Engineering Manager (Developer Tooling)

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.

• 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.
  
  

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.

• 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
  
  

• 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
  
  

• 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