Engineering Manager

Summary

Join Headway's Engineering Foundations Group as an Engineering Manager for the Web Platform Pod and lead the standardization and scaling of web development. You will set the vision and strategy, lead and grow a high-impact team, drive adoption of best practices, and develop experimentation frameworks. Collaborate with cross-functional partners to understand user needs and ensure exceptional platform value. This role offers the opportunity to shape Headway's web development ecosystem and make a lasting impact in a fast-paced environment. Your leadership will directly influence Headway's mission, engineering velocity, and developer experience. Headway offers competitive compensation and benefits, including equity, comprehensive health coverage, parental leave, and professional development opportunities.

Requirements

• 4+ years of people management experience in an engineering leadership role, with prior experience in frontend or fullstack engineering
• Experience leading cross-functional teams and working collaboratively with product, design, and other engineering teams
• Ability to mentor and guide engineers, fostering technical excellence and a culture of continuous learning
• Passionate about building scalable, reliable, and maintainable systems that abstract complexity and empower teams
• Strong technical intuition—able to navigate and discuss engineering tradeoffs related to timelines, resources, and long-term maintainability
• Deep understanding of modern web technologies, including their strengths, tradeoffs, and best practices
• Experience designing and building frontend infrastructure and platform capabilities to support scalable web applications
• Strong foundation in performance optimization, observability, and security practices for web applications
• Experience with frontend testing strategies (e.g., unit, integration, and end-to-end testing) and CI/CD automation for web applications
• Comfortable with ambiguity and thrives in a fast-paced, high-growth environment
• BS, MS in Computer Science or related field

Responsibilities

• Set the vision and strategy for how web development is standardized and scaled at Headway
• Lead and grow a high-impact team, fostering a culture of excellence, collaboration, and innovation
• Drive adoption of best practices across all product engineering teams, ensuring high-quality, accessible, and scalable web applications
• Develop and maintain experimentation frameworks, providing engineers and product teams with the tools to run A/B tests, gradual rollouts, and controlled experiments
• Collaborate with cross-functional partners (Eng, Product, Design, Growth, Customer Success) to deeply understand user needs and ensure the platform delivers exceptional value
• Measure and improve impact by defining KPIs, gathering feedback, and iterating on platform capabilities

Preferred Qualifications

• Hands-on experience with A/B testing, feature flagging, and experimentation frameworks
• Familiarity with modern web stacks (e.g., React, Next.js, TypeScript) and frontend build systems
• Experience in developer productivity tooling, including performance monitoring, automated testing, and CI/CD pipelines
• Knowledge of progressive web apps (PWAs), accessibility standards (WCAG), and SEO best practices
• Experience with cloud platforms (AWS, GCP) and edge computing/CDN strategies for frontend performance

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