Senior Engineering Manager (Trust Foundations - Data Security)

About Headway

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 45,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About this role

Building for trust is non-negotiable in our mission of making mental healthcare more accessible. Fundamental to this is safeguarding our users' sensitive data. The Trust Foundations team is responsible for building the secure, auditable, and privacy-first platforms that all of Headway’s product teams rely on to innovate safely and quickly.

As the Senior Engineering Manager for our new Secure Defaults pod, you will own the vision for and lead the team tasked with protecting Headway's most sensitive data. You will be responsible for setting the long-term strategy for how we handle data security at scale, spearheading foundational initiatives in data lineage, classification of sensitive information (PHI), and building the next generation of our Role-Based Access Control (RBAC) primitives. A key, forward-looking part of this role will be to define the roadmap for the secure and compliant use of AI at Headway.

This is a critical leadership role for a passionate, mission-aligned engineering leader to build a new team and make an immediate impact on Headway’s ability to scale securely.

Principles that guide us

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they’re facing.
• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use

• Languages: Python 3, TypeScript
• Libraries: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark, Flink, and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework

Who you are

As a Senior Engineering Manager on the Trust Foundations team at Headway, you're a security-minded leader passionate about developing engineers and fostering a culture of technical excellence, collaboration, and results. You lead from the front, taking full ownership of your team’s roadmap and strategy. Comfortable diving into the technical details, you will guide your team with dedicated mentorship while staying relentlessly focused on building products that deliver real value to our users.

In this role, you will:

• Lead, develop, and mentor a team of 5+ engineers, guiding their career growth through con