# Staff Technical Program Manager
**Company:** [Headway](https://hotfix.jobs/companies/headway)
**Location:** Remote
**Salary:** $190K-$238K
**Experience:** 7+ years
**Skills:** Technical Program Management, Cross-Functional Program Management, Stakeholder Management, Data Architecture, Process Improvement, Operational Efficiency, Risk Management, Executive Communication, Project Planning, Dependency Management
**Posted:** 2026-06-25
> 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.
## Job Description
## 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
**Apply:** https://hotfix.jobs/jobs/staff-technical-program-manager-at-headway-2995bea9-af6d-4380-ab8f-c10516a33c33
**Canonical:** https://hotfix.jobs/jobs/staff-technical-program-manager-at-headway-2995bea9-af6d-4380-ab8f-c10516a33c33