✦ Luna Orbit — Project & Program Management

Head of AI Strategy

at Massachusetts Mutual Life Insurance

📍 Boston, MA Onsite 💰 $189K – $249K USD / year Posted March 29, 2026
Salary $189K – $249K USD / year
Type Full-Time
Experience lead
Exp. Years 4+ years (consulting) or 10+ years (financial services)
Education Bachelor's Degree from leading college or university
Category Project & Program Management

Head of AI Strategy leads the Strategy & Partnerships team within R&D to drive enterprise-wide AI initiatives and transformation. The role partners with executives to define transformation approaches and deliver measurable AI outcomes at scale.

  • Define transformation approach for AI initiatives
  • Lead AI Strategy Associate team and board-ready deliverables
  • Solve ambiguous problems with quantitative/qualitative analyses
  • Create data-driven communications to influence senior leaders
  • Partner on change management and impact tracking

Focus on AI strategy, generative/agentic AI, data/financial analysis, and executive storytelling to influence leadership decisions and board-level updates; experience with agile and cross-functional collaboration.

The ideal candidate is an experienced strategy leader with a background in AI/technology strategy and a track record of leading transformation programs in financial services, capable of engaging executive stakeholders and guiding cross-functional teams.

4+ years of experience at a top-tier strategy consulting firm OR 10+ years in financial services strategy transformationBachelor's Degree from leading college or universityExperience leading substantive portions of project teams OR substantial people leadership experienceAbility to break down problems structurally and synthesize insights
Bachelor's degree in Investment/Business or an analytical field (EconomicsMathematicsEngineeringor CS)Experience in life insurance or broader financial servicesExperience with emerging technologies such as AIquantum computingblockchainExperience in an agile work environmentStrong organizational skills and detail orientationOutcome-oriented with big-picture vs. detail orientation balanceClear objective/plan/status/results communicationLeadership without authority
Board communicationsExecutive presentation toolsFinancial analysis toolsStrategic planning frameworks
strategy consultingprogram leadershipAI strategygenerative AIagentic AIdata analysisfinancial analysisboard updatesexecutive leadership communicationcross-functional collaborationchange managementagileleadershipTransformational leadershipMassMutualStrategy & Partnerships
strategy consultingprogram leadershipAI strategygenerative AIagentic AIdata analysisfinancial analysisboard of directors updatesexecutive leadership communicationcross-functional collaborationchange managementagileleadershipteam leadershipTransformational leadershipMassMutualStrategy & PartnershipsR&Dcommunication
strong communicationexecutive presenceproblem solvingcreative storytellinginfluencing without authorityadaptabilityteam collaboration
Industry Insurance
Job Function Lead the enterprise AI strategy and transformation efforts across MassMutual’s Strategy & Partnerships team
Role Subtype Program Manager
Tech Domains Artificial Intelligence, Data Analysis, Financial Analysis, Strategy & Transformation, Enterprise Technology Experience, R&D
head of ai strategyai strategystrategy and partnershipsenterprise technology experiencer&dstrategy consultingprogram leadershipdata analysisfinancial analysisboard updatesexecutive leadershipcross-functionalchange managementagileteam leadershipmassmutualbpinsstrategy & partnershipsexecutive communication
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