Senior Software Engineer - Trust Foundations, Identity and Platform

Job Description:

• 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.
• As a Senior Software Engineer on our Trust Foundations team, you’ll write production code every day while shaping the long‑term vision for trust at Headway.
• You will translate open standards - OAuth 2.0 / OIDC, RBAC/ABAC, envelope encryption - into scalable building blocks; embed privacy‑by‑design and reliability principles into everything we build; and mentor engineers across the company in Trust first thinking.
• 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.

Requirements:

• 5 + years of professional software engineering with a strong command of at least one modern language (we use Python 3 and TypeScript).
• 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‑up MFA 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.

Benefits:

• Equity Compensation
• 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

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