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!

• Work from home opportunities

Total funding: $327m

1 in 4 US citizens are currently living with treatable mental health conditions, however, a vast majority of people are unable to access the care they need, the primary reason being cost. Headway connects clients with therapists who accept insurance as payment and provides independent practitioners with the tools and resources needed to serve their patients and manage administrative workloads.