Engineering Manager (Developer Platform)

Headways mission is a big one to build a new mental health care system everyone can access. Weve 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 dont 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 weve grown into a diverse national network of over 60000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. Were 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 Headways 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 were 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
  
  

Youll 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 $198000-$237500 based on a variety of factors including qualifications experience and geographic 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 teams 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.

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