Staff Technical Program Manager

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 TPM at Headway:

Join Headway's Engineering team as a Staff Technical Program Manager —a pivotal role where you'll define how we execute our most critical technical initiatives. You'll be the strategic thought partner who transforms complex, cross-functional challenges into clear execution plans that deliver topline business impact on our most critical company OKRs.

Primarily partnering with our Insurance team, you'll lead key programs that touch nearly every aspect of our insurance systems, platform, and patient & provider product areas. This isn't about project coordination—you're an end-to-end leader of complex technical and critical product-dependent initiatives that are essential to our business success. As the sole TPM for the Insurance platform, you'll have the unique opportunity to establish the TPM function in this space while partnering with engineering leadership to drive our most important technical priorities.

In making mental health more accessible and affordable, we pride ourselves in tackling the largest, most critical problems and opportunities at the company. The TPM brand is a strategic thought partner who simplifies complexity, drives craft and velocity into execution, and raises the bar on operational excellence that scales.

Responsibilities:

Lead critical, high-impact technical programs across Insurance platform including driving key technical initiatives, optimization of systems and processes, and financial remediation initiatives—owning outcomes from discovery through delivery

Drive end-to-end cross-team programs by coordinating cross-functional planning and execution to reduce operational costs and manual workflow inefficiencies

Establish repeatable playbooks, tooling, and systematic improvements for cyclical operational challenges, transforming how we work into predictable, efficient processes

Lead key data rearchitecture initiatives, delivering on a modernization of our data systems, observability, and accelerate decision-making velocity across R&D

Spearhead financial remediation programs across R&D, driving year-over-year improvements

Be a strategic thought partner with Insurance team leadership to balance competing priorities, manage technical dependencies, and align on investment roadmaps

Create scalable frameworks and operating mechanisms that improve operational efficiency, improve insurance operations reliability, and enhance team productivity

Navigate complex stakeholder landscapes across engineering, product, operations, finance, and compliance teams to drive alignment on technical strategy and execution

Communicate program status, risks, and strategic decisions to senior leadership, translating technical complexity into business impact and ROI

You’ll love this role if:

You've driven complex, high-impact programs that span engineering, operations, finance, and compliance—with proven experience owning outcomes end-to-end

You thrive in ambiguous, fast-moving environments where you can structure messy problems, establish clarity, and drive systematic improvements

You're energized by transforming operational chaos into efficient, repeatable processes—turning annual scrambles into smooth, predictable cadences

You're a natural collaborator who builds trust across diverse stakeholders and can influence without authority to get things done

You're a strategic thought partner who can work alongside strong Engineering and Operations leaders to balance technical excellence with business pragmatism

You have executive presence and can communicate complex technical programs to senior leadership, translating initiatives into clear business impact and ROI