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 Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

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.

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.

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 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.