Technical Program Manager

Overview

Join to apply for the Staff Technical Program Manager role at Headway
. Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software‑enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z, Accel, GV, Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

• 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 with a strategic thought partner approach, transforming complex cross‑functional challenges into clear execution plans that drive top‑line business impact on our most critical company OKRs.
• Primarily partner with the Insurance team to lead key programs that touch nearly every aspect of our insurance systems, platform, and patient & provider product areas. As the sole TPM for the Insurance platform, you’ll establish the TPM function in this space and partner with engineering leadership to drive our most important technical priorities.
• Lead critical, high‑impact technical programs across the 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 data re-architecture initiatives, delivering on a modernization of our data systems, observability, and accelerated 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, balancing competing priorities, managing technical dependencies, and aligning on investment roadmaps.
• Create scalable frameworks and operating mechanisms that improve operational efficiency, enhance insurance operations reliability, and boost 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.

• Has driven complex, high‑impact programs that span engineering, operations, finance, and compliance with proven experience owning outcomes end‑to‑end.
• Thrives in ambiguous, fast‑moving environments, structuring messy problems, establishing clarity, and driving systematic improvements.
• Energized by transforming operational chaos into efficient, repeatable processes—turning annual scrambles into smooth, predictable cadences.
• Natural collaborator who builds trust across diverse stakeholders and can influence without authority to get things done.
• Strategic thought partner capable of working alongside strong Engineering and Operations leaders to balance technical excellence with business pragmatism.
• Executive presence with the ability to communicate complex technical programs to senior leadership, translating…