process took 2 weeks. I interviewed at Headway (NY) (Bellevue, WA) in May 2025
Interview
Terrible interview process. They make you take an at home test, then follow it up with 4 interviews. On my 2nd interview that involved behavioral questions, I don’t think the interviewer look at me once. I understand taking notes but for the love of god it was absurd. For such a low paying simple job, you’d guess they wouldn’t lead you on through all the interviews. This happened to me and another rep I have worked with. Don’t waste your time, this isn’t Amazon or Microsoft by any means. They underpay you and waste your time.
We’re sorry to hear that your interview experience didn’t meet expectations. We strive to provide an interview process that is transparent, engaging, and fair. If you’re open to sharing more directly so that we can improve, feel free to connect with us at reach-out@findheadway.com.