Staff Technical Program Manager

Headway’s mission is to fix this by building a new mental healthcare system everyone can access. 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. 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.

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

Requirements

Driven complex, high-impact programs that span engineering, operations, finance, and compliance—with proven experience owning outcomes end-to-end; Thrive in ambiguous, fast-moving environments where you can structure messy problems, establish clarity, and drive 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 who can work alongside strong Engineering and Operations leaders to balance technical excellence with business pragmatism; Executive presence and can communicate complex technical programs to senior leadership, translating initiatives into clear business impact and ROI; Passionate about operational efficiency and have experience implementing tooling, frameworks, and playbooks that deliver measurable improvements year-over-year; Force multiplier who removes blockers, accelerates decision-making, and enables teams to focus on high-value work; Comfortable with high autonomy and can tackle technical and operational challenges across the stack with minimal guidance; Care about our mission of building a mental healthcare system that everyone can access

Benefits

Equity compensation; Medical, Dental, and Vision coverage; HSA / FSA; 401K; Work-from-Home Stipend; Therapy Reimbursement; 16-week parental leave for eligible employees; Carrot Fertility annual reimbursement and membership; 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st; Flexible PTO; Employee Assistance Program (EAP); Training and professional development