Engineering Manager at Headway | Powderkeg

Headway’s mission is a big one - to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to take insurance and scale their practice.

Headway was founded in 2019 – since then, we’ve grown into a diverse, national network of over 25,000 mental healthcare providers across all 50 states who run their practice on our software. We’re a Series C company with over $225m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

Principles that guide us:

  • Focus on the mission : We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapists to better solve the problems they’re facing.
  • Ship small, learn fast : We are building new and novel products and believe that we learn what our users need by quickly shipping and iterating
  • Everything is a product : Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
  • Optimize for trust : We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

  • Languages : Python 3, TypeScript
  • Libraries : FastAPI, SQLAlchemy, React
  • Datastores : Postgres, Redis, DynamoDB
  • Infrastructure : AWS (Fargate, ECS, S3, and more), Spark, Flink, and Kafka
  • Monitoring : Datadog, PagerDuty
  • Version control : Github

Team leadership opportunities:

There is a lot that we're building at Headway, but here are a few teams we’re building where your engineering leadership could make a measurable impact:

  • Clinical Compliance : This new team is building systems to determine the compliance of clinical documentation at scale. We want to make it as easy as possible for our providers to maintain compliant clinical records so they can focus on what they do best – helping clients. This team is building a Machine Learning powered platform to ensure that providers can understand the compliance of their documentation and we can understand the compliance of our entire network of providers. Building products and platforms to support clinical compliance for Headway providers.
  • Payments : This new team is building the groundwork for a scalable financial system at Headway, including a robust Revenue Cycle Management (RCM) system. The team will lay the foundation for facilitating the exchange of (non clinical) data and money between Headway and payers. This team will also support other cross-functional initiatives like claims visibility and building scalable payer onboarding & relationship management.

Who you are

We’re looking for experienced engineering team leaders and people managers who are relationship obsessed, drive results and enable their teams to build for technical excellence. As an Engineering Manager at Headway, you will work closely with Engineering Leadership to help shape the future of the engineering organization. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact on our rapidly scaling engineering team.

  • Lead and manage a team of 6+ engineers
  • Help build out our engineering team as the headcount grows from 40 - 120+ over the next year
  • Ensure there is process and product alignment across your team
  • Develop and grow your team through weekly 1-1s, mentorship, and feedback
  • Work with and help develop aspiring engineering leaders within the engineering team
  • Contribute to the broader company strategy and product roadmap
  • Refine our Software Engineering hiring processes to meet the needs of our scaling organization

Below are some additional experiences we think help engineering managers succeed at Headway

  • You have 3-5+ years of experience as a Software Engineer
  • You have 3+ years of experience as an Engineering Manager
  • You have have a track record of working well across teams and functions
  • You have a track record of building and leading high performing teams that have effectively delivered business outcomes through technical investments
  • You have a strong technical foundation that allows you to ensure your team is making appropriate technical decisions
  • You have prior experience with Python and React, nice to have
  • You have experience working with AWS infrastructure
  • BS, MS in Computer Science or related field

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

  • Initial screen : You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background.
  • First rounds: You'll meet with an engineering leader and hiring manager on the team to go deeper into your technical and people leadership experiences
  • Final rounds : You’ll meet several more team members for one technical and multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway.
  • References and the Offer : Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

  • Salary information is based on a single salary target per role:
    • The starting salary for Engineering Managers is $195,500 and increases to $230,000 based on industry tenure and experience.
  • Benefits offered include:
    • Medical, Dental, and Vision coverage
    • HSA / FSA
    • 401K
    • Work-from-Home Stipend
    • Therapy Reimbursement
    • 16-week parental leave for eligible employees
    • Carrot Fertility annual reimbursement and membership
    • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
    • Unlimited PTO
    • Employee Assistance Program (EAP)
    • Training and professional development


We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem - across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.

Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please contact

Headway employees work remotely across the US, with the option to work from offices in New York City and San Francisco. Headway participates in E-Verify. To learn more, click here.

Job Summary
  • Job Title
    Engineering Manager
  • Company
  • Location
  • Employment Type
    Full time
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