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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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 the role 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 scheduling, or ensuring compliance, this role is at the center of our providers' lives. As an engineering leader at Headway, you will be responsible for growing the team through people development, strategic planning, and hands-on technical support or guidance. You get to play a leading role in defining what and how the team builds, setting up how it operates, supports, and ultimately drives best-in-class user experiences that have a measurable impact on our ability to execute and meet the demands of a high growth startup. Practice Management is a new team inside Provider Experience, forming in Q4 2026 to own the tools providers use every day to run their practice: calendar, messaging, notifications, and the home page of our EHR. Most of our providers are solo practitioners, and running a whole practice on Headway means these pieces need to feel like one product. That is a core step toward our vision of being the AI-native EHR that insurance-based mental health providers run their whole practice on. As the EM, you will lead a team of engineers, work alongside a design lead and a PM, write the team's charter and roadmap from scratch, and partner closely with the other Provider Experience teams, Design, Clinical, and Marketing. 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 Softw