Mutual Opportunities
Director, Worksite Re-Enrollment
Springfield, Massachusetts; Boston, Massachusetts
Thank you to our employees for voting us one of the top places to work in Massachusetts for seven consecutive years!
Overview
A career with us means you’ll work alongside exceptional people and be empowered to reach your professional and personal goals. Our employees are at the foundation of what enables MassMutual to deliver on our purpose to help people secure their futures and protect the ones they love.
We embrace the idea that we all are stronger and better through our support for one another. We strive to create a culture where employees feel valued and are celebrated for who they are.
“Since our founding in 1851, mutuality has put our policyowners at the center of everything we do. At our core, we’re a company of people helping people in their time of need, and that spirit extends to the culture we’ve built at our company. Our employees support and rely on each other each day, collaborating to deliver the best solutions for our customers and help millions more secure their future and protect the ones they love.”
Job Description
Director, Worksite Re-Enrollment
Worksite
Springfield or Boston
The Opportunity
As the Director, Worksite Re-Enrollment you will lead a high-performing team focused on retaining and growing revenue across existing employer groups through effective renewals and re-enrollment strategies. You will play a critical role in driving participation, increasing product adoption, and delivering a best-in-class customer experience that strengthens relationships with producers, brokers, and clients.
In this role, you will operate as a strategic leader and trusted advisor—shaping renewal strategy, elevating enrollment execution, and influencing cross-functional partners including Sales, Service, Implementation, Underwriting, and Operations. You will own outcomes related to retention, revenue growth, and customer experience, ensuring your team delivers consistent, high-quality results
The Team
You will lead a team responsible for renewal execution, re-enrollment strategy, and revenue growth across a defined book of business. The team operates at the intersection of Sales, Service, and Operations, partnering closely with internal stakeholders to deliver seamless enrollment experiences.
This group is focused on building strong external relationships with producers, brokers, and clients while continuously improving processes, outcomes, and customer satisfaction. The culture emphasizes accountability, collaboration, and continuous improvement through data-driven decision making and coaching.
The Impact
Develop and maintain the overall re-enrollment strategy, roadmap, and timelines across all opportunities.
Lead, coach, and develop a high-performing team responsible for renewal execution, re-enrollment strategy, and revenue growth across the assigned book of business.
Set clear performance expectations aligned to retention, participation, revenue, and customer experience outcomes; translate goals into weekly priorities and individual accountabilities.
Use data and observation to identify performance gaps; create targeted development plans and provide timely feedback, recognition, and course correction.
Maintain and grow relationships with top-performing producers to support ongoing engagement and production.
Develop and maintain process documentation, KPIs, metrics and report out to all levels of the organization.
Collaborate with sales, service, and internal business teams to drive enrollment adoption.
Conduct root-cause analysis when issues arise; lead corrective actions and implement controls to prevent recurrence.
Stay abreast of industry best practices, competitive intelligence, and emerging trends to drive customer experience enhancements.
The Minimum Qualifications
7+ years of experience in workplace/group benefits, including sales, account management, renewals, and/or customer-facing roles
3+ years of experience delivering measurable revenue results, including retention, participation growth, and customer experience, with accountability for business performance in a sales or revenue-generating environment
Ability to travel up to 15% of the time
The Ideal Qualifications
Proven experience leading and developing teams, including performance management, coaching, and talent development
Experience with voluntary insurance products (preferred): group whole life, accident, critical illness, hospital indemnity, and long-term care.
Experience leading renewals and re-enrollment efforts for employer groups, including campaign planning and stakeholder coordination
Strong consultative selling and influencing skills with the ability to engage senior employer contacts and producers/brokers
Experience with voluntary insurance products such as group whole life, accident, critical illness, hospital indemnity, or long-term care
Demonstrated ability to manage multiple concurrent priorities and drive cross-functional execution
Data-driven approach to leadership, including use of dashboards, participation analytics, and performance metrics
Bachelor’s degree
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-focusedmindset
#LI-RS1
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.
MassMutual will accept applications on an ongoing basis until such time as a candidate has been offered employment. The job description includes the main duties of this position, which may evolve over time. You may be required to perform other duties not listed.
It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment.
Salary Range: $121,800-$159,800
Hiring Process
Explore
Explore our open jobs by clicking 'search jobs' to find a position that aligns with your experience and skills. You may also consider joining our Talent Network.
Apply
Click the “apply” button on that job posting to complete and submit your application. Your application will be reviewed by a recruiter, which, due to the volume of applications received, may take some time as we carefully consider each application.
Screen
After your application has been reviewed, if you meet the qualifications for the role, a recruiter will reach out to you to start a conversation.
Interview
If you are invited for an interview, you will be scheduled to meet with the hiring manager and hiring team.
Offer
If you are extended an offer to join MassMutual and accept, your start will be contingent upon a satisfactory background check.
Hire
If you accept the offer, we will be so excited to welcome you to the MassMutual community!
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
By the numbers*
- 85% of employee respondents say they are proud to work at MassMutual
-
90
% of employee respondents say the work they do at MassMutual is meaningful - 85% of employee respondents say they feel encouraged to come up with new and better ways of doing things
*Source: 2025 MassMutual employee engagement survey
Award-Winning Culture
MassMutual is guided by a single purpose: We help people secure their future and protect the ones they love. As a company operated for the benefit of our members and participating policyowners, we are defined by mutuality and our vision to provide financial well-being for all Americans. It’s more than our company structure — it’s our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources and rely on each other when it counts.
We strive to build a thriving community where everyone is valued, included, and feels that they belong.
At MassMutual, we Live Mutual.
How We Work
MassMutual’s flexible workplace approach combines the importance of connecting in person and the flexibility of working remotely. Our hybrid model puts collaboration first with employees coming in at least three days per week to our spectacular campus settings and also enjoying the flexibility of remote Fridays, company-wide remote weeks, and a bank of flexible remote weeks to use throughout the year.
Benefits for the whole you (and your loved ones)
There’s more to your life than your job and there’s more to your aspirations than a paycheck. We take a holistic view of compensation and benefits that provides the flexibility to create a healthy balance in your life for work, family, and community. We offer the benefits you’d expect, like medical, dental, 401(k), and generous vacation time, but we also offer ones you might not expect, like three paid days for volunteering, a $1,250 annual Well-Being Wallet, and up to 320 hours of caregiver leave.
Explore some of our offerings below. Benefit details can be found here.
Why MassMutual?
Candy
Marketing Consultant
Atsam
Head of Advisor/Client Experience & Business Excellence
Erica
Head of Procurement
where we work
Springfield Office
1295 State Street, Springfield, MA
Boston Office
10 Fan Pier Blvd, Boston, MA
New York Office
2 Park Ave,
New York, NY
Virtual
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