Director, Regulatory Compliance Specialist, Management

Position: Director, Benefits
Ready to help us transform healthcare? Bring your true colors to blue. This role is eligible for our FLEX persona and candidates are expected to be in our Boston or Hingham location on Tuesday and Wednesday each week.

About the Role:

We are seeking a forward-thinking Director, Benefits to redefine and lead our comprehensive benefits and wellbeing strategy. Reporting to the Senior Director, Total Rewards, this pivotal role will drive the evolution of our offerings through continuous innovation, deep market insights, and AI-enabled technology. You will be responsible for the strategic direction, design, and governance of our entire portfolio, encompassing health, welfare, retirement, and holistic wellbeing programs.

This is a unique opportunity for a strategic leader who balances long-term vision with operational excellence, utilizing data analytics to build modern, highly engaging associate experiences.

Your Day to Day Strategic Leadership &

Innovation: Define and execute a multi-year benefits and wellbeing strategy that aligns with our Total Rewards philosophy and broader business objectives. Proactively leverage market insights, data analytics, and AI tools to drive innovation in program design, ensuring our offerings remain highly competitive and meet the evolving needs of our workforce.

Data-Driven Program Design & Management:
Lead the design, implementation, and continuous improvement of all benefit programs with a central focus on associate wellbeing. Utilize data-driven insights to curate physical, mental, and financial wellbeing initiatives that foster a healthy, engaged, and productive workplace culture.

Vendor & Financial Oversight:
Oversee benefits vendor strategy, including selection, contract negotiation, and performance management to maximize service quality, innovation, and value. Manage the benefits budget, conduct annual renewals, and provide financial analysis and recommendations to leadership.

Team Leadership & Cross-Functional Partnership:
Build, mentor, and develop a high-performing benefits team focused on continuous improvement, agility, and operational excellence. Act as a trusted advisor to senior leadership while partnering seamlessly with HR, Finance, Legal, and IT to ensure compliant, efficient program delivery.

Communication & Engagement:
Architect a comprehensive, modernized communication strategy that leverages new technologies and AI to ensure associates understand and appreciate the full value of their benefits. Champion initiatives that drive engagement and utilization, creating a world-class, personalized benefits and wellbeing experience.

This document is not an exhaustive list of all responsibilities, skills, duties, requirements, or working conditions associated with the job. Employees may be required to perform other job-related duties.

We’re Looking for:

Strong financial acumen with demonstrable experience leveraging data analytics, market insights, and AI to drive business decisions, optimize costs, and improve program outcomes.

Proven success designing and managing innovative, competitive benefits and wellbeing programs in a complex organization.

Exceptional communication and negotiation skills, with the executive presence to influence stakeholders at all levels, including the Board of Directors and executive leadership.

Deep expertise in benefits laws and regulations (e.g., ERISA, ACA, HIPAA, COBRA, SECURE Act).Required or desired certifications include Certified Employee Benefit Specialist (CEBS), Certified Benefits Professional (CBP), or similar licensures.

What You Bring:

Bachelor’s degree in Human Resources, Business Administration, or a related field required.
10+ years of progressive experience in benefits administration, wellbeing strategy, and…