Director, Benefits

Blue Cross Blue Shield of Massachusetts•Boston, MA

2d•$189,360 - $231,440•Hybrid

About The Position

Blue Cross Blue Shield of Massachusetts is seeking a forward-thinking Director, Benefits to define and lead its comprehensive benefits and wellbeing strategy. Reporting to the Senior Director, Total Rewards, the role will shape the strategic direction, design, and governance of health, welfare, retirement, and holistic wellbeing programs. The director will use market insights, data analytics, and AI-enabled technology to innovate, remain competitive, and create engaging associate experiences. The role combines long-term strategic planning with operational and financial oversight. It includes managing vendors and budgets, leading a high-performing benefits team, advising senior leaders, partnering across HR, Finance, Legal, and IT, and developing communications that help associates understand and use their benefits. The position is eligible for the FLEX persona, with expected attendance at the Boston or Hingham location on Tuesdays and Wednesdays each week.

Requirements

Bachelor’s degree in Human Resources, Business Administration, or a related field.
At least 10 years of progressive experience in benefits administration, wellbeing strategy, and Total Rewards.
At least 5 years in a significant leadership role.
Strong financial acumen and demonstrable experience using data analytics, market insights, and AI to inform decisions, optimize costs, and improve outcomes.
Proven success designing and managing innovative, competitive benefits and wellbeing programs in a complex organization.
Exceptional communication and negotiation skills, with executive presence to influence stakeholders at all levels, including the Board of Directors and executive leadership.
Deep expertise in benefits laws and regulations, including ERISA, ACA, HIPAA, COBRA, and the SECURE Act.

Nice To Haves

Certified Employee Benefit Specialist (CEBS), Certified Benefits Professional (CBP), or similar licensure.

Responsibilities

Define and execute a multi-year benefits and wellbeing strategy aligned with the Total Rewards philosophy and business objectives.
Use market insights, data analytics, and AI tools to innovate program design and respond to workforce needs.
Lead the design, implementation, and continuous improvement of benefit programs, including physical, mental, and financial wellbeing initiatives.
Oversee benefits vendor selection, contract negotiations, 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.
Build, mentor, and develop a high-performing benefits team focused on continuous improvement, agility, and operational excellence.
Advise senior leadership and partner with HR, Finance, Legal, and IT on compliant and efficient program delivery.
Develop a modern benefits communication strategy using new technologies and AI to improve associate understanding, engagement, and utilization.