Senior Benefits Strategy & Compliance Leader

Jobtailor; San Jose (CA); On-site; USD 150,000 - 210,000; Full time

Job summary

Jobtailor is seeking an accomplished benefits leader to shape and manage the U.S. employee benefits strategy. You will oversee health, retirement, wellness, and leave programs, guiding vendor selections, negotiations, and performance while ensuring strict regulatory compliance.

The role requires extensive leadership and deep expertise in budgeting, forecasting, and benefits design. You will partner with HR and business leaders to deliver competitive, cost-effective programs and provide strategic

Qualifications

• 8+ years of progressive employee benefits experience.
• 5+ years of benefits leadership or strategic program ownership.
• Strong knowledge of U.S. benefits regulations and compliance.
• Experience with benefits design, vendor negotiations, budgeting, and forecasting.
• Strong leadership, communication, analytical, and presentation skills.

Responsibilities

• Develop and manage the company’s U.S. benefits strategy and programs.
• Oversee health and welfare, retirement, wellness, and leave programs.
• Lead vendor selection, contract negotiations, renewals, and performance.
• Manage benefits budgets, forecasting, utilization, and cost analysis.
• Ensure compliance with ERISA, ACA, COBRA, HIPAA, FMLA, Section 125, and other applicable regulations.
• Monitor legislative changes and recommend program updates.
• Lead open enrollment, employee communications, and benefits education.
• Develop benefits metrics, dashboards, and executive reporting.
• Benchmark programs and recommend improvements to competitiveness and employee value.
• Lead and develop benefits team members, as applicable.
• Partner with HR and business leaders to deliver competitive, cost-effective, and compliant programs

Skills

Leadership

Communication

Analytical skills

Presentation skills

Benefits design

Budgeting & forecasting

Education

CEBS Certification

Tools

ADP

SAP SuccessFactors

FMLASource

Job description

Jobtailor is seeking an accomplished benefits leader to shape and manage the U.S. employee benefits strategy. You will oversee health, retirement, wellness, and leave programs, guiding vendor selections, negotiations, and performance while ensuring strict regulatory compliance.

The role requires extensive leadership and deep expertise in budgeting, forecasting, and benefits design. You will partner with HR and business leaders to deliver competitive, cost-effective programs and provide strategic