Customer Care Associate applicants have rated the interview process at Headway (NY) with 3.3 out of 5 (where 5 is the highest level of difficulty) and assessed their interview experience as 33% positive. To compare, the company-average is 43.9% positive. This is according to Glassdoor user ratings.
Candidates applying for Customer Care Associate roles take an average of 16 days to get hired, when considering 3 user submitted interviews for this role. To compare, the hiring process at Headway (NY) overall takes an average of 22 days.
Common stages of the interview process at Headway (NY) as a Customer Care Associate according to 3 Glassdoor interviews include:
Skills test: 40%
Phone interview: 40%
One on one interview: 20%
Here are the most commonly searched roles for interview reports -
I applied online. The process took 2 weeks. I interviewed at Headway (NY)
Interview
I had a fantastic experience interviewing for the Customer Care Associate position. From the very beginning, the recruiter, Sarah Cooper was professional, friendly, and communicative. I received clear details about the process and what to expect at each stage.
They also provided a deck of potential interview questions and details about the company's mission in advance, which allowed me to prepare thoughtfully and present my best self during the interview."
The overall interview process took about 2 weeks that were promptly scheduled. I appreciated that they took the time to give me feedback and answered all my questions about the company culture and team dynamics.
What stood out the most was the transparent communication throughout the process. I was always kept informed about next steps, and the feedback after each interview was constructive and timely.
Interview questions [1]
Question 1
Major changes/ transitions/ challenges that took place at work
I applied online. The process took 1 week. I interviewed at Headway (NY) (New York, NY) in Oct 2025
Interview
After I passed the initial screening I was interviewed in the live exercise where we worked on a simulated ticket and the interviewer was fantastic. She was delightful and told me I was her "favorite" person out of all the interviews.
When I advanced to the next stage as soon as I saw the behavioral person interviewing me the vibe was off immediately. She seemed uninterested, with long pauses, rushes me through as we finished in 20 minutes for what should have been a 45 minute scheduled interview.
I do appreciate receiving an email the same day but quickly looking on Linkedin, Headway seems to mostly have only women working there. There is no way a 50 year old male is going to be hired by them, period.
I spent all week researching Headway, learning their mission and delivered what was an amazing first interview.
In all, I don't think I looked like what they wanted, and I knew it immediately when the second interviewer saw my face.
Very disappointed.
Interview questions [1]
Question 1
What was the one thing you did outside your job description?
I applied through other source. The process took 4 weeks. I interviewed at Headway (NY) (Austin, TX) in Oct 2025
Interview
The interview process was a mixed bag. There was a total of three meetings. The first one was over the phone for a brief phone call with a recruiter who sounded very positive and encouraging. This then led to scheduling two additional follow-up Zoom video meetings. The first meeting was a live test of your skills. It included writing an email for a customer support scenario and a test of how you prioritize tasks in order of importance. The person who managed that part of the interview was pleasant and professional. The third and last meeting was a behavioral assessment with the typical questions that get asked in job interviews. The person who handled that interview was unprofessional, unkempt, and unfocused. She also mentioned a disrespectful and condescending way of referring to the current customer associate staff. Hearing that made me very suspicious of how the team might be treated, and it did not provide a good first impression to me. It did not make me feel she valued the employees in that role at all. I am extremely disappointed in how much this company WASTED MY TIME. If you care about being treated with respect in a customer service role, this might not be the right place for you.
Interview questions [1]
Question 1
Tell me about a time that you escalated a ticket to a manager. Tell me about how you handle a significant change in your company? What did you learn from that experience? Tell me about a time when you handled a difficult situation? Etc., Etc., Etc.