Engineering Manager (Provider)

CHART EM: Responsible for ensuring providers have the tools they need to efficiently document their clinical care. This is one of Headway's most AI-intensive product areas: from session transcript-to-note generation and AI-powered clinical summaries that give providers their time back, to intelligent tools for psychiatrists managing patient medications — this team is redefining what clinical documentation looks like when AI does the heavy lifting.

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.

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.

Lead and manage an engineering team focused on provider acquisition and growth (starting with 2–3 engineers and scaling over time)

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

Collaborate with the Onboarding team to ensure a seamless end-to-end provider experience from first touch to first appointment

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?

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

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 experiences.

Final rounds: You'll meet team members across product and engineering leadership for multiple behavioral interviews, and a technical interview (System Design), leaving you with a fuller picture of what it's like to work at Headway.

References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!