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.

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 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, 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.

Responsibilities

• Lead and grow the engineering team through people development and strategic planning.
• Define the team's roadmap and make a clear, well-supported case for platform investment across the organization.
• Ensure the team's work directly enables Headway's product and business goals.
• Build alignment across multiple product teams, navigating competing priorities, and driving a shared roadmap forward.
• Create organizational visibility for your team's work through documentation, metrics, and stakeholder engagement.
• Maintain strong cross-functional relationships with Design and Product, keeping platform and product roadmaps in sync.

Qualifications

• 5+ years of experience as an Engineering Manager.
• 10+ years of experience as a Software Engineer, with depth in modern frontend and web technologies.
• Experience leading platform, infrastructure, or developer experience teams and understanding how to make the case for foundational work in an organization driven by product outcomes.
• Strong strategic communicator who can translate platform investments into clear business value for non-technical stakeholders and executive leadership.
• Proactive in creating organizational visibility for your team's work through documentation, metrics, and stakeholder engagement.

Pay

Compensation Range: $261,200 - $331,500