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