Headway

Software Engineer Interview Experience

December 18, 2024

Negative ExperienceNo Offer

Process

The first round is easy LeetCode intervals, the second is project experience.

Onsite is the usual system design suspects.

Know REST, specifically FastAPI, for the coding round, even if the job you're interviewing for is completely unrelated.

At the end of the day, the interviews for this company are mostly about culture fit. There doesn't seem to be a serious engineering focus, so do your best to connect with them.

Questions

API rate limiter in FastAPI

Was this helpful?

Interview Statistics

The following metrics were computed from 17 interview experiences for the Headway Software Engineer role in United States.

Success Rate

18%

Pass Rate

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

Experience Rating

Positive41%

Neutral24%

Negative35%

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

Headway Work Experiences

Exciting mission, solid execution

Software Engineer • Current Employee

Palo Alto, California, United States

October 8, 2021

Pros: Explosive product market fit. Mental healthcare space is growing fast. Employees are very mission-focused. Work/life balance is strongly encouraged.

Cons: * Low compensation * There's an endless mountain of work to do, and company structure will change to support what is considered the top priorities.

Exciting mission, solid execution

Software Engineer • Current Employee

Palo Alto, California, United States

October 8, 2021

Pros: Explosive product market fit. Mental healthcare space is growing fast. Employees are very mission-focused. Work/life balance is strongly encouraged.

Cons: * Low compensation * There's an endless mountain of work to do, and company structure will change to support what is considered the top priorities.

Great group of people

Software Engineer • Current Employee

Pros: Everyone I’ve interacted with has been a top-tier person, incredibly talented, and fully engaged. Something that is not guaranteed at a larger company. The projects are incredibly impactful to the company’s trajectory. Work that makes it to an engineer’s plate is definitely the most important work they could be doing for the company.

Cons: It's really a choose-your-own-adventure. If you’re a self-starter or are not afraid to ask good questions, you’ll probably do well. If you don’t, you may not do as well.

Great group of people

Software Engineer • Current Employee

Pros: Everyone I’ve interacted with has been a top-tier person, incredibly talented, and fully engaged. Something that is not guaranteed at a larger company. The projects are incredibly impactful to the company’s trajectory. Work that makes it to an engineer’s plate is definitely the most important work they could be doing for the company.

Cons: It's really a choose-your-own-adventure. If you’re a self-starter or are not afraid to ask good questions, you’ll probably do well. If you don’t, you may not do as well.

Meaningful work with people who genuinely invested

Software Engineer • Current Employee

October 5, 2026

Pros: Headway is a genuinely fun place to work, and a lot of that comes from the people. Engineers are heavily invested in building a good product and are quick to help. The company has a strong mission, which makes work feel meaningful.

Cons: There are still some startup growing pains. Priorities can shift suddenly, which sometimes means changing direction mid-project. Depending on how you like to work, that's either exciting or frustrating. It keeps things moving, but it can be hard to plan around.

Meaningful work with people who genuinely invested

Software Engineer • Current Employee

October 5, 2026

Pros: Headway is a genuinely fun place to work, and a lot of that comes from the people. Engineers are heavily invested in building a good product and are quick to help. The company has a strong mission, which makes work feel meaningful.

Cons: There are still some startup growing pains. Priorities can shift suddenly, which sometimes means changing direction mid-project. Depending on how you like to work, that's either exciting or frustrating. It keeps things moving, but it can be hard to plan around.

Exciting mission, solid execution

Software Engineer • Current Employee

Palo Alto, California, United States

October 8, 2021

Pros: Explosive product market fit. Mental healthcare space is growing fast. Employees are very mission-focused. Work/life balance is strongly encouraged.

Cons: * Low compensation * There's an endless mountain of work to do, and company structure will change to support what is considered the top priorities.

5.0
Exciting mission, solid execution
Software Engineer • Current Employee
Palo Alto, California, United States
October 8, 2021
Pros: Explosive product market fit. Mental healthcare space is growing fast. Employees are very mission-focused. Work/life balance is strongly encouraged.
Cons: * Low compensation * There's an endless mountain of work to do, and company structure will change to support what is considered the top priorities.

Great group of people

Software Engineer • Current Employee

Pros: Everyone I’ve interacted with has been a top-tier person, incredibly talented, and fully engaged. Something that is not guaranteed at a larger company. The projects are incredibly impactful to the company’s trajectory. Work that makes it to an engineer’s plate is definitely the most important work they could be doing for the company.

Cons: It's really a choose-your-own-adventure. If you’re a self-starter or are not afraid to ask good questions, you’ll probably do well. If you don’t, you may not do as well.

5.0
Great group of people
Software Engineer • Current Employee
June 12, 2024
Pros: Everyone I’ve interacted with has been a top-tier person, incredibly talented, and fully engaged. Something that is not guaranteed at a larger company. The projects are incredibly impactful to the company’s trajectory. Work that makes it to an engineer’s plate is definitely the most important work they could be doing for the company.
Cons: It's really a choose-your-own-adventure. If you’re a self-starter or are not afraid to ask good questions, you’ll probably do well. If you don’t, you may not do as well.

Meaningful work with people who genuinely invested

Software Engineer • Current Employee

October 5, 2026

Pros: Headway is a genuinely fun place to work, and a lot of that comes from the people. Engineers are heavily invested in building a good product and are quick to help. The company has a strong mission, which makes work feel meaningful.

Cons: There are still some startup growing pains. Priorities can shift suddenly, which sometimes means changing direction mid-project. Depending on how you like to work, that's either exciting or frustrating. It keeps things moving, but it can be hard to plan around.

5.0
Meaningful work with people who genuinely invested
Software Engineer • Current Employee
New York, NY
October 5, 2026
Pros: Headway is a genuinely fun place to work, and a lot of that comes from the people. Engineers are heavily invested in building a good product and are quick to help. The company has a strong mission, which makes work feel meaningful.
Cons: There are still some startup growing pains. Priorities can shift suddenly, which sometimes means changing direction mid-project. Depending on how you like to work, that's either exciting or frustrating. It keeps things moving, but it can be hard to plan around.

Copyright © Taro