Senior Associate, Enroller Manager

Location Designation: Fully Remote
Role Overview:
The Enroller Manager is a senior individual-contributor role within New York Life Group Benefit Solutions, accountable for the strategic planning, execution, and continuous improvement of enrollment staffing operations. This role leads the end-to-end lifecycle of vendor enrollers (benefit counselors), ensuring enrollment events are staffed with high-quality, credentialed professionals who deliver an exceptional client and participant experience.
Operating with a high degree of autonomy, the Enroller Manager serves as a subject matter expert (SME) for enrollment staffing strategy, group benefits enrollment practices, and vendor performance management. The role partners closely with Sales, Service, and Field Leadership to align staffing decisions with business priorities, cost efficiency, and client complexity.
What You'll Do:
Strategic Staffing & Workforce Planning

• Independently forecast enrollment staffing demand across assigned markets, factoring in seasonality, client complexity, geographic considerations, and enrollment modality.
• Develop and execute proactive recruitment strategies to maintain a deep, ready bench of experienced enrollers.
• Evaluate staffing models and recommend improvements to optimize cost, quality, and coverage.

Recruitment, Hiring & Vendor Oversight

• Lead end-to-end recruitment, selection, onboarding, and performance management of vendor enrollers.
• Apply expert judgment to assess qualifications, licensing, and fit.
• Maintain strong professional relationships with experienced enrollers and insurance agents.

Enrollment Execution & Account Readiness

• Partner with Sales Offices and internal teams to ensure enrollment readiness.
• Deliver account-specific training and briefings.
• Anticipate and resolve enrollment risks independently.

SME Leadership & Cross-Functional Influence

• Act as a trusted advisor to Sales and Service teams.
• Educate partners on staffing best practices.
• Contribute thought leadership to enrollment strategy.

Reporting, Compliance & Continuous Improvement

• Ensure post-enrollment reconciliation and expense compliance.
• Analyze performance trends and recommend improvements.
• Lead or support special projects.

What You'll Bring:

• Minimum 3 years of experience in enrollment staffing or group benefits operations.
• Working knowledge of group benefits and enrollment mechanics.
• Established insurance agent or enroller network preferred.
• Strong decision-making, organizational, and communication skills.
• Technology-savvy with demonstrated ability to use tools such as Smartsheet, payroll and timekeeping systems, Adobe applications, and emerging AI-enabled tools to improve operational efficiency, reporting accuracy, and decision-making.

Preferred Qualifications

• Bachelor's degree or equivalent experience.
• Active insurance license or ability to obtain.
• Advanced Microsoft Office proficiency.

Pay Transparency
Salary Range: $63,000 - $70,000
Overtime eligible: Exempt
Discretionary bonus eligible: Yes
Sales bonus eligible: No
Actual base salary will be determined based on several factors but not limited to individual's experience, skills, qualifications, and job location. Additionally, employees are eligible for an annual discretionary bonus. In addition to base salary, employees may also be eligible to participate in an incentive program.
Company Overview
At New York Life, our 180-year legacy of purpose and integrity fuels our future. As we evolve into a more technology-, data-, and AI-enabled organization, we remain grounded in the values that drive lasting impact.
Our diverse business portfolio creates opportunities to make a difference across industries and communities-inviting bold thinking, collaborative problem-solving, and purpose-driven innovation. Here, you'll find the rare balance of long-standing stability and forward momentum, supported by an inclusive team that honors tradition while embracing progress.
As a Fortune 100 mutual company, we offer a place to grow your skills, contribute to meaningful work, and deliver solutions that matter. Your ideas drive what's next, and your growth powers it.
Our Benefits
We provide a full package of benefits for employees - and have unique offerings for a modern workforce, including leave programs, adoption assistance, and student loan repayment programs. Based on feedback from our employees, we continue to refine and add benefits to our offering, so that you can flourish both inside and outside of work.Click hereto discover more about our comprehensive benefit options or visit our NYL Benefits Site.
Our Commitment to Inclusion
At New York Life, fostering an inclusive workplace is fundamental to who we are and how we serve our communities. We have a longstanding commitment to creating an environment where individuals can contribute their best and succeed together. This foundation is rooted in our core values of humanity and integrity, ensuring that every employee feels valued and supported. By embracing a broad range of perspectives and experiences, we achieve greater success and fulfill our promise of providing financial security and peace of mind to families across all communities. Click here to learn more about New York Life's leadership in this space.
Recognized as one of Fortune's World's Most Admired Companies, New York Life is committed to improving local communities through a culture of employee giving and volunteerism, supported by the Foundation. We're proud that due to our mutuality, we operate in the best interests of our policy owners. To learn more about career opportunities at New York Life, please visit the Careers page of www.NewYorkLife.com.
Visit our LinkedIn to see how our employees and agents are leading the industry and impacting communities.
Visit our Newsroom to learn more about how our company is constantly evolving to meet our clients' and employees' needs.
Job Requisition ID: 93324