Director, Health and Welfare

Sun Life•Wellesley, MA

3d•$145,000 - $217,500

About The Position

The Director, Health and Welfare is a strategic program leader responsible for the vision, direction, and continuous optimization of Sun Life U.S.’s health and welfare, wellness, and leave of absence programs. The role combines strategic leadership with hands-on analysis, problem-solving, presentation development, and execution. It calls for strong analytical judgment, people leadership, innovation, and operational excellence to improve employee experience and produce measurable business results. As a member of the Total Benefits Leadership team, the Director aligns benefit programs with business objectives, assesses emerging trends and solutions, develops data-driven recommendations, and oversees vendor relationships, pricing strategies, compliance, and program integrations. The role leads a team and large-scale initiatives, partners with senior leaders and internal and external stakeholders, and supports the Ireland Business Group with benefits expertise. The position requires a bachelor’s degree or equivalent work experience and 10 or more years of experience managing employee benefits for complex mid-size to large organizations. The salary range is $145,000–$217,500, and the position is eligible for a discretionary annual incentive award. Sun Life describes its work environment as flexible, inclusive, and collaborative.

Requirements

Bachelor’s degree or equivalent work experience.
At least 10 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.
Knowledge of HR programs and how they connect.
Knowledge of leave processes, including short-term and long-term disability, FMLA, state leaves, and work accommodations, and of 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 ability to build relationships and influence people at all organizational levels, internally and externally.
Strong project management and planning skills, including the ability to lead, plan, and organize complex assignments.
Advanced Microsoft Office skills, especially Excel and PowerPoint, including the ability to conduct complex analyses and develop executive-ready presentations independently.
Ability to adapt to changing priorities and solve complex problems.
Ability to work independently or 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 and translate complex data into recommendations to optimize plan design, reduce costs, and improve employee outcomes.
Develop presentations and business cases for executive leadership and key stakeholders.
Manage vendor partnerships, negotiate contracts, and improve service delivery and cost management.
Work with senior leadership, finance, and actuarial teams to develop pricing models and contribution strategies.
Build, coach, and develop a high-performing team through feedback, knowledge sharing, and targeted development opportunities.
Identify operational inefficiencies and implement streamlined processes and technologies to improve productivity and reduce manual work.
Collaborate with internal stakeholders and external vendors to promote benefit programs and drive engagement.
Ensure plans comply with federal laws, including ERISA, COBRA, and the Patient Protection and Affordable Care Act, as well as applicable state and local regulations.
Partner with the Ireland Business Group by sharing guidance and benefits subject matter 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 keep programs optimized, compliant, and competitively positioned.
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 that supports career growth.
Discretionary annual incentive award based on individual and business performance.