Engineering Manager (Developer Platform)

Headway•San Francisco, NY

15h•$198,000 - $237,500

About The Position

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 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

Requirements

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

Responsibilities

Lead a team responsible for the core developer experience at Headway.
Own strategy and execution for tooling and systems that every engineer relies on to build, test, and ship software.
Advance AI-powered developer productivity.
Define how AI is used across engineering, from inner-loop coding assistance to agentic workflows for planning, testing, refactoring, documentation, and troubleshooting.
Enable engineers to work more effectively at scale by making AI a trusted, integrated part of the development workflow.
Operate within Engineering Foundations and partner closely with product engineering leaders and other platform teams.
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.

Benefits

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