Headway is building a new mental healthcare system that everyone can access.

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 for prospective patients. That’s why Headway is building the first software-enabled network of therapists who accept health insurance, making it easy for therapists to grow their practices, and possible for patients to find quality care they can afford.

We launched in April of 2019 and are now powering 175,000+ appointments per month. To scale our vision, we’ve raised over $100 million in funding from a16z, Thrive, Accel, and Google Ventures.

Join us, and make an impact.

About the role

As Headway’s founding Security Engineer, you’ll have the unique opportunity to be the builder and driver of our dedicated, in-house Security engineering team. This role reports to our Head of Infrastructure and will partner with them to design our next-generation security program, touching all aspects of Headway’s business and systems. You will both technically and organizationally lead security projects ranging from practice changes to technical architecture to security infrastructure development to penetration testing. You will bring clarity to the next two years of security-focused work, and help to further build out the team, including adding needed expertise and bandwidth over the next 12 months.

Tools we use:

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

Who you are:

  • You have technical experience with implementing secure platforms and products at a deep level.
  • You want to instill a culture of secure development across engineering and lead the organization to embrace security as a part of normal development.
  • You can understand the business stage as well as the security risk and work with leadership to understand and decide on tradeoffs and priority.
  • You are an avid mentor and seek to teach others how to improve while enabling them to succeed.
  • While operating as a leader in some respects, you are still technical and enjoy tackling deep problems and producing technical solutions and automation.

Experience we’re seeking:

  • 5+ years experience in security and/or software engineering roles
  • Web/API platform penetration testing experience
  • Broad security domain knowledge and common application vulnerabilities
  • Experience with cloud hosted environments and patterns for secure architecture in the cloud
  • The ability and drive to continuously educate yourself and others

You’ll love this role if you want to:

  • Change the trajectory of a startup striving to redefine access to mental health in America
  • Work on a highly collaborative, cross-functional engineering team in order to build the best and most secure products for therapists, patients, physician and payer partners, and/or your teammates at Headway
  • Help establish and engrain best practices throughout our organization
  • Contribute to our engineering culture, processes, and documentation with the same thought and care that we do our software (one of our engineering cultural principles is “Everything is a Product”)

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 round: You'll meet with our Head of Infrastructure to dig deeper into the role and requirements, and illustrate your technical, operational and leadership experiences.
  • 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 of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

#LI-AC1

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 our NYC HQ.

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 to receive other benefits and privileges of employment, please contact talent@findheadway.com.


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Headway is building a new mental healthcare system that everyone can access.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.

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