Engineering Manager (Provider)

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Engineering Manager (Provider)

About Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide.

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 & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js

Datastores: Postgres, Redis

Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka

Monitoring: Datadog, PagerDuty, Sentry

Version Control: Github

Vulnerability Management: Snyk, Semgrep

Cloud Security: Lacework

AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

About these roles

At Headway, we're building a national network of therapists who accept insurance — and making mental healthcare radically more accessible in the process. Supporting providers isn't just about connecting them with patients — it's about delivering the tools they need to manage their practice with ease, confidence, and compliance.

Our providers are the heart of Headway's mission — and empowering them with an easy-to-use platform is critical to both their success and the quality of care patients receive. Whether it's saving providers time, simplifying documentation, or ensuring compliance, this role is at the center of our providers' lives. As an engineering leader at Headway, you will be responsible for leading and growing the engineering pods behind our provider experiences through people development, strategic planning, and hands-on technical support or guidance. You get to play a leading role in defining what and how these teams build, setting up how the teams operate, support, and ultimately drive best-in-class user experiences that have a measurable impact on our ability to execute and meet the demands of a high growth startup.

We are hiring for 2 Engineering Managers within the Provider group:

CHART EM: CHART owns the clinical documentation backbone every provider touches — progress notes, treatment plans, assessments, and session confirmations — plus e-prescribe, a greenfield product bringing prescribing directly into Headway for the first time. This is a 0→1 team with real runway to shape the roadmap, not inherit a finished system: AI-assisted documentation is a near-term focus, correctness is non-negotiable because the platform doesn't work without it, and the work sits at the intersection of clinical outcomes and engineering excellence — ideal for someone who wants complex domains, high-stakes correctness, and greenfield product work with direct patient impact.

Group Practices EM: Group Practices represents a substantial portion of our provider network and have specific needs to run their practice. This team is responsible for continuing to grow the Group Practices segment and enabling group practice providers and their administrative staff to operate efficiently on Headway.

Who you are

We're looking for experienced engineering team leaders and people managers who are product-minded, data-informed, and energized by growth. As an Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Marketing, RevOps, and Design to shape the future of our provider acquisition strategy. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact at a high-growth company.

Partner closely with cross-functional stakeholders to build systems that enable rapid experimentation and long-term scale

Drive alignment across your team on process, prioritization, and product outcomes

Develop and grow your team through weekly 1-1s, mentorship, and feedback

Work with and help develop aspiring engineering leaders within the engineering team

Contribute to the broader company strategy and product roadmap

Leads Teams into the AI Era: You don't just tolerate AI tools — you actively shape how your team uses them. You've thought carefully about where AI accelerates engineering work and where it doesn't, and you help your engineers develop genuine fluency rather than surface-level familiarity. Whether it's AI-assisted code review, LLM-powered features, or rethinking which workflows to automate, you bring a builder's mindset: what should we automate, what should stay human, and how do we ship it responsibly in a healthcare context?

Below are additional experiences we think help engineering managers succeed at Headway:

You have 3+ years of experience as an experienced Engineering Manager

You have 3-5+ years of experience as a Software Engineer

You're energized by experimentation and growth — and can balance short-term learning with long-term scale

You have a strong product mindset and have built strong cross-functional relationships that drive optimal user experiences and build trust with users

You have a strong technical foundation that allows you to ensure your team is making appropriate technical decisions

You have a track record of building and leading high performing teams that have effectively delivered business outcomes through technical investments

You have a track record of working well across teams and functions

Nice to have: Prior experience with Python and React and working with AWS infrastructure

Nice to have: Experience in health tech, building user-facing products

Nice to have: Experience building or managing teams that ship AI-powered product features — particularly in high-trust domains like clinical tools or financial systems

BS, MS in Computer Science or related field

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

Initial screen: You'll connect with someone in recruiting so you can learn more about the team, Headway's mission and exciting growth, and we can get a better idea of your background.

First rounds: You'll meet with an engineering leader on the team to go deeper into your team and people leadership experience. You'll also complete an AI Coding round — a collaborative session where we're less focused on syntax and more on how you think th