Head of Enrollment

About this role

Head of Enrollment

As Head of Enrollment, you will lead the enterprise enrollment function for Guardian Group Benefits and be accountable for driving enrollment success, participation, and employee engagement across our customer base. You will set the strategic direction for Guardian’s enrollment capabilities and ensure our enrollment model delivers measurable impact for customers, brokers, sales teams, and client management partners.

You will report directly to the Head of Group Benefits Distribution and are accountable for building and leading a high-performing enrollment organization. This includes oversight of enrollment practice leads, directly contracted enrollers, and Guardian’s partnership network with enrollment firms. You will work closely with sales and client management leadership to maximize participation, strengthen the customer experience, and ensure enrollment is a clear differentiator in the market.

You Are • A strategic and commercially minded leader who understands the critical role enrollment plays in driving customer value, employee engagement, participation outcomes, and business growth.

• An influential relationship builder who establishes credibility across sales, client management, brokers, customers, enrollment partners, and senior leaders.

• A customer-focused problem solver who balances strategic thinking with operational excellence to deliver exceptional enrollment experiences.

• A collaborative leader who thrives in a matrixed environment and brings stakeholders together around shared goals and measurable outcomes.

• A data-driven decision maker who leverages insights, trends, and analytics to improve participation, execution, and customer outcomes.

• An effective communicator who can simplify complexity, influence diverse audiences, and lead through change.

• A people-first leader who develops talent, creates accountability, and builds high-performing teams focused on delivering results.

You Have • Minimum of 8 years of experience in group benefits, enrollment, distribution, client management, operations, or a related commercial leadership role.

• Proven experience leading enrollment strategy, participation improvement initiatives, field execution, or benefits engagement programs.

• Deep understanding of voluntary benefits, workplace benefits enrollment dynamics, broker and customer expectations, and the factors that influence employee participation.

• Experience managing internal teams, external partners, vendors, and distributed resources within a matrixed environment.

• Demonstrated ability to collaborate effectively across sales, client management, operations, technology, marketing, product, and service organizations to deliver business impact.

• A data-driven mindset with the ability to leverage enrollment analytics, participation trends, and customer insights to identify opportunities and improve outcomes.

• Strong executive presence, communication skills, and the ability to influence senior leaders, field stakeholders, brokers, customers, and external partners.

• The ability to translate enterprise strategy into scalable, disciplined execution while adapting to evolving customer needs, market conditions, and business priorities.

• Proven success recruiting, developing, coaching, and inspiring diverse, high-performing teams focused on accountability, collaboration, and measurable results.

• Experience within commercial insurance, financial services, employee benefits, enrollment consulting, enrollment firms, or carrier organizations preferred.

You Will • Be accountable for Guardian's overall enrollment strategy, execution model, and participation outcomes across Group Benefits.

• Lead and develop enrollment practice leaders, directly contracted enrollers, and external enrollment firm partnerships to deliver consistent, high-quality enrollment experiences.

• Partner closely with Sales, Client Management, and Distribution leaders to develop enrollment strategies that drive new business growth, customer retention, and persistency results.

• Drive participation and enrollment effectiveness by leveraging data, customer segmentation, communication strategies, enrollment technology, and disciplined field execution.

• Establish clear performance standards, operating rhythms, reporting frameworks, and accountability mechanisms for both internal and external enrollment resources.

• Build scalable enrollment capabilities that support customers of varying sizes, complexity levels, industries, and benefit offerings.

• Strengthen relationships with enrollment firms and strategic partners to ensure quality execution, operational consistency, and alignment with Guardian's growth objectives.

• Champion customer-centric and employee-centered enrollment experiences that increase understanding, engagement, and participation in Guardian's benefit solutions.

• Leverage enrollment insights and market trends to continuously improve enrollment practices, participation outcomes, and overall customer satisfaction.

• Serve as a key member of the Distribution Leadership Team, helping shape the strategic direction of the organization and advancing Guardian's ability to deliver market-leading enrollment outcomes.

• Foster a culture of collaboration, accountability, innovation, and continuous improvement across the enrollment organization and partner ecosystem.

Education : • Bachelor’s degree, preferred

Work Arrangement & Travel Requirements: • Boston, MA is the preferred location for this role; however, qualified candidates located in other Guardian office locations will be considered.

• The work arrangement will be "hybrid" out of a local Guardian office

• Up to 20% travel

Salary Range:

$178,690.00 - $293,560.00 The salary range reflected above is a good faith estimate of base pay for the primary location of the position. The salary for this position ultimately will be determined based on the education, experience, knowledge, and abilities of th

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