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 85,000 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

Web Platform owns how Headway builds our frontend applications, including the UX. Web Platform sits in our Engineering Foundations organization, alongside our infrastructure and reliability team and our agentic engineering team. Every engineer who builds for the web at Headway builds on top of our work. 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.

The team works across three areas:

• Design system: Helix is the shared language between Design and Engineering. Its components, tokens, and patterns keep what we design and what we ship the same across every Headway web app.
• Web architecture: We give engineers one clear way to build a Headway web app. This covers frameworks, build tooling, data loading, testing, performance, and accessibility across our patient, provider, internal, and marketing apps.
• Agentic UI: Headway engineers build with AI agents every day. We want those agents to build UI to Headway's standards by default. That takes a design system, patterns, and docs that agents can read, plus automated checks (visual regression, accessibility, and design system conformance) so that agent-written UI ships with confidence.

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 therapists 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, React Router 7, Vite, Tailwind CSS, and Helix (our design system)
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: GitHub
• AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

About this role

As the Senior Engineering Manager for Web Platform, you'll lead a small, senior team of five frontend engineers and own the vision for how Headway builds UI. This is the only role of its kind at Headway. You'll set the strategy for our design system and our web architecture, and you'll be the voice of frontend engineering across the company. The team doesn't have a dedicated product manager, so you'll set the roadmap with Design leadership and Engineering Foundations leadership, and you'll show the value of the work with clear metrics.

You'll stay close to the code. We expect you to be comfortable opening PRs, reading and changing code with AI tools, and taking on small pieces of work yourself, especially in your first few months. Larger projects stay with the team.

What you'll own

• Your team: Hire to a high bar, grow each person on purpose, and address underperformance directly. Give senior engineers ownership of technical direction, and make sure the team works as one team across all of its areas.
• Vision and strategy: Hold a clear, opinionated view of where Headway's frontend is going, and explain it to engineers, designers, and executives. Connect it to the Engineering Foundations strategy and to product roadmaps, and change it when the evidence says to.

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