Avoid this unsympathetic company
Avoid this unsympathetic company
A positive aspect of the company is its mental health benefits, which some employees use to make work better.
Although the company’s mission is noble, it is not the case for employees. The CEO appears focused on personal profit, thus demanding hard work from staff. Multiple co-founders have come and gone, and leadership is very unstable.
Despite raising Series D funding, they function as a Series A start-up. Even with great performance, the CEO can still fire you.
Because of bad engineering, the platform has flaws and will fail; however, the CEO is unconcerned. Politics shape the environment, making it hard to know allies.
If you truly want to solve for the mission, then put that above your personal interests.
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Headway Interview Experiences
Senior Software Engineer
I applied through a recruiter. The process took 1 week. 30 min call with recruiter followed by a 1 hour technical screen via Karat a third party interviewing service (so not a Headway employee). Next step would have been an onsite with 4 interviews:
Software Engineer
Quick and efficient interview process, very interesting company and mission. Would definitely enjoy working here, and the engineer who interviewed me seemed very competent and excited about the company. There is both a San Francisco and a New York of
Senior Software Engineer
Phone screen Virtual On-site (1 System Design, 1 Coding, 1 Behavioral) Meet with the teams The recruiting team was very responsive, transparent, and moved quickly. I had a great time meeting everyone on the team. All the questions asked were specif
Senior Software Engineer
San Francisco, California, United StatesJuly 24, 2026I applied through a recruiter. The process took 1 week. 30 min call with recruiter followed by a 1 hour technical screen via Karat a third party interviewing service (so not a Headway employee). Next step would have been an onsite with 4 interviews:
Software Engineer
San Francisco, California, United StatesOctober 2, 2024Quick and efficient interview process, very interesting company and mission. Would definitely enjoy working here, and the engineer who interviewed me seemed very competent and excited about the company. There is both a San Francisco and a New York of
Senior Software Engineer
United StatesMarch 25, 2025Phone screen Virtual On-site (1 System Design, 1 Coding, 1 Behavioral) Meet with the teams The recruiting team was very responsive, transparent, and moved quickly. I had a great time meeting everyone on the team. All the questions asked were specif
