Sr. Associate, Benefits - Health & Welfare

New York Life Insurance Co.; New York (NY); Hybrid; USD 81,000 - 104,000; Full time

Job summary

New York Life Insurance Co. is seeking a Sr. Associate, Benefits – Health & Welfare to manage eligibility, deductions, and complex benefit cases. The role partners with vendors to ensure accurate data and high-quality employee experiences.

Hybrid role with 3 days onsite. Requires 2–4+ years in benefits or HR operations, strong Excel skills, and excellent communication. Responsible for audits, data validation, and process improvements within a fast-paced environment.

Qualifications

• Bachelor’s degree preferred; 2–4+ years in benefits administration, HR ops, payroll, or related field in a large organization.
• Working knowledge of Health & Welfare benefit plans and administration.
• Strong Excel skills with large data sets, formulas, reconciliations.
• Strong analytical and problem-solving skills with ability to research complex issues.
• Highly organized, detail-oriented, adaptable; manage high volume of work and shifting priorities.
• Excellent written and verbal communication; professional with employees, agents, and vendors.

Responsibilities

• Administer employee and agent benefit eligibility, contributions, enrollments, terminations, refunds, and related transactions.
• Manage weekly Health & Welfare deduction files; analyze and reconcile data; investigate variances.
• Prepare and coordinate benefit statements and communications related to status changes.
• Manage appeals, COBRA subsidies, and Executive Life Insurance payments; ensure documentation and processing.
• Research and resolve complex benefits cases; coordinate with internal partners and external vendors.
• Coordinate biannual benefit earnings update and data validation.
• Perform Annual Enrollment website testing and issue resolution.
• Complete year-end and new-year validation for accurate payroll deductions.
• Perform MAR/SOX audits to ensure compliance with controls.
• Data analysis, reconciliations, testing, and quality-control of benefit data.
• Manage multiple responsibilities, deadlines, and changing priorities.

Skills

Excel proficiency

Analytical thinking

Communication

Independent work

Attention to detail

Education

Bachelor’s degree preferred

Tools

Microsoft Excel

Job description

Location Designation: Hybrid - 3 days per week

The Sr. Associate, Benefits – Health & Welfare is a key member of the Benefits Services team responsible for the accurate and timely administration of Health & Welfare benefits for New York Life employees and agents.

This role manages a broad range of benefit administration activities, including eligibility, contributions, payroll deductions, agent benefits, benefit earnings, COBRA subsidies, appeals, executive life insurance payments, and complex or escalated benefit cases. The Sr. Associate works closely with internal partners and external benefit vendors to research and resolve issues, maintain accurate benefit data, and deliver a high-quality experience to employees and agents.

The position operates in a fast-paced, high-volume environment and requires strong ownership, attention to detail, sound judgment, and the ability to manage multiple priorities and deadlines. The successful candidate will work independently within established processes while identifying issues, coordinating solutions, and escalating matters appropriately.

What You’ll Do

• Administer employee and agent benefit eligibility, contributions, enrollments, terminations, refunds, and related transactions.
• Manage weekly Health & Welfare benefit deduction files, using Excel to analyze and reconcile data, investigate variances, and coordinate corrections.
• Prepare and coordinate benefit statements and related communications associated with changes in an employee’s job or employment status.
• Manage Health & Welfare appeals, COBRA subsidy administration, and Executive Life Insurance benefit payments, including documentation, and processing.
• Research and resolve complex and escalated Health & Welfare cases, providing professional and responsive support to employees and agents and coordinating with internal partners and external vendors as needed.
• Coordinate the biannual benefit earnings update and associated data validation.
• Perform Annual Enrollment website and system testing and support resolution of identified issues.
• Complete year-end and beginning-of-year validation to ensure benefit elections and deductions are accurately reflected in the first payroll of the year.
• Perform MAR/SOX audits to ensure compliance with internal controls and regulatory requirements.
• Perform data analysis, reconciliations, testing, and quality-control activities to support the integrity of benefit data and processes.
• Manage multiple operational responsibilities, deadlines, and cases while adapting to changing priorities and business needs.
• Build effective relationships with employees, agents, internal partners, and external vendors, using sound judgment and professionalism to de-escalate and resolve benefit-related concerns.
• Identify and support process improvements that strengthen operational efficiency, controls, and the employee and agent benefit experience.
• Support Benefits projects, implementations, testing, and other initiatives as needed.

What You’ll Bring

• Bachelor’s degree preferred, with 2–4+ years of experience in benefits administration, HR operations, payroll, or a related field within a large, complex organization preferred.
• Working knowledge of Health & Welfare benefit plans and administration.
• Strong Microsoft Excel skills, including experience with large data sets, formulas, file comparisons, and reconciliations.
• Strong analytical and problem-solving skills, with the ability to research complex issues and drive them to resolution.
• Highly organized, detail-oriented, and adaptable, with the ability to manage a high volume of work, competing deadlines, and changing priorities in a fast-paced environment.
• Excellent written and verbal communication skills, with the patience, professionalism, and judgment to work effectively with employees, agents, internal partners, and external vendors, including de-escalating challenging benefit situations.
• Ability to work independently, take ownership, and exercise sound judgment, including recognizing when escalation is appropriate.
• Collaborative and service-oriented approach with a commitment to confidentiality and a positive employee and agent experience.

What Success Looks Like

Success in this role means taking ownership, delivering accurate and timely results, and effectively managing complex benefit matters in a fast-paced environment. The Sr. Associate demonstrates sound judgment, agility, and a service-oriented mindset while collaborating across teams and with external partners to strengthen benefit operations and the employee and agent experience.

Pay Transparency

Salary Range: $81,000-$104,000

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 here to 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.