Senior Engineering Manager (Web Platform)

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. 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 Web Platform Team at Headway

The web platform team's mission is to build Headway's capability to deliver a new mental healthcare system through web applications that can be rapidly developed, easily maintained, and provide high-quality user experiences. The team does this across three areas: maintaining and evolving the web platform (frameworks, build tooling, the Helix design system), defining and propagating front-end best practices (accessibility, performance, testing, maintainability), and facilitating product design workflows so that ideas move efficiently from concept to shipped product.

Every engineer at Headway builds on top of the web platform team's foundation. When the platform is strong, product teams move faster and ship with higher quality. As the platform evolves to incorporate agentic engineering workflows, the team is positioned to become an even greater multiplier: using agents to build front-end code directly in line with Headway's standards, reducing the time and cognitive load product teams spend on front-end concerns so they can focus on business logic and product outcomes.

Principles that guide us:

Focus on the mission : We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they're facing.

Ship small, learn fast : We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration

Everything is a product : Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.

Optimize for trust : We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

Languages: TypeScript

Libraries & Frameworks: React, Remix, Next.js

Monitoring: Datadog, PagerDuty, Sentry

Version Control: Github

AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

About this role

As a Senior Engineering Manager for Web Platform, you will be responsible for leading and growing the engineering team through people development, strategic planning, and close partnership with Engineering Leadership, Product, and Design. You will play a leading role in defining the team's roadmap, making a clear and well-supported case for platform investment across the organization, and ensuring the team's work directly enables Headway's product and business goals. This role requires strong organizational leadership and strategic communication: the platform only delivers its full value when the rest of engineering understands what it makes possible.

An engineering team : hiring to a high bar, growing the people on it, and setting the culture your team operates by

Platform maintenance and evolution : the web architecture, frameworks and libraries (React Router 7, Helix, Tailwind, Vite), and the Helix design system that all Headway web surfaces depend on

Best practices and standards : accessibility (WCAG 2.1 AA), performance, front-end testing, and maintainability; enabling product teams to focus on product capabilities rather than UI and framework details

Product design workflow : the collaboration with Design that turns Figma into a real component library and brings code prototyping into Headway's product development process, reducing friction at every stage from idea to shipped product

Organizational visibility and strategy : proactively making the case for platform investment through clear documentation, metrics, and executive communication; building alignment across Design, Product, and product engineering teams so the roadmap reflects real needs and delivers visible impact