Headway

Senior Software Engineer Interview Experience

April 3, 2023

Positive ExperienceNo Offer

Process

The people I interviewed with were all really nice, and I think that's what made the process better. The 2-hour API design interview was kind of dumb, as I felt it was a drag for both the interviewer and interviewee. Whoever came up with this process doesn't understand what a candidate experience should be.

Questions

2-hour API design/implementation + 1-hour behavioral + 1-hour system design

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Interview Statistics

The following metrics were computed from 16 interview experiences for the Headway Senior Software Engineer role in United States.

Success Rate

25%

Pass Rate

Headway's interview process for their Senior Software Engineer roles in the United States is very selective, failing most engineers who go through it.

Experience Rating

Positive56%

Neutral13%

Negative31%

Candidates reported having very good feelings for Headway's Senior Software Engineer interview process in United States.

Headway Work Experiences

Unicorn Startup with a Top Tier Exec Team

Senior Software Engineer • Current Employee

Pros: - A bright engineering team. - An empathetic culture and good compensation and benefits. - First-time founder energy surrounded by industry veterans. - Varied work surfaces give a ton of different work experiences depending on the team.

Cons: No startup is perfect, and this is no exception. We struggle with planning and prioritization, and the communications from leadership aren't perfect, but overall, the people and the work make up for the pitfalls.

Unicorn Startup with a Top Tier Exec Team

Senior Software Engineer • Current Employee

Pros: - A bright engineering team. - An empathetic culture and good compensation and benefits. - First-time founder energy surrounded by industry veterans. - Varied work surfaces give a ton of different work experiences depending on the team.

Cons: No startup is perfect, and this is no exception. We struggle with planning and prioritization, and the communications from leadership aren't perfect, but overall, the people and the work make up for the pitfalls.

Hyper-growth with a heart

Senior Software Engineer • Current Employee

Pros: I’ve been with Headway since December 2020, and it is undoubtedly the best company I have ever worked for. Over the years, I’ve had the opportunity to work on deeply fulfilling projects while watching the organization expand significantly. The most rewarding aspect is knowing our work directly helps millions of people. Internally, the company treats its team exceptionally well. I have consistently felt that my work is respected and, more importantly, that I am valued as an individual rather than just a metric of output.

Cons: Because we are scaling so quickly, company priorities can shift rapidly. This means project roadmaps occasionally change abruptly, which can be frustrating when it leads to sudden pivots or having to walk away from work you've heavily invested in.

Hyper-growth with a heart

Senior Software Engineer • Current Employee

Pros: I’ve been with Headway since December 2020, and it is undoubtedly the best company I have ever worked for. Over the years, I’ve had the opportunity to work on deeply fulfilling projects while watching the organization expand significantly. The most rewarding aspect is knowing our work directly helps millions of people. Internally, the company treats its team exceptionally well. I have consistently felt that my work is respected and, more importantly, that I am valued as an individual rather than just a metric of output.

Cons: Because we are scaling so quickly, company priorities can shift rapidly. This means project roadmaps occasionally change abruptly, which can be frustrating when it leads to sudden pivots or having to walk away from work you've heavily invested in.

Mission-driven culture with growth opportunities, but fast pace

Engineering Manager • Current Employee

Pros: - Truly a mission-oriented company that does things the right way and wants to help patients and providers. - Some of the kindest and most intelligent coworkers you can imagine. - Tons of opportunity to grow your career and experience due to rapid scaling creating new opportunities every day. It's honestly a joy to be an EM here because the team is so strong due to a consistently high talent bar and huge focus during hiring on cultural alignment.

Cons: Aiming to be peers with really prestigious tech companies and AI labs, but the pay is still more B-tier tech (please add a 401(k) match!). Rapid growth means processes break before they can get fixed or replaced. The pace can get crazy, and a high-ownership culture can make work-life balance hard as you try to juggle the opportunities made available to you.

Mission-driven culture with growth opportunities, but fast pace

Engineering Manager • Current Employee

Pros: - Truly a mission-oriented company that does things the right way and wants to help patients and providers. - Some of the kindest and most intelligent coworkers you can imagine. - Tons of opportunity to grow your career and experience due to rapid scaling creating new opportunities every day. It's honestly a joy to be an EM here because the team is so strong due to a consistently high talent bar and huge focus during hiring on cultural alignment.

Cons: Aiming to be peers with really prestigious tech companies and AI labs, but the pay is still more B-tier tech (please add a 401(k) match!). Rapid growth means processes break before they can get fixed or replaced. The pace can get crazy, and a high-ownership culture can make work-life balance hard as you try to juggle the opportunities made available to you.

Unicorn Startup with a Top Tier Exec Team

Senior Software Engineer • Current Employee

Pros: - A bright engineering team. - An empathetic culture and good compensation and benefits. - First-time founder energy surrounded by industry veterans. - Varied work surfaces give a ton of different work experiences depending on the team.

Cons: No startup is perfect, and this is no exception. We struggle with planning and prioritization, and the communications from leadership aren't perfect, but overall, the people and the work make up for the pitfalls.

5.0
Unicorn Startup with a Top Tier Exec Team
Senior Software Engineer • Current Employee
New York, NY
June 23, 2026
Pros: - A bright engineering team. - An empathetic culture and good compensation and benefits. - First-time founder energy surrounded by industry veterans. - Varied work surfaces give a ton of different work experiences depending on the team.
Cons: No startup is perfect, and this is no exception. We struggle with planning and prioritization, and the communications from leadership aren't perfect, but overall, the people and the work make up for the pitfalls.

Hyper-growth with a heart

Senior Software Engineer • Current Employee

Pros: I’ve been with Headway since December 2020, and it is undoubtedly the best company I have ever worked for. Over the years, I’ve had the opportunity to work on deeply fulfilling projects while watching the organization expand significantly. The most rewarding aspect is knowing our work directly helps millions of people. Internally, the company treats its team exceptionally well. I have consistently felt that my work is respected and, more importantly, that I am valued as an individual rather than just a metric of output.

Cons: Because we are scaling so quickly, company priorities can shift rapidly. This means project roadmaps occasionally change abruptly, which can be frustrating when it leads to sudden pivots or having to walk away from work you've heavily invested in.

5.0
Hyper-growth with a heart
Senior Software Engineer • Current Employee
New York, NY
May 1, 2026
Pros: I’ve been with Headway since December 2020, and it is undoubtedly the best company I have ever worked for. Over the years, I’ve had the opportunity to work on deeply fulfilling projects while watching the organization expand significantly. The most rewarding aspect is knowing our work directly helps millions of people. Internally, the company treats its team exceptionally well. I have consistently felt that my work is respected and, more importantly, that I am valued as an individual rather than just a metric of output.
Cons: Because we are scaling so quickly, company priorities can shift rapidly. This means project roadmaps occasionally change abruptly, which can be frustrating when it leads to sudden pivots or having to walk away from work you've heavily invested in.

Mission-driven culture with growth opportunities, but fast pace

Engineering Manager • Current Employee

Pros: - Truly a mission-oriented company that does things the right way and wants to help patients and providers. - Some of the kindest and most intelligent coworkers you can imagine. - Tons of opportunity to grow your career and experience due to rapid scaling creating new opportunities every day. It's honestly a joy to be an EM here because the team is so strong due to a consistently high talent bar and huge focus during hiring on cultural alignment.

Cons: Aiming to be peers with really prestigious tech companies and AI labs, but the pay is still more B-tier tech (please add a 401(k) match!). Rapid growth means processes break before they can get fixed or replaced. The pace can get crazy, and a high-ownership culture can make work-life balance hard as you try to juggle the opportunities made available to you.

5.0
Mission-driven culture with growth opportunities, but fast pace
Engineering Manager • Current Employee
New York, NY
April 16, 2026
Pros: - Truly a mission-oriented company that does things the right way and wants to help patients and providers. - Some of the kindest and most intelligent coworkers you can imagine. - Tons of opportunity to grow your career and experience due to rapid scaling creating new opportunities every day. It's honestly a joy to be an EM here because the team is so strong due to a consistently high talent bar and huge focus during hiring on cultural alignment.
Cons: Aiming to be peers with really prestigious tech companies and AI labs, but the pay is still more B-tier tech (please add a 401(k) match!). Rapid growth means processes break before they can get fixed or replaced. The pace can get crazy, and a high-ownership culture can make work-life balance hard as you try to juggle the opportunities made available to you.

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