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

Salary Range:

$121,800-$159,800

At MassMutual, we focus on ensuring fair equitable pay, by providing competitive salaries, along with incentive and bonus opportunities for all employees. Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component.

Why Join Us.

We’ve been around since 1851. During our history, we’ve learned a few things about making sure our customers are our top priority. In order to meet and exceed their expectations, we must have the best people providing the best thinking, products and services. To accomplish this, we celebrate an inclusive, vibrant and diverse culture that encourages growth, openness and opportunities for everyone. A career with MassMutual means you will be part of a strong, stable and ethical business with industry leading pay and benefits. And your voice will always be heard.

We help people secure their future and protect the ones they love. As a company owned by our policyowners, we are defined by mutuality and our vision to put customers first. 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. At MassMutual, we Live Mutual.

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

If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.

At MassMutual, we focus on ensuring fair, equitable pay by providing competitive salaries, along with incentive and bonus opportunities for all employees. Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component. For more information about our extensive benefits offerings please check out our Total Rewards at a Glance.