Director of Benefits

Great Day Improvements - Director of Benefits Director

As the Director of Benefits, you will be responsible for leading the strategy, design, execution, and performance of the organization’s benefits programs, including health and welfare, retirement, leave, and workers’ compensation. This role operates as the senior subject matter authority for benefits and serves as a strategic partner to the Sr. Director of Total Rewards & People Operations in shaping enterprise rewards strategy.

The Director of Benefits ensures programs are competitive, compliant, financially sustainable, and scalable to support organizational growth. This role leads the benefits function and collaborates cross-functionally to align programs with workforce strategy, business priorities, and total rewards philosophy.

Strategic Leadership & Program Ownership

• Partner directly with the Sr. Director of Total Rewards & People Operations to establish and execute the organization’s benefits philosophy, long-term strategy, and multi-year roadmap.
• Lead the design, evaluation, and evolution of all benefits programs including medical, dental, vision, life, disability, retirement, wellness, leave of absence, and workers’ compensation.
• Ensure benefits programs support workforce strategy, organizational growth, talent attraction, retention, and cost sustainability objectives.
• Evaluate market trends, benchmarking data, regulatory developments, and competitive intelligence to inform strategic decisions.
• Recommend plan design changes, funding strategies, and program enhancements based on financial analysis and workforce insights.

Financial Oversight & Cost Strategy

• Own benefits financial strategy including forecasting, budgeting, trend analysis, and long-range cost modeling.
• Analyze claims data, utilization patterns, risk exposure, and cost drivers to identify opportunities for cost containment and program optimization.
• Develop financial models to evaluate vendor proposals, renewal options, and plan design scenarios.
• Present recommendations and strategic insights to leadership.

Governance, Compliance & Risk Management

• Ensure enterprise compliance with all federal, state, and local benefits regulations including ERISA, ACA, COBRA, HIPAA, FMLA, ADA, IRS, and DOL requirements.
• Oversee all regulatory filings, audits, nondiscrimination testing, and reporting obligations.
• Establish internal controls and governance standards to maintain compliance and fiduciary responsibility.
• Identify compliance risks and implement mitigation strategies.

Vendor Strategy & Performance Management

• Lead vendor strategy with Sr. Director of Total Rewards & People Operations including selection, contract negotiation, implementation, and performance oversight.
• Evaluate vendor performance, pricing, service delivery, and contract terms to ensure value and alignment with organizational objectives.
• Direct broker relationships and renewal negotiations.

Operational Leadership & Infrastructure Development

• Provide oversight of benefits administration operations to ensure accuracy, efficiency, and service excellence.
• Establish scalable processes, systems, and workflows to support organizational growth.
• Ensure data integrity across HRIS, payroll, and vendor platforms.
• Oversee implementation of new benefits programs, system integrations, and process improvements.

Team Leadership & Capability Building

• Lead, develop, and mentor the benefits team, including setting priorities, performance expectations, and development plans.
• Build organizational capability through process design, documentation, training, and operational standards.
• Foster a culture of accountability, service excellence, and continuous improvement.

Analytics, Reporting & Executive Communication

• Oversee development of reporting and analytics related to utilization, participation, cost trends, and program performance.
• Translate complex data into actionable insights for leadership.
• Present strategic recommendations, risks, and opportunities to senior leadership and cross-functional partners.
• Ensure leadership receives clear, accurate, and timely benefits intelligence to support business planning.

Cross-Functional Partnership

• Collaborate with Finance, Legal, Payroll, HRIS, and Operations to align benefits with business priorities.
• Support enterprise workforce planning and financial forecasting through benefits cost projections.
• Serve as the organization’s primary internal authority on benefits strategy, policy, and compliance.

• Bachelor's degree in HR, Business Administration, Finance, or related field; Master’s degree or CEBS/SPHR/SHRM-SCP preferred.
• 10+ years of progressive experience in benefits administration and strategy, with hands-on experience in both compliance and systems.
• Experience in self-insured environments, benefits cost modeling, and program design.
• Proven ability to analyze, forecast, and communicate benefits trends, risks, and opportunities with financial acumen.
• Demonstrated leadership experience, including team development and vendor performance management.

Skills and Attributes:

• Detail-oriented and data-driven, with strong analytical, reporting, and problem-solving skills.
• Effective communicator and educator across all levels of the organization.
• High level of comfort with benefits systems, data audits, and technology (ADP and other HRIS platforms a plus).
• Agile learner with a collaborative mindset, able to work in a high-growth, change-oriented environment.
• Passionate about improving employee experience and total rewards impact while managing cost-effectiveness.

GDI is an Equal Employment Opportunity Employer

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