Director, Worksite Re-Enrollment

About the role

The Director, Worksite Re-Enrollment leads a high-performing team focused on retaining and growing revenue across existing employer groups through effective renewals and re-enrollment strategies. This role plays 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.

Responsibilities

• 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.

Requirements

• 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.

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.
• Data-driven approach to leadership, including use of dashboards, participation analytics, and performance metrics.
• Bachelor’s degree.

Skills

• Strategic thinking and execution.
• Team leadership and development.
• Customer relationship management.
• Voluntary insurance product knowledge.
• Renewal and re-enrollment expertise.
• Consultative selling and influencing skills.
• Data analysis and reporting.

Benefits

MassMutual offers a comprehensive benefits package designed to support the whole you and your loved ones. This includes:

• Medical, dental, and vision coverage.
• A 401(k) retirement plan with company matching.
• Generous vacation time.
• Three paid days for volunteering.
• A $1,250 annual Well-Being Wallet.
• Up to 320 hours of caregiver leave.

Pay

$121,800 - $159,800

Schedule

Hybrid schedule with at least three days per week in the office and remote Fridays, company-wide remote weeks, and a bank of flexible remote weeks to use throughout the year.