Senior Software Engineer

Summary

Join Headway's Trust Foundations team as a Senior Software Engineer and contribute to building a secure and reliable mental healthcare system. You will design, build, and operate core trust primitives, embed security and privacy by design, scale identity rails, and deliver scalable platform foundations. The role involves translating open standards into scalable building blocks, mentoring engineers, and championing operational excellence. You will need 5+ years of professional software engineering experience, proven systems architecture leadership, and deep expertise in either Identity and Access or Platform Engineering. Headway offers a competitive salary, equity compensation, comprehensive benefits, and a remote-work option.

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

Responsibilities

• 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

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