Staff Technical Program Manager — Insurance Platform

Headway; United States; Remote; USD 190,000 - 238,000; Full time

Benefits offered by this job

Equity compensation

Medical, Dental, and Vision coverage

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave

Carrot Fertility annual reimbursement

Flexible PTO

Employee Assistance Program (EAP)

Training and professional development

Job summary

Headway is building a new mental healthcare system accessible to all. As Staff Technical Program Manager you will define execution plans for critical Insurance-aligned initiatives, partnering with engineering, product, operations, and finance to deliver measurable business impact.

You’ll own end-to-end programs, establish repeatable playbooks, drive data architecture improvements, and coordinate with leadership to align roadmaps and budgets while maintaining a strong focus on delivery velocity

Qualifications

• Experience owning outcomes end-to-end across multi-team programs.
• Ability to structure messy problems and establish clarity for execution.
• Proven track record delivering cross-functional initiatives with ROI.

Responsibilities

• Lead critical, high-impact technical programs across Insurance platform with end-to-end ownership.
• Coordinate cross-functional planning to reduce costs and manual workflows.
• Establish repeatable playbooks, tooling, and improvements for operational challenges.
• Drive data rearchitecture and modernization of data systems and observability.
• Spearhead financial remediation programs and align with leadership roadmaps.
• Balance priorities with Insurance leadership and manage dependencies.
• Create scalable operating frameworks to improve reliability and productivity.
• Navigate stakeholder landscapes and translate status to senior leadership.

Skills

End-to-end ownership

Cross-functional planning

Stakeholder management

Strategic execution

Communication to leadership

Operational excellence

Program governance

Problem structure & analysis

Influence without authority

Tools

Data architecture

PM tooling & playbooks

Job description

Headway is building a new mental healthcare system accessible to all. As Staff Technical Program Manager you will define execution plans for critical Insurance-aligned initiatives, partnering with engineering, product, operations, and finance to deliver measurable business impact.

You’ll own end-to-end programs, establish repeatable playbooks, drive data architecture improvements, and coordinate with leadership to align roadmaps and budgets while maintaining a strong focus on delivery velocity