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 skillsKey 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 capabilitiesKey Desired Business OutcomesWhat Success Looks LikeFirst 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 cycleFirst 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

Created: 2026-05-09