Senior Software Engineer; Trust Foundations

About this role:

Building for trust is non‑negotiable in our mission of making mental healthcare more accessible and affordable across the US: patients share sensitive information, payers demand demonstrably strong controls, and providers depend on reliable, secure infrastructure.
Trust Foundations is responsible for instilling confidence in our products by safeguarding our user’s data. We achieve this by developing out‑of‑the‑box identity, access, and secure‑data platforms for other engineering teams to utilize. Our mission is to make the most secure path the most efficient path, enabling clinicians, patients, and payers to trust Headway implicitly.

• Design, build, and operate core trust primitives - authentication providers, authorization engines, stratified encrypted data stores, and tamper‑evident telemetry.
• Embed security & privacy by design – Codify guardrails in linting rules and CI, and partner with Legal/Compliance to translate regulatory language into concrete engineering controls.
• Scale our identity rails – Design and evolve multi‑tenant authentication & authorization services that handle millions of sessions daily with high availability expectations.
• Deliver scalable, secure platform foundations – Build shared services that embed security‑by‑default (least‑privilege access, encryption in transit and at rest, audit hooks) and expose intuitive APIs so product teams can move quickly without compromising trust.
• Turn ambiguous requirements into incremental delivery plans – Lead architecture reviews; break large problems into testable milestones; and make pragmatic build‑vs‑buy decisions in a regulated domain.
• Champion operational excellence – Instrument services, tune alerting, own on‑call runbooks, and drive post‑incident hardening.
• Elevate engineering culture – Mentor teammates, document patterns, and help recruit the next generation of Headway engineers.

• 5+ years of professional software engineering with a strong command of at least one modern language (we use Python3 and Type Script).
• Proven systems‑architecture leadership - you have shaped requirements, led cross‑team roadmaps, and delivered complex backend or platform services at scale.

Deep expertise in one of two focus areas:

• Identity and Access - demonstrated experience working with third party IdPs, expertise with OAuth
  2.0/OIDC standards, have implemented step‑upMFA and common RBAC frameworks.
• Platform Engineering (scalable, secure foundations) - demonstrated experience building high‑throughput, fault‑tolerant services that bake in security‑by‑default patterns, provide clear developer interfaces, and enable downstream teams to move faster.
• A track record of mentoring engineers
  , elevating design quality, and improving engineering processes.
• Sound build‑vs‑buy judgment and the ability to collaborate with product, legal, and operations in a highly regulated environment.

The expected base pay range for this position is $164,900 - $233,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance‑based variable compensation and an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

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
• Flexible 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 inform the recruiter when they contact you to schedule your interview.

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