Senior Software Engineer, Trust Foundations

Position Overview

Headway's mission is to build a new mental health care system that everyone can access. We have developed a software-enabled national network of providers that helps people find therapists who accept insurance. Currently, a significant portion of the US population faces barriers to mental healthcare due to the high cost, as most providers do not accept insurance. Headway aims to solve this by making it easier for therapists to accept insurance and grow their practices.

Founded in 2019, Headway has grown into a national network of over 45,000 mental healthcare providers across all 50 states. Our software supports these providers, and we have served over 1 million patients. We are a Series D company with over $325 million in funding from prominent investors including a16z, Accel, GV, Spark Capital, Thrive Capital, Forerunner Ventures, and Health Care Service Corporation. We are committed to making your time here the most meaningful experience of your career and invite you to join us in transforming mental healthcare.

About the Trust Foundations Team

Building trust is paramount to our mission of making mental healthcare accessible and affordable. Patients share sensitive information, payers require robust controls, and providers rely on secure infrastructure. The Trust Foundations team is responsible for building confidence in our products by safeguarding user data. We achieve this by developing out-of-the-box identity, access, and secure-data platforms for other engineering teams. Our goal is to make the most secure path the most efficient path, fostering implicit trust from clinicians, patients, and payers.

As a Senior Software Engineer on the Trust Foundations team, you will write production code daily and contribute to 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 our work, and mentor engineers across the company on trust-first thinking.

Responsibilities

• Design, build, and operate core trust primitives, including authentication providers, authorization engines, stratified encrypted data stores, and tamper-evident telemetry.
• Embed security and privacy by design by codifying guardrails in linting rules and CI, and partnering with Legal/Compliance to translate regulatory language into concrete engineering controls.
• Scale our identity rails by designing and evolving multi-tenant authentication and authorization services that handle millions of sessions daily with high availability expectations.
• Deliver scalable, secure platform foundations by building shared services that embed security-by-default (least-privilege access, encryption in transit and at rest, audit hooks) and expose intuitive APIs, enabling product teams to move quickly without compromising trust.
• Turn ambiguous requirements into incremental delivery plans by leading architecture reviews, breaking down large problems into testable milestones, and making pragmatic build-vs-buy decisions in a regulated domain.
• Champion operational excellence by instrumenting services, tuning alerting, owning on-call runbooks, and driving post-incident hardening.
• Elevate engineering culture by mentoring teammates, documenting patterns, and helping recruit the next generation of Headway engineers.

Requirements

• 5+ years of professional software engineering experience with a strong command of at least one modern language (we use Python 3 and TypeScript).
• Proven systems-architecture leadership, including shaping requirements, leading cross-team roadmaps, and delivering complex backend or platform services at scale.
• Deep expertise in one of the following focus areas:
  • Identity and Access: Demonstrated experience working with third-party IdPs, expertise with OAuth 2.0 / OIDC.
  • (Note: The original prompt was cut off here, so the second focus area is missing.)

Company Information

Headway is on a mission to build a new mental health care system everyone can access. We have built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. We are a Series D company with significant funding and a growing team dedicated to making a meaningful impact on mental healthcare in the US.