Director of Benefits

Position Summary:

Our client, a global, multi-site retail and consumer services organization, is seeking a Benefits Director to lead the day-to-day operations of their employee benefits function. This role reports directly to the VP of Total Rewards and is based on-site at the company’s office in the greater Boston area.

This is a high-impact leadership role focused on overseeing the administration, compliance, and continuous improvement of benefits programs across a large, multi-state workforce, supporting both retail and corporate populations.

Absolute Minimum Must-Have’s / Experience / Requirements:

• Bachelor’s degree required (HR, Business, or related field)
• 5–7 years of progressive experience in benefits administration or total rewards
• Strong knowledge of benefits regulations including ERISA, HIPAA, ACA, and COBRA
• Comprehensive experience with health & welfare and retirement plan administration
• Experience with leave of absence programs
• Experience managing a team and direct reports
• Vendor management experience (brokers, TPAs, and related partners)
• Advanced Excel skills (pivot tables, lookups, data analysis)
• Experience administering benefits across a multi-state workforce
• Experience managing open enrollment for a large, distributed employee population
• Strong analytical and problem-solving capabilities with ability to diagnose issues and implement solutions
• Ability to translate complex benefits data into actionable insights and recommendations
• Strong understanding of internal controls, risk management, and benefits governance
• Demonstrated ability to manage multiple priorities in a fast-paced, high-volume environment
• High level of discretion, confidentiality, and sound judgment
• Strong program and process management skills

Key Responsibilities:

What You’ll Do

• Oversee administration of all health, welfare, and retirement benefit programs, ensuring accuracy, efficiency, and strong internal controls
• Partner with HRIS, Payroll, and Finance to ensure seamless benefits operations including enrollment, billing, and data integrity
• Lead end-to-end open enrollment strategy and execution, including communications and employee education across corporate and field populations
• Manage vendor relationships including brokers, third-party administrators, and other partners, ensuring accountability and service delivery
• Ensure full compliance with all federal, state, and local regulations and maintain all required plan documentation and communications
• Analyze benefits utilization, market trends, and cost data to support plan renewals and program effectiveness
• Support ongoing efforts to enhance the competitiveness and cost-effectiveness of benefit offerings
• Serve as escalation point for complex benefits issues, ensuring a strong employee experience
• Lead, develop, and coach the benefits team, fostering a high-performing and service-oriented culture
• Partner cross-functionally to improve data quality, reporting, and system capabilities

Key Desired Business Outcomes

What Success Looks Like

First 6 Months:

• Build strong relationships with Total Rewards, HR, Finance, Payroll, and key vendor partners
• Assess current benefits programs, processes, and systems to identify gaps and improvement opportunities
• Gain full understanding of existing plans, costs, and employee utilization
• Identify and address any immediate compliance or operational risks
• Establish clear priorities, workflows, and expectations for the benefits team
• Begin planning for the upcoming open enrollment cycle

First 12 Months:

• Successfully execute a full open enrollment cycle across a large, distributed workforce
• Support improvements to benefits programs to enhance competitiveness and cost efficiency
• Establish reliable benefits data, reporting, and operational processes
• Ensure full compliance with all regulatory requirements
• Build a high-performing, process-driven benefits team with strong vendor management
• Be recognized as a trusted resource for benefits across the organization