Glassdoor users rated their interview experience at Headway as 100% positive with a difficulty rating score of 2 out of 5 (where 5 is the highest level of difficulty). Candidates interviewing for Programme Analyst and rated their interviews as the hardest, whereas interviews for Programme Analyst and roles were rated as the easiest.
Here are the most commonly searched roles for interview reports -
I applied through a recruiter. I interviewed at Headway (San Francisco, CA) in Nov 2025
Interview
I was reached out by a recruiter. The recruiter has to discuss your profile with a hiring manager to move you forward.
I found the recruiter to be incredibly kind and very easy to speak with. I also knew I met the qualifications for the role and exceeded it in some areas.
I found this one line from the rejection email to be extremely elitist and off-putting:
"As a startup, sometimes our hiring can be selective as we get off the ground and that rings especially true on Product where the team can be incredibly selective as we seek out a mix of domain knowledge and product experiences on teams and at *companies* that feel well aligned with us."
I looked on LinkedIn and almost all PMs they hire from are from FAANG companies. I did the interview because a recruiter reached out to me. I did not apply for a role at this company. You can see the company I work at from my resume. You do not have to interview people from companies that are not aligned with your company to begin with.
I felt like this response was one of the worst responses I have gotten from a company. Talent can be in any type of company or team (despite the size, scale, or the reputation). You cannot judge someone on that. Rather, you can assess them on their career trajectory, their skillset, and what they have built.
If this rejection was due to lack of match in skills or, shortcomings I showed in the interview (i.e. lack of experience in XYZ space), it would not bother me at all. I have had plenty of rejections and I see the hiring manager's perspective most times but, this felt weird.
I do need therapy for writing this on a Friday night at 11:00PM. Thanks, Headway!
Interview questions [1]
Question 1
Standard behavioral questions
- tell me about your past experience
- product you're the most proud of
- experience working with technical teams (ML, eng, etc)
I applied through a recruiter. I interviewed at Headway
Interview
Met with the recruiter on the phone through a referral. Did not move to next phase (hiring manager interview). Was told it was difficult to make it past the recruiter.
I applied online. The process took 3 weeks. I interviewed at Headway (New York, NY) in May 2024
Interview
Interview was a really great process. Every step of the way had so much communication, and I always knew exactly what was next, how to prepare, and what to expect.
Interview questions [1]
Question 1
They have a very big mission so interview is a mix of skill related questions, and also behavioral type questions to make sure its a culture fit.