Product Manager applicants have rated the interview process at Headway (NY) with 3 out of 5 (where 5 is the highest level of difficulty) and assessed their interview experience as 50% positive. To compare, the company-average is 43.9% positive. This is according to Glassdoor user ratings.
Common stages of the interview process at Headway (NY) as a Product Manager according to 4 Glassdoor interviews include:
Group panel interview: 17%
Skills test: 17%
One on one interview: 17%
Phone interview: 17%
Presentation: 8%
Personality test: 8%
Background check: 8%
Other: 8%
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Multiple rounds but fair. Also a presentation. Unclear standards and scope which resulted in an offer being rescinded after the fact despite checking all the interviews and references. Save your time interviewing with them unless they give you clear view in the role you’re actually being hired for
I applied through a recruiter. I interviewed at Headway (NY) (New York, NY) in Nov 2025
Interview
By far most organized of the companies I interviewed with this cycle. Every step had clear expectations and the later ones had collateral sent ahead to help prep. Feedback was always very prompt.
My process (for staff level) was:
- Recruiter screen
- Hiring manager screen
- first half panel: behavioral + collaborating on a partially finished draft PRD (they send ahead and I recommend marking up ahead but you could get away talking through live)
- second half panel: technical + presenting on work you’ve done
After that they’re basically in sell mode for you, which was different than other companies where late stage convos were sometimes ambiguous over whether you were still being evaluated.
Got to meet 2 people in person based on being in NYC but no obligation to do so
Interview questions [1]
Question 1
A LOT of talking through past work. Be prepared to talk about past disagreements, what you wish you did differently, what your role was vs others, what you were right vs wrong about, etc. Normal stuff, but in many different formats and through different stakeholder lenses.
The only thing that was more Headway specific was the PRD jam, where they sent you a draft PRD with obvious problems and gaps and asked me to help make it better
Role description didn’t seem to really align with what they were looking for. Seemed like they wanted someone much more analytical and data science oriented that had specific experience in calculated insights
Interview questions [1]
Question 1
Tell me about about your experience working with ML / AI teams