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
#LI-JF1
MassMutual is an equal employment opportunity employer. We welcome all persons to apply.
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
California residents: For detailed information about your rights under the California Consumer Privacy Act (CCPA), please visit our California Consumer Privacy Act Disclosures page.
Salary Range: $128,000-$168,000
Skills Required
- Bachelor's degree
- 5+ years managing complex projects involving multiple stakeholders
- 5+ years creating data-driven presentations to senior leaders using PowerPoint and Excel
- 2+ years experience with distribution datasets and building sales planning models
- Master's degree
- 8+ years managing complex projects involving multiple stakeholders
- 8+ years creating data-driven presentations to senior leaders using PowerPoint and Excel
- 5+ years competitive intelligence and/or corporate strategy experience
- 5+ years experience in management consulting or strategy with successful delivery
- 5+ years industry experience with life insurance and supplemental health products
- Experience with MekkoGraphics add-on for PowerPoint
- Proven ability to distill large qualitative and quantitative data into actionable insights
- Comfort with ambiguous, ever-changing situations and hypothesis-driven problem solving
MassMutual Compensation & Benefits Highlights
How does MassMutual ensure its pay and bonus plans are competitive?
MassMutual supports competitive compensation through salary and bonus opportunities, retirement contributions, pay transparency practices and a broad benefits package that adds value beyond base pay. The company also uses long-running pay equity reviews and employee feedback to evaluate whether rewards are supporting employees across roles and life stages.
- Competitive pay and bonus opportunities: MassMutual describes its total rewards approach as holistic and flexible, with competitive salaries and bonuses designed to support employees’ financial well-being. Employees also point to compensation as part of the value proposition, with one sales assistant citing “great benefits and lots of flexibility,” and another employee describing the company’s “good leadership and benefits.”
- Retirement and financial benefits: MassMutual provides a 401(k) benefit of up to 10% of eligible compensation, including a 5% company match and a 5% annual company contribution. The company also treats eligible student loan payments like 401(k) contributions for matching purposes and begins monthly retirement healthcare account contributions for employees starting at age 45.
- Pay transparency and pay equity: MassMutual posts salary ranges in most job postings and has used an independent HR risk management firm to conduct annual adjusted pay gap reviews for 17 years. That approach connects compensation competitiveness with equity and accountability across the employee experience.
- Benefits as part of total rewards: MassMutual’s compensation includes health, dental and mental health benefits, caregiver leave, parental leave, bereavement leave, paid volunteer time, flexible holidays and a Well-Being Wallet of up to $1,250 annually. A head of human resources said, “It’s not about industry standards — it’s about supporting all employees’ well-being in ways that are meaningful to them.”
- External signals:
- Benefits value: Employees on external review sites regularly highlight benefits as a strength, with reviews calling out “excellent benefits,” “great benefits” and a “great benefits package.” (Glassdoor; Indeed)
- Compensation and retention: Employees surveyed on external review sites rate MassMutual’s perks and benefits an A-, with 100% saying perks and benefits play a role in staying at the company. (Comparably)
- Financial stability: MassMutual reported more than $10 billion in insurance and annuity benefits paid in 2025 and total adjusted capital above $34 billion, reinforcing the company’s long-term financial foundation. (MassMutual 2025 Annual Report)
Bottom line: MassMutual supports competitive pay through salary and bonus opportunities, strong retirement contributions, pay transparency, recurring pay equity reviews and benefits designed to support employees’ financial, physical, mental and family well-being.
MassMutual Insights
What We Do
Since 1851, MassMutual’s commitment has always been to help people protect their families, support their communities, and help one another. This is why we want to inspire people to Live Mutual. We’re people helping people. Together, we’re stronger.
Why Work With Us
MassMutual has the financial security and stability of a 170+ year old company, with the culture and energy of a startup. We work every day with the customer front of mind to build the best digital experience in the industry.
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Employees engage in a combination of remote and on-site work.
We believe in capitalizing on the best of being together in our offices as well as personal flexibility. Our workplace philosophy puts office collaboration first, combined with flexibility to work remotely.



