Director, AI-Driven Benefits & Wellbeing

Blue Cross and Blue Shield of Massachusetts Inc.; Boston (MA); Hybrid; USD 189,000 - 231,000; Full time

Benefits offered by this job

Paid time off

Medical/dental/vision insurance

401(k) with match

Well-being benefits

Job summary

Blue Cross Blue Shield of Massachusetts is seeking a Director of Benefits in Boston to define and lead a multi-year benefits and wellbeing strategy. You will drive innovation using data analytics and AI, shaping health, welfare, retirement, and holistic wellbeing programs for a large workforce.

You will collaborate with senior leadership, manage vendor relations and budgets, and mentor a high-performing team to deliver a world-class benefits experience.

Qualifications

• Bachelor’s degree in Human Resources, Business Administration, or related field.
• 10+ years of progressive experience in benefits administration, wellbeing strategy, and Total Rewards with at least 5 years in a leadership role.
• Strong communication and negotiation skills with executive presence to influence stakeholders.
• Deep expertise in benefits laws and regulations (ERISA, ACA, HIPAA, COBRA, SECURE Act).
• Certifications such as CEBS or CBP or similar licensure preferred.

Responsibilities

• Define and execute a multi-year benefits and wellbeing strategy aligned to Total Rewards philosophy.
• Lead design, implementation, and improvement of benefit programs focused on associate wellbeing.
• Oversee benefits vendor strategy, including selection, contracts, performance, and budget.
• Build and mentor a high-performing benefits team and partner with HR, Finance, Legal, and IT.
• Architect a modernized communication strategy leveraging AI to drive engagement and understanding of benefits.

Skills

Financial acumen

Data analytics

AI tools

Executive presence

Education

Bachelor's degree in Human Resources or Business Administration

Job description

Blue Cross Blue Shield of Massachusetts is seeking a Director of Benefits in Boston to define and lead a multi-year benefits and wellbeing strategy. You will drive innovation using data analytics and AI, shaping health, welfare, retirement, and holistic wellbeing programs for a large workforce.

You will collaborate with senior leadership, manage vendor relations and budgets, and mentor a high-performing team to deliver a world-class benefits experience.