Headway

Senior Software Engineer Interview Experience

June 18, 2024

Neutral ExperienceGot Offer

Process

Long interview process, but for the most part fair. They let you know in advance everything to prepare for. I recommend brushing up on some DS/algo, as well as some system design prep.

First round is a simple LeetCode easy: finding a time slot given existing time slots. Second round is going over a project. Finally, onsite, which is one more technical (LC easy/medium), systems design (they ask you to design a system similar to a product they may roll out), and behavioral questions.

Questions

Given an array of dates and times of schedules, find the narrowest available time slot.

Go over a project that you had the broadest scope of ownership over.

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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

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.

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.

Inspiring team culture with complex healthcare challenges

Engineering Manger • Current Employee

San Francisco, CA

Pros: The people are easily the best part: talented, low-ego, and genuinely invested in each other's success. We're helping people get access to mental healthcare, and that shows up in the work in a real way that inspires what we do every day. Headway is also fully leaning into leveraging AI in our daily workflow, which makes it an incredibly exciting place to build.

Cons: Healthcare is heavily regulated, so you can't always ship the obvious thing because there are real constraints, and navigation can feel slow if you're coming from a consumer pace. The user base is also wildly broad, including patients, providers, group practices, payers, and internal ops. That means getting the long tail right is pretty hard, and what works for one segment often misses another.

Inspiring team culture with complex healthcare challenges

Engineering Manger • Current Employee

San Francisco, CA

Pros: The people are easily the best part: talented, low-ego, and genuinely invested in each other's success. We're helping people get access to mental healthcare, and that shows up in the work in a real way that inspires what we do every day. Headway is also fully leaning into leveraging AI in our daily workflow, which makes it an incredibly exciting place to build.

Cons: Healthcare is heavily regulated, so you can't always ship the obvious thing because there are real constraints, and navigation can feel slow if you're coming from a consumer pace. The user base is also wildly broad, including patients, providers, group practices, payers, and internal ops. That means getting the long tail right is pretty hard, and what works for one segment often misses another.

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.

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.

Inspiring team culture with complex healthcare challenges

Engineering Manger • Current Employee

San Francisco, CA

Pros: The people are easily the best part: talented, low-ego, and genuinely invested in each other's success. We're helping people get access to mental healthcare, and that shows up in the work in a real way that inspires what we do every day. Headway is also fully leaning into leveraging AI in our daily workflow, which makes it an incredibly exciting place to build.

Cons: Healthcare is heavily regulated, so you can't always ship the obvious thing because there are real constraints, and navigation can feel slow if you're coming from a consumer pace. The user base is also wildly broad, including patients, providers, group practices, payers, and internal ops. That means getting the long tail right is pretty hard, and what works for one segment often misses another.

5.0
Inspiring team culture with complex healthcare challenges
Engineering Manger • Current Employee
San Francisco, CA
May 26, 2026
Pros: The people are easily the best part: talented, low-ego, and genuinely invested in each other's success. We're helping people get access to mental healthcare, and that shows up in the work in a real way that inspires what we do every day. Headway is also fully leaning into leveraging AI in our daily workflow, which makes it an incredibly exciting place to build.
Cons: Healthcare is heavily regulated, so you can't always ship the obvious thing because there are real constraints, and navigation can feel slow if you're coming from a consumer pace. The user base is also wildly broad, including patients, providers, group practices, payers, and internal ops. That means getting the long tail right is pretty hard, and what works for one segment often misses another.

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