Strategy Consultant, Worksite

Job Description

Strategy Consultant, Worksite

Worksite Strategy & Planning

Full-time, Springfield or Boston, MA

The Opportunity

The Worksite Strategy Consultant serves as a strategic and analytic partner to the Worksite business, supporting leadership and frontline teams through consultative execution, data-driven insights, problem-solving, and development of impactful communications. This role is tailored for the unique operating model, growth priorities, and complexity of the Worksite channel. The consultant operates in a highly matrixed environment, acting as a trusted thought partner to senior leaders and the Senior Leadership Team (SLT), translating complex business questions into actionable insights, scalable solutions, and measurable outcomes.

The Team

The Strategy and Planning Team is the heartbeat of the Worksite Channel.  We drive KPI and Executive reporting, readiness, training, financial planning and deployment support to bring accountability to the organization.  We understand and communicate the health of the business to Sr. Leadership as well as our front-line teams.  We are looking to expand on our small organization with someone who shares our passion of working collaboratively and focusing on our partners and customers. 

The Impact

As pace of change continues to accelerate externally and internally, we have greater needs to monitor, understand and communicate the external environment, make deeper use of data/analytics and generate swift insights to inform decision-making.

This role directly supports the company’s strategic pillars by: 

• Synthesizing complex information to create compelling and influential narratives in partnership with leaders from across the organization to ensure strategy and execution are aligned and communicated to executive management

• Independently leading projects and developing solutions to complex strategic business questions that cross disciplines and will advance Worksite goals with clear action items and recommendations.  Uncover the intent of the business questions before answering surface-level questions.

• Delivering actionable insights that improve worksite sales effectiveness, enrollment outcomes, and pipeline visibility through ownership, improvement, and communication of the Worksite Sales Planning tool.

• Operating as a force multiplier by partnering with the Worksite Strategy and Planning team to apply strategic thinking and analysis, automation, and AI to streamline executive report outs, reduce manual effort, improve cycle times, and enable scalable operations. 

The Minimum Qualifications

• Bachelor’s degree

• 5+ years managing complex projects that involve multiple stakeholders in different organizations

• 5+ years’ experience creating simple, powerful and data-driven presentations to senior leaders, specifically PowerPoint and Excel. 

• 2+ years' experience with distribution datasets and building sales planning models

The Ideal Qualifications

• Master’s degree

• 8+ years managing complex projects that involve multiple stakeholders in different organizations

• 8+ years’ experience creating simple, powerful and data-driven presentations to senior leaders, specifically PowerPoint and Excel. 

• 5+ years competitive intelligence and/or corporate strategy experience

• 5+ years' experience in management consulting or strategy with a strong track record of successful delivery

• 5+ years industry experience with life insurance and supplemental health products

• Experience with MekkoGraphics add-on for PowerPoint

• Comfort with ambiguous, ever-changing situations.

• Proven ability to distill down high-quality analysis of large sets of qualitative and quantitative data into simple and actionable key insights tailored to various audiences

• Proven success in a collaborative, team-oriented environment.

• Hypothesis driven problem-solving ability, including skillful translation of business questions into actionable solutions

What You Can Expect at MassMutual
MassMutual offers the opportunity to do meaningful work within a purpose-driven organization that values long-term impact over short-term outcomes. In this role, you can expect:

• Clear areas of ownership and accountability, with work that connects directly to company and customer outcomes

• A collaborative environment where perspectives are welcomed

• Access to learning, development, and internal networks that support continuous growth and skill-building over time

• Employee-led communities and forums that foster connection, learning, and inclusion across the organization

• A culture grounded in integrity, responsibility, and stewardship—supported by a company with a strong legacy and a future-focused mindset

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MassMutual is an equal employment opportunity employer. We welcome all persons to apply.

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