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:

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 the successful candidate. In addition to salary, this role may also be eligible for annual, sales, or other incentive compensation.

Our Promise

At Guardian, you’ll have the support and flexibility to achieve your professional and personal goals.  Through skill-building, leadership development and philanthropic opportunities, we provide opportunities to build communities and grow your career, surrounded by diverse colleagues with high ethical standards.

Inspire Well-Being

As part of Guardian’s Purpose – to inspire well-being – we are committed to offering contemporary, supportive, flexible, and inclusive benefits and resources to our colleagues. Explore our company benefits at www.guardianlife.com/careers/corporate/benefits. Benefits apply to full-time eligible employees. Interns are not eligible for most Company benefits.

Equal Employment Opportunity

Guardian is an equal opportunity employer. All qualified applicants will be considered for employment without regard to age, race, color, creed, religion, sex, affectional or sexual orientation, national origin, ancestry, marital status, disability, military or veteran status, or any other classification protected by applicable law.

Accommodations

Guardian is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. Guardian also provides reasonable accommodations to qualified job applicants (and employees) to accommodate the individual's known limitations related to pregnancy, childbirth, or related medical conditions, unless doing so would create an undue hardship. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact [email protected]. Please note: this resource is for accommodation requests only. For all other inquires related to your application and careers at Guardian, refer to the Guardian Careers site.

Visa Sponsorship

Guardian Life is not currently or in the foreseeable future sponsoring employment-based visas (e.g., such as an H-1B). In order to be a successful applicant, you must be legally authorized to work in the United States, without the need for employer sponsorship/support now or at any time in the future.

Notice Regarding Guardian’s Use of Artificial Intelligence in Recruitment

As part of Guardian’s job application process, Guardian may use artificial intelligence tools (“AI Tools") to automate the sorting and filtering of information provided by applicants as part of its preliminary screening. This preliminary screening may be used to help identify applicant materials and resumes relative to their indication that the applicant meets the requirements for the specific job for which they are applying, as specified in the listing posted on Guardian’s jobs website (Careers at Guardian at https://www.guardianlife.com/careers). At Guardian, we do not use AI Tools to substantially assist or replace human judgment or discretionary decision making in our hiring process. All hiring decisions will be made by Guardian colleagues.

Please be aware that if you apply for a specific position with Guardian, you will have the choice of opting out of Guardian’s use of AI Tools during the job application process. If you would like to request an alternative process that does not utilize AI Tools or would like to request a reasonable accommodation, within ten business days of your position application, you must email your request to [email protected], making sure to provide your name and job requisition identification number. Guardian will retain your applicant materials and resume and all information therefrom in accordance with Guardian’s document retention policy, a copy of which you may request via [email protected].

Additionally, at applicable times, Guardian will make public the most recent bias audit results for such AI tools, which may be found here. 

Current Guardian Colleagues: Please apply through the internal Jobs Hub in Workday.