Director, Health and Welfare

Sun Life • Hartford, CT

5d • $145,000 - $217,500

About The Position

The Director, Health and Welfare is a strategic program leader responsible for setting the vision and direction and continuously optimizing Sun Life U.S. health and welfare, wellness, and leave of absence programs. The role combines analytical work and strategic planning with hands-on execution, people leadership, and delivery of business results. The Director champions innovation and operational excellence, using best practices and emerging technologies to improve the employee experience and achieve measurable results.

Requirements

• Bachelor’s degree or equivalent work experience.
• 10 or more years of experience managing employee benefits for complex mid-size to large organizations, with a focus on innovative solutions, employee experience, and financial management.
• Proven ability to lead and develop a team.
• Deep expertise in the design, administration, and implementation of health and welfare plans.
• Solid knowledge and understanding of HR programs and their connections.
• Knowledge of leave processes, including short- and long-term disability, FMLA, state leaves, work accommodations, and benefits compliance.
• Strong decision-making and organizational skills.
• Action-oriented approach, with a focus on execution, continuous improvement, employee experience, and operational excellence.
• Excellent interpersonal and communication skills.
• Stakeholder management skills and the ability to build relationships and influence people at all organizational levels, internally and externally.
• Excellent project management and planning skills, including the ability to lead, plan, and organize complex assignments.
• Advanced Microsoft Office skills, particularly Excel and PowerPoint, including the ability to conduct complex analyses and prepare high-quality executive presentations independently.
• Ability to adapt to changing priorities and solve complex problems.
• Ability to work independently and collaboratively in a fast-paced, fluid environment.

Nice To Haves

• Experience with mergers and acquisitions.
• Experience using Microsoft Copilot.

Responsibilities

• Drive the strategic direction of health and welfare, wellness, and leave of absence programs in alignment with business objectives and long-term organizational goals.
• Identify emerging trends and evaluate solutions to recommend program changes that improve employee experience and deliver measurable return on investment.
• Develop analytics, interpret complex data, and provide recommendations to optimize program design, reduce costs, and improve employee outcomes.
• Create executive-ready presentations and business cases explaining complex benefits concepts to leadership and stakeholders.
• Manage vendor partnerships, negotiate contracts, and improve service delivery and cost management.
• Work with senior leaders, finance, and actuarial teams to develop pricing models and contribution strategies that balance employee needs and financial objectives.
• Build and develop a high-performing team through coaching, feedback, knowledge sharing, and development opportunities.
• Identify operational inefficiencies, implement streamlined processes, and use emerging technologies and tools to increase productivity and reduce manual work.
• Collaborate with internal stakeholders and external vendors to promote health and welfare programs and increase engagement.
• Ensure health and welfare plans comply with federal, state, and local regulations, including ERISA, COBRA, and the Patient Protection and Affordable Care Act.
• Partner with the Ireland Business Group by sharing guidance, support, and benefits expertise.
• Lead large-scale projects and change initiatives, including stakeholder engagement, integration, risk management, and operational excellence.
• Monitor industry practices, legislation, and market evaluations to maintain optimized, compliant, and competitive programs.
• Manage benefits program integrations for acquired companies.

Benefits

• Generous vacation and sick time.
• Paid family, parental, and adoption leave.
• Medical coverage.
• Company-paid life and AD&D insurance.
• Disability programs.
• Partially paid sabbatical program.
• 401(k) employer match.
• Stock purchase options.
• Employer-funded retirement account.
• Flexible, inclusive, and collaborative work environment supporting career growth.
• Discretionary annual incentive award based on individual and business performance.

What This Job Offers

• Job Type: Full-time
• Career Level: Director