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 70,000 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, GV, 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.

About the Developer Tooling team at Headway (Engineering Foundations)

The Developer Tooling team is part of Engineering Foundations at Headway. Engineering Foundations builds the core platforms, infrastructure, and AI-driven development systems that enable all engineers to build, test, deploy, and operate software with speed and reliability.

Developer Tooling focuses specifically on the day-to-day developer experience. Our customers are Headway’s engineers. We own the systems and workflows that directly impact developer velocity, confidence, and code quality, including CI/CD, test infrastructure, local development environments, observability, documentation tooling, and AI-powered developer workflows.

Our goal is simple and high impact. Reduce friction in the development lifecycle so engineers can spend less time dealing with flaky tests, broken environments, and opaque pipelines, and more time shipping high-quality product experiences for patients and providers.

Principles that guide us

Developer experience is a product. Internal tooling is treated with the same care and quality bar as customer-facing software.
Stability enables speed. Predictable pipelines and reliable feedback loops are prerequisites for velocity.
Automation over toil. Repetitive or manual work should be automated wherever possible.
Thoughtful AI adoption. AI is used to expand what engineers can do, not to replace judgment or craftsmanship.
Clear ownership. Reliable systems require explicit ownership, accountability, and fast feedback loops.

About this role

As Engineering Manager for Developer Tooling, you will lead a team responsible for the core developer experience at Headway. You will own strategy and execution for tooling and systems that every engineer relies on to build, test, and ship software.

A major focus of this role is advancing AI-powered developer productivity. You will help define how AI is used across engineering, from inner-loop coding assistance to agentic workflows for planning, testing, refactoring, documentation, and troubleshooting. This role is about enabling engineers to work more effectively at scale by making AI a trusted, integrated part of the development workflow.

You will operate within Engineering Foundations and partner closely with product engineering leaders and other platform teams. You will run tight feedback loops with the engineering organization, translate developer pain into durable improvements, and set clear standards for reliability, quality, and usability across shared tooling.

Who you are

A people-first engineering leader who cares deeply about developer experience
Technically credible and comfortable going deep on CI/CD, test systems, and developer tooling
AI-forward with hands-on experience using modern AI-assisted development tools
Pragmatic and outcome-oriented, with a bias toward shipping improvements that engineers feel quickly
A clear communicator who can align stakeholders and advocate effectively for platform investments

Experience we’re seeking

3+ years of experience managing software engineering teams
Experience owning developer tooling, platform infrastructure, or internal engineering systems
Strong understanding of CI/CD, test reliability, and local development workflows
Hands-on experience with AI-powered developer tools and interest in agentic workflows
Track record of improving developer velocity, reliability, or code quality at scale
Experience partnering with product engineering teams as internal customers

You’ll love this role if you want to

Shape how engineers across the company build software every day
Lead the adoption of AI as a first-class part of the development workflow
Eliminate flaky tests, unreliable CI, and broken local environments
Build tooling that compounds in value as the organization scales
Combine technical depth, people leadership, and org-level impact in a single role

Compensation and Benefits:

The expected base pay range for this position is $198,000-$237,500, 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.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

Equity compensation
Medical, Dental, and Vision coverage
HSA / FSA
401K
Work-from-Home Stipend
Therapy Reimbursement
16-week parental leave for eligible employees
Carrot Fertility annual reimbursement and membership
13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training and professional development

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.

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 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.