Senior Software Engineer

At Headway, our mission is to revolutionize mental health care, making it accessible to everyone. We've developed technology that connects individuals with excellent therapists through the first software-enabled national network of providers that accept insurance.

In the United States, 1 in 4 individuals suffers from a treatable mental health condition, yet many providers do not accept insurance, leading to high therapy costs. Headway is committed to creating a new mental healthcare system that everyone can access, streamlining the process for therapists to accept insurance and expand their practices.

Founded in 2019, Headway has grown into a diverse network of over 60,000 mental healthcare providers in all 50 states, delivering services to over 1 million patients. Backed by influential investors, Headway is a Series D company, having raised over $325 million. We want your time at Headway to be the most meaningful experience of your career. Join us in transforming mental healthcare for the better

About this role:

Building trust is essential to our mission of making mental healthcare accessible and affordable. At Headway, we recognize the importance of safeguarding users' data, as patients share sensitive information, payers require robust controls, and providers rely on secure infrastructure. The Trust Foundations team is vital in establishing confidence in our products. We create comprehensive identity, access, and secure-data platforms for use by other engineering teams. Our goal is to ensure that clinicians, patients, and payers can trust Headway completely.

We are expanding our team and hiring for multiple positions at both mid and senior levels. As a Software Engineer/Senior Software Engineer on the Trust Foundations team, you will write production code daily and help shape the future vision for trust at Headway. You will implement open standards like OAuth2.0/OIDC, RBAC/ABAC, and envelope encryption into scalable components, incorporate privacy-by-design principles, and mentor engineers across the organization to adopt a Trust-first mindset.

Your responsibilities will include:

• Designing, building, and operating core trust primitives such as authentication providers, authorization engines, stratified encrypted data storage, and tamper-evident telemetry.
• Embedding security and privacy by design - Codifying guardrails in linting rules and CI while collaborating with Legal/Compliance to translate regulatory requirements into concrete engineering controls.
• Scaling our identity infrastructure - Developing multi-tenant authentication and authorization services that manage millions of sessions daily with high availability demands.
• Delivering scalable, secure platform foundations - Building shared services that incorporate security by default (least-privilege access, encryption both in transit and at rest, and audit hooks) and provide intuitive APIs for product teams to innovate quickly without sacrificing trust.
• Transforming ambiguous requirements into actionable plans - Leading architecture reviews, breaking down large challenges into manageable milestones, and making pragmatic build vs. buy decisions in a regulated environment.
• Championing operational excellence - Instrumenting services, optimizing alerting, managing on-call runbooks, and driving improvements after incidents.
• Enhancing engineering culture - Mentoring teammates, documenting best practices, and assisting in recruiting the next generation of Headway engineers.

To be successful in this role, you should have:

• 5+ years of professional software engineering experience with expertise in at least one modern programming language (we primarily use Python3 and TypeScript).
• Proven leadership in systems architecture - You have shaped requirements, led cross-team initiatives, and delivered complex backend or platform services at scale.

Deep expertise in one of the following areas is essential:

• Identity and Access - Demonstrated experience with third-party IdPs, expertise in OAuth2.0/OIDC standards, and implementation of step-up MFA and common RBAC frameworks.
• Platform Engineering - Proven experience in building high-throughput, fault-tolerant services that implement security by default patterns and provide clear developer interfaces to enhance team velocity.

• A track record of mentoring engineers, improving design quality, and refining engineering processes.
• Sound judgment in build vs. buy decisions and collaboration with product, legal, and operations within a highly regulated context.

About Engineering at Headway:

Building a new mental healthcare system is achievable thanks to our engineering team's expertise. We are a small but talented group leveraging technology to shape the future, all while enjoying the journey

Our guiding principles include:

• Mission-driven focus - We see software as a means to create change, not as an end goal. Our software empowers patients and therapists to address their challenges effectively.
• Quick iterations - We believe rapid shipping and iteration help us understand user needs better.
• Product mindset - Every feature, from patient search to developer productivity improvements, is treated as a product with an end-user focus.
• Trust optimization - We prioritize continuous learning and ensure engineers feel safe to ask questions and address mistakes.

Technologies we utilize include:

• Languages: Python 3, TypeScript
• Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js
• Infrastructure: AWS (Fargate, ECS, S3), Spark, and Kafka
• Version Control: GitHub, PagerDuty
• Vulnerability Management: Snyk, Semgrep

After you apply to join Headway, you can expect the following interview process:

• Initial Screening: Connect with a recruiter to learn more about the team, Headway’s mission, and exciting opportunities.
• First Round: Engage in live coding with a team engineer and explore more about the engineering environment.
• Final Rounds: Meet additional team members for both technical and non-technical interviews for a comprehensive understanding of the work culture at Headway.
• References and Offer: The most exciting part We'll share all offer details, including equity specifics, alongside congratulations from eager future colleagues

Compensation and Benefits:

The anticipated base salary for this position ranges from $164,900 to $233,000, depending on qualifications, experience, and location. In addition to base salary, the role may include performance-based compensation and equity opportunities. We strive to provide a comprehensive rewards package, including notable health and wellness benefits, retirement options, and meaningful employee equity.

Our benefits include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• Health Savings Account/ Flexible Spending Account
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16 weeks of parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays annually, plus a Holiday Break between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

Headway believes in the strength of its people and recognizes that our mission cannot be achieved without a team that reflects diversity across various dimensions. We value inclusion and are committed to ensuring reasonable accommodations during the hiring process for individuals with disabilities.

Headway participates in E-Verify.

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