Director, Worksite Re-Enrollment (Hiring Immediately)

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

• High School Diploma

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-focused mindset

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

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