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

• Agentic engineering integration : evolving the team's operating model to use agentic workflows for higher-leverage work, enabling contributors across Headway to build in line with platform standards without requiring deep front-end expertise

Who you are

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 a Senior Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Design, and Business teams to help shape the future of the engineering organization. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact on our rapidly scaling engineering team.

Below are additional experiences we think help engineering managers succeed at Headway:

• You have 5+ years of experience as an Engineering Manager

• You have 10+ years of experience as a Software Engineer, with depth in modern frontend and web technologies

• You have experience leading platform, infrastructure, or developer experience teams and understand how to make the case for foundational work in an organization driven by product outcomes

• You are a strong strategic communicator who can translate platform investments into clear business value for non-technical stakeholders and executive leadership

• You have a track record of building alignment across multiple product teams, navigating competing priorities, and driving a shared roadmap forward

• You are proactive in creating organizational visibility for your team's work through documentation, metrics, and stakeholder engagement, not just through the work itself

• You are able to build and maintain strong cross-functional relationships with Design and Product, keeping platform and product roadmaps in sync

Our interview process

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 with an engineering leader on the team to go deeper into your team and people leadership experiences.

• Final rounds: You'll meet team members across product and engineering leadership for multiple behavioral interviews and two technical interviews (System Design & AI Coding), 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!

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.

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