Engineering Manager, Headway

• 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

Desirable

• We’re looking for experienced engineering team leaders and people managers who are relationship-obsessed, drive results and enable their teams to build for technical excellence. As Engineering Manager of the Web Platform Pod, you will:
• 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
• This is an opportunity to shape the future of 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

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background
• First rounds: You'll meet with an engineering leader on the team to go deeper into your technical and people leadership experiences
• Final rounds: You’ll meet several more team members for one technical and multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!