Director, Worksite Re-Enrollment

TL;DR

Director, Worksite Re-Enrollment: Leading a high-performing team to drive revenue growth and retention across employer groups with an accent on renewal strategy, enrollment execution, and stakeholder management. Focus on building strong relationships with producers and brokers, optimizing enrollment processes, and delivering data-driven customer experience outcomes.

Location: Must be based in or able to work from Springfield, MA or Boston, MA

Salary: $121,800–$159,800

Company

hirify.global is a purpose-driven financial services organization focused on long-term impact, integrity, and stewardship.

What you will do

• Develop and execute the overall re-enrollment strategy, roadmap, and timelines.
• Lead, coach, and develop a high-performing team focused on renewal execution and revenue growth.
• Set clear performance expectations and translate goals into actionable priorities.
• Maintain and grow relationships with top-performing producers and brokers.
• Collaborate with sales, service, and operations teams to drive enrollment adoption.
• Conduct root-cause analysis and implement process improvements to enhance customer experience.

Requirements

• 7+ years of experience in workplace/group benefits, including sales, account management, or renewals.
• 3+ years of experience delivering measurable revenue results in a sales or revenue-generating environment.
• Proven experience leading and developing teams, including performance management and coaching.
• Ability to travel up to 15% of the time.
• Strong consultative selling and influencing skills.
• Bachelor’s degree.

Nice to have

• Experience with voluntary insurance products such as group whole life, accident, critical illness, hospital indemnity, or long-term care.
• Experience leading renewals and re-enrollment efforts for employer groups.
• Data-driven approach to leadership using dashboards and performance metrics.

Culture & Benefits

• Collaborative environment that values diverse perspectives.
• Access to continuous learning, development, and internal networks.
• Employee-led communities and forums for inclusion and connection.
• Culture grounded in integrity, responsibility, and stewardship.