Head of Policyholder Services & Annuity New Business Strategic Planning

The Opportunity 

As Head of Policyholder Services & Annuity New Business (PS&ANB) Strategic Planning, you will play a critical leadership role shaping and executing short- and long-term strategies that support enterprise transformation. As a member of the PS&ANB Senior Leadership Team, you will drive strategic alignment across investments, operating models, and change initiatives while overseeing organizational communications, learning and performance efforts, and financial management. 

You will partner closely with senior leaders and cross-functional stakeholders to assess current capabilities, identify opportunities for improvement, and build sequenced roadmaps that enable sustainable change. This is a highly visible role requiring strong systems thinking, financial acumen, and the ability to influence and guide large organizations through complexity and transformation. 

The Team 

You will join the Policyholder Services & Annuity New Business Senior Leadership Team within Operations. The team is focused on delivering high-quality service outcomes while advancing efficiency, innovation, and transformation across the organization. The culture emphasizes accountability, data-driven decision making, and shared ownership of outcomes through close partnership with Technology, Finance, Legal, Compliance, Audit, and Business stakeholders. 

The Impact 

• Lead enterprise and organizational strategic planning for PS&ANB, ensuring alignment with Operations strategy, investment priorities, and long-term transformation goals. 

• Serve as the business lead for strategic programs and initiatives, including operational deep dives, efficiency efforts, technology enablement, and service strategy development. 

• Own development and ongoing management of the PS&ANB Operating Plan, including prioritization, progress tracking, leader accountability, and resource management. 

• Design and facilitate bi-annual strategy sessions and monthly business reviews using data and defined metrics to assess business health. 

• Partner with senior and executive leaders to influence decision-making and build alignment for complex change initiatives. 

• Oversee business planning and financial operations, including expense management, unit cost stewardship, and efficiency opportunities. 

The Minimum Qualifications 

• Bachelor’s degree required. 

• 10+ years of experience in progressively increasing leadership roles supporting large-scale transformation, M&A, or enterprise initiatives. 

• Significant experience with financial management, expense oversight, and financial reporting. 

• Demonstrated ability to lead complex initiatives and manage competing priorities. 

• Authorization to work in the United States without sponsorship now or in the future. 

The Ideal Qualifications 

• Advanced degree or professional certification (e.g., MBA, FSA, FCIA, CPA). 

• Strong strategic, analytical, and decision-making skills. 

• Proven ability to influence senior and executive leaders across functions. 

• Experience leading organizational change and operating model design. 

• Strong executive presence with excellent written and verbal communication skills. 

• Demonstrated commitment to talent development, inclusion, and continuous improvement. 

What to Expect as Part of MassMutual and the Team 

• Regular meetings with the PS&ANB Senior Leadership Team 

• Focused one-on-one meetings with your manager 

• Broad collaboration with enterprise partners across Operations, Technology, Finance, Legal, Compliance, and Audit 

• Access to learning and development resources to support continued growth 

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