Staff Technical Program Manager

Join Headway's Engineering team as a Staff Technical Program Manager. In this pivotal role, you will define and execute critical technical initiatives, primarily partnering with the Insurance team. You will lead complex, cross-functional programs that impact various aspects of our insurance systems, platform, and patient & provider product areas. As the sole TPM for the Insurance platform, you will establish the TPM function in this space and drive our most important technical priorities. You will also create scalable frameworks and operating mechanisms to improve operational efficiency and enhance team productivity.

• Lead and manage critical technical programs across the Insurance platform, driving key initiatives and owning outcomes from discovery through delivery.
• Establish the TPM function in the Insurance space, creating scalable frameworks and operating mechanisms that improve operational efficiency and enhance team productivity.
• Serve as a strategic thought partner with Insurance team leadership, balancing competing priorities, managing technical dependencies, and aligning on investment roadmaps.
• You're comfortable with high autonomy and can tackle technical and operational challenges across the stack with minimal guidance
• 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've driven complex, high-impact programs that span engineering, operations, finance, and compliance—with proven experience owning outcomes end-to-end
• You have executive presence and can communicate complex technical programs to senior leadership, translating initiatives into clear business impact and ROI
• You're a force multiplier who removes blockers, accelerates decision-making, and enables teams to focus on high-value work
• You're a strategic thought partner who can work alongside strong Engineering and Operations leaders to balance technical excellence with business pragmatism
• You're passionate about operational efficiency and have experience implementing tooling, frameworks, and playbooks that deliver measurable improvements year-over-year
• You're a natural collaborator who builds trust across diverse stakeholders and can influence without authority to get things done
• You care about our mission of building a mental healthcare system that everyone can access