Director, Health & Welfare

Sun Life

Director managing strategic health and welfare programs for Sun Life, with a focus on innovation and employee experience. Leading a high-performing team and ensuring program compliance.

Posted 5/13/2026full-timeWellesley Hills • Connecticut, Maine, Massachusetts • 🇺🇸 United StatesLead💰 $145,000 - $217,500 per yearWebsite

About the role

Key responsibilities & impact

Drive the strategic direction of Sun Life’s health and welfare, wellness and leave of absence programs
Drive innovation in health, welfare, wellness and leave of absence programs
Lead data-driven decision-making by developing meaningful analytics
Independently develop high-quality presentations and business cases
Cultivate and manage partnerships with key vendors
Collaborate with senior leadership to develop pricing models and contribution strategies
Build and cultivate a high performing team
Champion continuous improvement and process optimization
Ensure health and welfare plans are compliant with all federal laws and state regulations
Manage program integrations of acquired companies

Requirements

What you’ll need

Bachelor’s Degree or equivalent work experience
10+ years of experience managing employee benefits for complex mid-size to large organizations
Proven ability to effectively lead and develop a team
Deep expertise and experience in the design, administration and implementation of health and welfare plans
Experience with mergers and acquisitions a plus
Solid knowledge and understanding of HR programs and connections
Knowledge of leave processes (short-term and long-term disability, FMLA, state leaves, work accommodations) and benefits compliance
Strong decision-making and organizational skills
Excellent interpersonal/communications skills
Skilled in stakeholder management
Excellent project management and planning skills
Excellent excel and analytical skills with ability to summarize results in understandable format with insights

Benefits

Comp & perks

Generous vacation and sick time
Market-leading 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

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

data analyticspresentation developmentbusiness case developmentpricing modelshealth and welfare plan designhealth and welfare plan administrationhealth and welfare plan implementationbenefits complianceleave processesproject management

Soft Skills

leadershipteam developmentdecision-makingorganizational skillsinterpersonal skillscommunication skillsstakeholder managementcollaborationcontinuous improvementprocess optimization

Certifications

Bachelor’s Degree