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.

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.

• 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.

• 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.

• 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)

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.

• 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.

• Design system and Design partnership: Evolve Helix with Design leadership as shared owners. Make the path from a design to production code short, so that designers and engineers start from the design system.

• Web architecture and standards: Own the frameworks and tooling that every Headway web app depends on, and the standards for accessibility (WCAG 2.1 AA), performance, testing, and maintainability.

• Agentic UI: Give agents the skills, docs, and guardrails they need to write good frontend code. Build the automated checks and agent reviews that let that code ship with confidence.

• Frontend community: Grow our frontend guild at Headway. Learn from product engineers what's broken, and turn it into the roadmap.

• Priorities and headcount: Decide among planned work, support requests, and new bets, and keep the team from becoming a help desk. Make the case for the team size that Headway's frontend needs.

• You've built your career in frontend. You were a senior or staff frontend engineer before you moved into management, and you have deep experience with React and the modern web.

• You've led a frontend platform, design system, or web architecture team, ideally at a fast-growing company.

• You've managed engineers for [3+] years. You've hired, grown senior engineers, and managed performance, including turning around or moving out someone below the bar. You don't need experience managing managers.

• You use AI every day. You've shipped code with AI tools in the last six months, at work or in your own projects, and you have a view on how agents should build UI.

• You have a clear point of view on what great frontend engineering looks like today, and you advocate for it with data. You can explain the value of platform work to product teams and to executives.

• You work closely with Design. You understand how designers work, and you can turn design system decisions into engineering plans.

• You've built alignment across several product teams with competing priorities, and kept a shared roadmap moving.

• You like a fast pace. Most of your plans are measured in weeks or a few months.

After you apply to Headway, here are some details of what to expect during the interview process.

• 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 the hiring manager to go deeper into your team and people leadership experience, and you'll do a frontend AI coding interview.

• Final rounds: You'll meet people across engineering, product, and design leadership. Expect behavioral interviews on people leadership and on partnership with Design, a product sense interview, and frontend technical interviews on system design [and technical depth].

• 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!

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.