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Head of Enrollment

September 7, 2026

<div>Head of EnrollmentAs 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<ul><li>A strategic and commercially minded leader who understands the critical role enrollment plays in driving customer value, employee engagement, participation outcomes, and business growth.</li><li>An influential relationship builder who establishes credibility across sales, client management, brokers, customers, enrollment partners, and senior leaders.</li><li>A customer-focused problem solver who balances strategic thinking with operational excellence to deliver exceptional enrollment experiences.</li><li>A collaborative leader who thrives in a matrixed environment and brings stakeholders together around shared goals and measurable outcomes.</li><li>A data-driven decision maker who leverages insights, trends, and analytics to improve participation, execution, and customer outcomes.</li><li>An effective communicator who can simplify complexity, influence diverse audiences, and lead through change.</li><li>A people-first leader who develops talent, creates accountability, and builds high-performing teams focused on delivering results.</li></ul>You Have<ul><li>Minimum of 8 years of experience in group benefits, enrollment, distribution, client management, operations, or a related commercial leadership role.</li><li>Proven experience leading enrollment strategy, participation improvement initiatives, field execution, or benefits engagement programs.</li><li>Deep understanding of voluntary benefits, workplace benefits enrollment dynamics, broker and customer expectations, and the factors that influence employee participation.</li><li>Experience managing internal teams, external partners, vendors, and distributed resources within a matrixed environment.</li><li>Demonstrated ability to collaborate effectively across sales, client management, operations, technology, marketing, product, and service organizations to deliver business impact.</li><li>A data-driven mindset with the ability to leverage enrollment analytics, participation trends, and customer insights to identify opportunities and improve outcomes.</li><li>Strong executive presence, communication skills, and the ability to influence senior leaders, field stakeholders, brokers, customers, and external partners.</li><li>The ability to translate enterprise strategy into scalable, disciplined execution while adapting to evolving customer needs, market conditions, and business priorities.</li><li>Proven success recruiting, developing, coaching, and inspiring diverse, high-performing teams focused on accountability, collaboration, and measurable results.</li><li>Experience within commercial insurance, financial services, employee benefits, enrollment consulting, enrollment firms, or carrier organizations preferred.</li></ul>You Will<ul><li>Be accountable for Guardian's overall enrollment strategy, execution model, and participation outcomes across Group Benefits.</li><li>Lead and develop enrollment practice leaders, directly contracted enrollers, and external enrollment firm partnerships to deliver consistent, high-quality enrollment experiences.</li><li>Partner closely with Sales, Client Management, and Distribution leaders to develop enrollment strategies that drive new business growth, customer retention, and persistency results.</li><li>Drive participation and enrollment effectiveness by leveraging data, customer segmentation, communication strategies, enrollment technology, and disciplined field execution.</li><li>Establish clear performance standards, operating rhythms, reporting frameworks, and accountability mechanisms for both internal and external enrollment resources.</li><li>Build scalable enrollment capabilities that support customers of varying sizes, complexity levels, industries, and benefit offerings.</li><li>Strengthen relationships with enrollment firms and strategic partners to ensure quality execution, operational consistency, and alignment with Guardian's growth objectives.</li><li>Champion customer-centric and employee-centered enrollment experiences that increase understanding, engagement, and participation in Guardian's benefit solutions.</li><li>Leverage enrollment insights and market trends to continuously improve enrollment practices, participation outcomes, and overall customer satisfaction.</li><li>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.</li><li>Foster a culture of collaboration, accountability, innovation, and continuous improvement across the enrollment organization and partner ecosystem.</li></ul>Education:<ul><li>Bachelor’s degree, preferred</li></ul>Work Arrangement & Travel Requirements:<ul><li>Boston, MA is the preferred location for this role; however, qualified candidates located in other Guardian office locations will be considered.</li><li>The work arrangement will be "hybrid" out of a local Guardian office</li><li>Up to 20% travel</li></ul>Salary Range:$178,690.00 - $293,560.00The 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.</div>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...