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HeadwayHeadway

Staff Technical Program Manager

Lead high-impact technical programs for the Insurance platform as the sole TPM, driving cross-functional execution, data rearchitecture, and operational improvements that deliver business-critical outcomes.

About the job

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

  • Proven experience driving complex, high-impact programs that span engineering, operations, finance, and compliance—owning outcomes end-to-end
  • Experience thriving in ambiguous, fast-moving environments where you can structure messy problems, establish clarity, and drive systematic improvements
  • Experience transforming operational chaos into efficient, repeatable processes—turning annual scrambles into smooth, predictable cadences
  • Strong collaboration skills with ability to build trust across diverse stakeholders and influence without authority
  • Experience working alongside strong Engineering and Operations leaders to balance technical excellence with business pragmatism
  • Executive presence with ability to communicate complex technical programs to senior leadership, translating initiatives into clear business impact and ROI
  • Experience implementing tooling, frameworks, and playbooks that deliver measurable improvements year-over-year
  • Comfort with high autonomy and ability to tackle technical and operational challenges across the stack with minimal guidance

Nice-to-Haves

  • Passion for operational efficiency and building scalable frameworks

Skills

Technical Program Management, Cross-Functional Program Management, Stakeholder Management, Data Architecture, Process Improvement, Operational Efficiency, Risk Management, Executive Communication, Project Planning, Dependency Management

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