Senior Technical Program Manager, Insurance Platform

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

Benefits offered by this job

Equity compensation

Medical, Dental, and Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave

Carrot Fertility annual reimbursement

13 paid holidays

Flexible PTO

Employee Assistance Program (EAP)

Training and professional development

Job summary

Headway is seeking a Staff Technical Program Manager to define execution of critical technical initiatives. As the sole TPM for the Insurance platform, you'll lead end-to-end programs spanning engineering, product, operations, finance and compliance, translating complex requirements into clear plans that deliver business impact.

You'll partner with the Insurance team to balance priorities, establish playbooks, and drive improvements in data systems, observability, and automation, helping scale

Qualifications

• End-to-end owner of complex technical and product-dependent initiatives.
• Experience partnering with Engineering, Product, Operations, Finance, and Compliance.
• Strong communication with senior leadership to translate technical complexity into business impact.

Responsibilities

• Lead critical, high-impact technical programs across Insurance platform; drive key initiatives and financial remediation—from discovery through delivery.
• Coordinate cross-functional planning and execution to reduce costs and manual workflow inefficiencies.
• Establish repeatable playbooks, tooling, and systematic improvements for cyclical operational challenges.
• Lead data rearchitecture initiatives, delivering modernization of data systems and observability to accelerate decision-making.
• Spearhead financial remediation programs across R&D, driving year-over-year improvements.
• Be a strategic thought partner with Insurance leadership to balance priorities and align on investment roadmaps.
• Create scalable frameworks and operating mechanisms that improve insurance operations reliability and team productivity.
• Navigate complex stakeholder landscapes to drive alignment on technical strategy and execution.
• Communicate program status, risks, and ROI to senior leadership.

Skills

Program management

Cross-functional leadership

Strategic thinking

Stakeholder management

Data architecture

Operational excellence

Financial remediation

Executive communication

Job description

Headway is seeking a Staff Technical Program Manager to define execution of critical technical initiatives. As the sole TPM for the Insurance platform, you'll lead end-to-end programs spanning engineering, product, operations, finance and compliance, translating complex requirements into clear plans that deliver business impact.

You'll partner with the Insurance team to balance priorities, establish playbooks, and drive improvements in data systems, observability, and automation, helping scale