Process
I applied through an employee referral. The process took 2 weeks.
Felt very qualified for the role (perhaps even stronger technically than the Engineering Lead). During the interview, I felt like I shared key examples of my tech experience. Overall, I just felt disrespected by the interview team.
Questions
Tell me about a time you led a major technical decision without direct authority.
Tell me about the most complex system you’ve designed. What made it hard?
Was this helpful?
Interview Statistics
The following metrics were computed from 1 interview experience for the Headway Staff Engineer role.
Success Rate
0%
Pass Rate
Headway's interview process for their Staff Engineer roles is extremely selective, failing the vast majority of engineers.
Experience Rating
Positive0%
Neutral0%
Negative100%
Candidates reported having very negative feelings for Headway's Staff Engineer interview process.
Headway Work Experiences
5.0
Awesome people and meaningful work
Software Engineer • Current Employee
June 22, 2026
Pros: There are awesome people, meaningful work, a great work/life balance, lots of support, and executives who respond well to feedback.
Cons: Company-level goals can shift frequently.
5.0
Great mission, great people, a bit intense
Software Engineer • Current Employee
New York, New York, United States
November 25, 2025
Pros: Great mission, great people, strong performance, and roadmap.
Cons: A bit intense, but hey, we want to actually make an impact. When people care, things usually get a bit intense :)
5.0
Outstanding culture with incredible people
Director of Engineering • Current Employee
Los Angeles, California, United States
October 13, 2025
Pros: The culture at Headway is phenomenal — people are genuinely kind, motivated, and mission-driven.
The energy across the company is contagious, and you can feel how much everyone cares about what we’re building.
The growth trajectory is incredible, and it’s exciting to be part of a team scaling this fast.
The onboarding process was one of the best I’ve experienced in tech — thoughtful, well-organized, and designed to set you up for success from day one.
Cons: Not many so far. The pace is fast and the company is evolving quickly, so there’s some ambiguity at times—but that’s also part of what makes it exciting.
- 5.0Awesome people and meaningful workSoftware Engineer • Current EmployeeJune 22, 2026Pros: There are awesome people, meaningful work, a great work/life balance, lots of support, and executives who respond well to feedback.Cons: Company-level goals can shift frequently.
- 5.0Great mission, great people, a bit intenseSoftware Engineer • Current EmployeeNew York, New York, United StatesNovember 25, 2025Pros: Great mission, great people, strong performance, and roadmap.Cons: A bit intense, but hey, we want to actually make an impact. When people care, things usually get a bit intense :)
- 5.0Outstanding culture with incredible peopleDirector of Engineering • Current EmployeeLos Angeles, California, United StatesOctober 13, 2025Pros: The culture at Headway is phenomenal — people are genuinely kind, motivated, and mission-driven. The energy across the company is contagious, and you can feel how much everyone cares about what we’re building. The growth trajectory is incredible, and it’s exciting to be part of a team scaling this fast. The onboarding process was one of the best I’ve experienced in tech — thoughtful, well-organized, and designed to set you up for success from day one.Cons: Not many so far. The pace is fast and the company is evolving quickly, so there’s some ambiguity at times—but that’s also part of what makes it exciting.
Explore Interview QuestionsTaro 75Google Interview QuestionsMeta Interview QuestionsAmazon Interview QuestionsApple Interview QuestionsNetflix Interview Questions
Explore Interview ExperiencesOpenAI Interview ExperiencesAnthropic Interview ExperiencesPerplexity Interview ExperiencesWindsurf Interview ExperiencesMistral AI Interview Experiences
