This role is ideal for a senior-level engineering leader with at least 3 years of management experience who is passionate about developer productivity. The foun
Work type: remote
Location: New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United States
Salary: $198,000 – $237,500/yr
Type: Full-time
This role is ideal for a senior-level engineering leader with at least 3 years of management experience who is passionate about developer productivity. The foundation of this role is technical credibility in CI/CD, test infrastructure, and local development environments. Importantly, they are looking for an "AI-forward" leader who has hands-on experience integrating AI-assisted tools and agentic workflows into the software development lifecycle. The position offers a highly competitive salary ($198k–$237.5k) plus equity and a robust benefits package, including unique perks like therapy reimbursement and a "holiday break" week. As a Series D company with significant funding, this is an opportunity to scale the engineering culture of a mission-driven organization while working fully remote from major US hubs. **You might be a good fit if you:** * Have managed internal platform or tooling teams and view "developer experience" as a product. * Are excited about moving beyond basic Copilot usage to build automated, AI-driven workflows for testing and refactoring. * Prioritize eliminating "toil" like flaky tests and opaque pipelines to improve team velocity. * Enjoy partnering with product engineering teams to translate their pain points into durable infrastructure improvements.
Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.
1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.
Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
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
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
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.