Director, Renewal & Enrollment Strategy

MassMutual; Springfield (MA); On-site; USD 150,000 - 190,000; Full time

Benefits offered by this job

Not specified

Job summary

MassMutual seeks a Director, Worksite Re-Enrollment to lead a high-performing team focused on renewals and re-enrollment strategies across a defined employer group book. The role drives participation, product adoption, and superior customer experiences for producers, brokers, and clients.

You will guide renewal strategy, enrollment execution, and cross-functional collaboration with Sales, Service, Implementation, Underwriting, and Operations.

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

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.

Skills

Leadership

Team leadership

Revenue growth

Education

Bachelor's degree

Job description

MassMutual seeks a Director, Worksite Re-Enrollment to lead a high-performing team focused on renewals and re-enrollment strategies across a defined employer group book. The role drives participation, product adoption, and superior customer experiences for producers, brokers, and clients.

You will guide renewal strategy, enrollment execution, and cross-functional collaboration with Sales, Service, Implementation, Underwriting, and Operations.