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 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 through problems and work with AI tools in a technical context.
Final rounds: You'll meet team members across product and engineering leadership for multiple behavioral interviews and one more 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!
Compensation
The expected base pay range for this position is $222,800 - 278,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.
COMPREHENSIVE BENEFITS
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
Headway participates in E-Verify. To learn more, click here. https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf
A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com http://findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.
