Exceptional People + Purpose Beyond Profit = Watershed Outcomes

Exceptional People + Purpose Beyond Profit = Watershed Outcomes

Technical Support Engineer



IT, Customer Service
Posted on Tuesday, November 7, 2023

Headway is building a new mental healthcare system that everyone can access. We make it easy for people to find quality in-network mental health care by removing historic barriers faced by mental health providers, payers, and patients.

1 in 4 people in the US have a treatable mental health condition, but the vast majority do not get the care they need. The primary reason is cost: the majority of therapists do not accept insurance, meaning paying for therapy is prohibitively expensive. This is where we got our start – Headway has built the first software-enabled national network of therapists who accept health insurance, making it possible for patients to find quality care they can afford and enabling mental healthcare providers to grow their practice.

We launched in April of 2019 and are now powering 500,000+ appointments a month. To scale our vision, we’ve raised over $225+ million in funding from a16z, Thrive, Accel, Spark Capital, Google Ventures, Andreessen Horowitz and Health Care Services Corporation.

Join us, and make an impact

Headway is looking for a Technical Support Engineer to help us get closer to executing our mission: to create access to affordable, quality mental healthcare across the United States. As a Technical Support Engineer, you will make a direct impact on Headway providers and patients every day. The Technical Support team is part of our Engineering team, and you will be working alongside our Customer Experience team, Growth team and other stakeholders within the company in order to provide an exceptional user experience. Your primary role will be investigating and resolving technical issues that our customers face. This will require you to run database queries, review our codebase and collaborate with software engineers if necessary, and where possible push fixes. Additionally, you will be working on building processes and writing documentation to help your colleagues on the TSE team and educate cross-functional teams and assist them in their day-to-day operations.

You will:

  • Support our Customer Experience and sales team to help resolve issues and requests that require technical support
  • Investigate and fix bugs affecting our users’ experience
  • Work on tooling and processes to help the Customer Experience team deliver the best possible support to our users
  • Be the technical voice of the customer to help get high impact solutions shipped
  • Shape what being a TSE at Headway means and help grow the team

You will love this role if:

  • You are comfortable reading and writing code (bonus points for Python and/or React)
  • You are proficient in SQL
  • You can effectively communicate complex technical scenarios to people with less technical knowledge
  • You love tracking down bugs -- and you are determined to squash them!
  • You are extremely detail oriented
  • You love diving into new technologies, products and systems to become an expert
  • You are comfortable with ambiguity and enjoy operating with a high degree of autonomy

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.
  • Take home assignment: You’ll complete a take home assignment in which you can demonstrate your troubleshooting and communication skills.
  • First round: You'll meet with a Technical Support Engineer on the team to do some live coding and learn more about the engineering team.
  • Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave 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 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 Technical Support Engineers is $85,000 and increases to $146,625 based on industry tenure and experience.
  • Benefits offered include:
    • Medical, Dental, and Vision coverage
    • HSA / FSA
    • 401K
    • Work-from-Home Stipend
    • Therapy Reimbursement
    • 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 employees work remotely across the US, with the option to work from offices in New York City and (coming soon!) San Francisco. Headway participates in E-Verify. To learn more, click here.