Director of Benefits
McLean, VA | Hybrid | Full-Time | $166,000 – $248,000
Financial Services
We are seeking a
Director of Benefits
to lead the strategy, design, and execution of a comprehensive, enterprise-wide benefits program within a large, complex organization.
This is a senior leadership role responsible for shaping a
competitive, cost-effective benefits strategy
while ensuring operational excellence, compliance, and a strong employee experience.
Position Overview
The Director of Benefits will define and execute the organization’s benefits strategy, overseeing plan design, vendor partnerships, compliance, and administration. This role partners closely with senior HR leadership and executive stakeholders to align benefits programs with broader business and talent objectives.
The ideal candidate brings deep expertise in
benefits strategy, large-scale program management, and team leadership
, along with the ability to balance strategic vision and operational execution.
Key Responsibilities
Benefits Strategy & Design
• Develop and execute a long-term benefits strategy aligned with business and talent priorities
• Evaluate workforce data, utilization trends, and market benchmarks to inform plan design
• Recommend benefit investments and enhancements to senior leadership
Vendor Strategy & Management
• Lead vendor selection and partnership strategy across medical, retirement, and ancillary benefits
• Negotiate contracts and manage vendor performance to optimize cost and service delivery
• Drive innovation through strategic vendor relationships
Operational Excellence
• Oversee benefits administration and ensure seamless delivery across the organization
• Manage benefits budget, forecasting, and financial performance
• Lead annual enrollment strategy and execution with high employee engagement
Compliance & Governance
• Ensure compliance with all applicable regulations including ERISA, ACA, COBRA, and HIPAA
• Maintain governance frameworks to support consistent and compliant plan administration
• Mitigate risk through proactive oversight and internal controls
Leadership & Stakeholder Engagement
• Lead and develop a high-performing benefits team
• Serve as a trusted advisor to senior leadership (CHRO, CFO, executive team)
• Drive cross-functional collaboration across HR, Finance, and external partners
• Represent the organization in industry forums and thought leadership initiatives
Requirements
Required Qualifications
• Bachelor’s degree in Human Resources, Business, or related field
• 15+ years of experience in employee benefits
• 7–10+ years of experience leading benefits strategy, design, and administration in large organizations
• Proven experience managing vendor selection, contract negotiation, and performance
• Strong leadership experience with the ability to build and develop high-performing teams
• Deep knowledge of benefits regulations (ERISA, ACA, COBRA, HIPAA)
• Strong analytical and financial management skills
• Excellent executive-level communication and influencing skills
Preferred Qualifications
• CEBS or similar professional certification
• Experience with self-insured health plans and claims analytics
• Experience supporting retiree medical and actuarial valuation processes
• Experience in large, complex, enterprise environments (5,000+ employees)
