Head of Enrollment

Location: Boston, Massachusetts preferred; hybrid work from a local Guardian office. Qualified candidates in other Guardian office locations may be considered. Up to 20% travel.

Salary: $178,690–$293,560 per year, plus potential incentive compensation.

Company

hirify.global provides group benefits and employee benefit solutions.

What you will do

• Set and execute the enterprise enrollment strategy, operating model, and participation goals across Group Benefits.
• Lead enrollment practice leaders, contracted enrollers, and external enrollment firm partnerships.
• Partner with Sales, Client Management, and Distribution to support growth, retention, and persistency.
• Use customer segmentation, communication strategies, technology, and analytics to improve enrollment effectiveness.
• Establish performance standards, reporting frameworks, operating rhythms, and accountability mechanisms.
• Build scalable, customer-centered enrollment experiences and continuously improve execution and satisfaction.

Requirements

• At least 8 years of experience in group benefits, enrollment, distribution, client management, operations, or related commercial leadership.
• Experience leading enrollment strategy, participation initiatives, field execution, or benefits engagement programs.
• Understanding of voluntary benefits, workplace benefits enrollment, broker and customer expectations, and employee participation drivers.
• Experience managing internal teams, external partners, vendors, and distributed resources in a matrixed environment.
• Strong executive communication, influence, data-driven decision-making, and team development skills.
• Must be legally authorized to work in the United States without current or future employer sponsorship.

Nice to have

• Bachelor’s degree.
• Experience in commercial insurance, financial services, employee benefits, enrollment consulting, enrollment firms, or carrier organizations.

Culture & Benefits

• Support for professional and personal goals through skill-building and leadership development.
• Philanthropic opportunities and a diverse workplace with high ethical standards.
• Contemporary, supportive, flexible, and inclusive benefits and resources for eligible full-time employees.
• Guardian may use AI tools for preliminary application screening, with an option to opt out.