Executive Searches
 

Head of Enrollment & Marketing

 

 

Jay D'Aprile

Executive Vice President

Leading Employee Benefits Insurance Carrier

 

Position Summary:

The Head of Enrollment & Marketing serves as a senior leader responsible for shaping and executing the enrollment and marketing strategy for a large-scale employee benefits business. Reporting to enterprise leadership and leading a team of approximately 100, this role drives profitable growth and persistency by integrating strategic planning, marketing innovation, and customer engagement. The executive partners closely with Product, Sales, Operations, Claims, Technology, and Enterprise Marketing to translate enterprise priorities into cohesive, digital-first storytelling and differentiated customer experiences.
 
The ideal candidate will bring 10+ years of progressive leadership experience in marketing, enrollment strategy, or business development within the Group, Voluntary or Worksite lines of business. This leader has a proven track record of building and scaling enterprise initiatives, leveraging analytics and customer insights to improve participation, retention, and profitability. Strong executive presence, cross-functional influence, and the ability to translate complex data into clear, compelling narratives are essential, along with deep understanding of the employee benefits landscape and broker dynamics.

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