Director, Worksite Re-Enrollment

Director, Worksite Re-Enrollment

Location:

Springfield or Boston.

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.

• 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.

• 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.

• 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.
• 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.

• 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.

Salary Range: $121,800-$159,800.

• At Mass Mutual, we focus on ensuring fair equitable pay, by providing competitive salaries, along with incentive and bonus opportunities for all employees.
• Your total compensation package is designed to reward performance and align with company goals.