Director, Regulatory Compliance Specialist, Management

Overview

The Director of Benefits is a strategic and operational leader responsible for overseeing the design, administration and continuous improvement of the company's health, welfare, retirement, well-being, and leave of absence programs. This role ensures that benefit offers are competitive, cost-effective, compliant, inclusive, and aligned with overall organizational goals. The Director partners closely with HRBPs, Finance, Legal, Payroll, and external partners to deliver a seamless and high-quality employee experience while supporting organizational growth and integration across a multi-entity environment.

• Develop and maintain the company’s benefits strategy, ensuring offerings are competitive, sustainable, and aligned with workforce needs and organizational priorities.
• Lead the full annual benefits planning cycle, including plan design, modeling, budgeting, forecasting, and collaboration with Finance to ensure cost alignment.
• Manage all aspects of annual benefits renewals, including RFPs, vendor evaluations, negotiations, and recommendations balancing competitiveness, cost efficiency, and employee experience.
• Oversee 401(k) and retirement plan governance, including strategy, compliance, plan documents, audits, nondiscrimination testing, Form 5500 filing, and work with recordkeepers, advisors, and fiduciary committees.
• Maintain a comprehensive benefits portfolio that is market-aligned, compliant with state and federal regulations, and inclusive of diverse employee needs.
• Own vendor and partner management, covering medical, dental, vision, disability, life insurance, EAP, wellness programs, COBRA, and other third-party providers. Monitor performance, negotiate service improvements, and ensure high-quality delivery.
• Lead benefit communication and education strategies to support employee understanding, decision-making, and engagement across all programs.
• Ensure compliance with ERISA, ACA, HIPAA, COBRA, FMLA (benefits-related), Section 125, state leave laws, and other relevant regulations. Partner with Legal and consultants to mitigate risk and maintain audit-ready processes.
• Analyze benefits utilization, cost drivers, employee demographics, and participation trends to inform data-driven recommendations for cost containment, experience improvement, and long-term sustainability.
• Drive holistic well-being strategies—including physical, mental, financial, and social—aligned with company culture, engagement goals, and retention objectives.
• Oversee all leave of absence programs, including STD, LTD, FMLA, state leave programs, parental leave, and company leaves.
• Ensure integrated, compliant, and employee-centric LOA processes, working closely with HRBPs, Payroll, managers, and third-party administrators.
• Develop policies, guidelines, and communication approaches that support both compliance and a positive employee experience.
• Monitor LOA trends, escalation patterns, and risk areas; implement process improvements to enhance employee support and operational efficiency.
• Lead and develop the Benefits team, fostering collaboration, technical expertise, continuous improvement, and operational excellence.
• Serve as a trusted advisor to HR leadership, executives, and HRBPs on benefits and leave strategy, design, compliance, and employee communications.
• Collaborate cross-functionally with Legal, Finance, HRIS, Payroll, Communications, and business leaders to ensure cohesive and accurate execution of all benefit and LOA programs.
• Support change management for benefit-related initiatives, ensuring clear communication, adoption readiness, and alignment across business units and acquired entities.

• Minimum of 8 years of progressive experience in employee benefits, retirement plans, or total rewards, with a strong focus on program administration and strategy.
• 3-5+ years of leadership experience managing teams or large vendor ecosystems.
• Deep knowledge of benefits compliance, including ERISA, ACA, COBRA, HIPAA, FMLA, state leave laws, and Section 125 plans.
• Experience in complex, multi-site, or multi-entity organizations; exposure to integration or harmonization efforts preferred.
• Excellent…