Assistant Director of Benefits- Westchester County NY

Job Description

ENT and Allergy Associates is seeking a self-motivated, people-friendly full time Assistant Director of Benefits for our organization.

Salary: $130,000 -$140,000

Full time in office, Tarrytown NY

JOB SUMMARY:

As the Assistant Director of Benefits, you will be responsible for supporting the strategic planning and execution of our organization's benefits programs. Reporting directly to the Vice President, Human Resources, you will oversee the design, administration, and communication of employee benefit plans, including health insurance, retirement plans, leave management, and wellness initiatives while ensuring compliance with all applicable laws and regulations.

This role also requires a strong functional understanding of Workday Benefits and Absence, with the expectation that the individual will operate as a highly capable end user, leveraging the system effectively, supporting issue resolution, and partnering with HRIS and external vendors to ensure a seamless and efficient benefits administration environment.

We are seeking a creative, highly motivated, and results-driven professional who possesses a comprehensive understanding of benefits. Your exceptional managerial, analytical, and communication skills will be crucial in managing and developing high-performing teams, fostering a collaborative and inclusive work environment, and promoting the professional growth and development of our employees.

STRATEGIC RESPONSIBILITIES:

• Support the development and execution of a comprehensive employee benefits strategy that aligns with organizational goals.
• Demonstrate a strong functional understanding of Workday Benefits and Absence, ensuring the system is leveraged effectively to support business needs and employee experience.
• Partner closely with HRIS, Payroll, Finance, and external vendors to translate business requirements into system needs, supporting enhancements and process improvements.
• Manage the benefits team, providing guidance, support, and fostering a high-performance culture.
• Demonstrate a strong functional understanding of Workday Benefits and Absence, ensuring the system is leveraged effectively to support business needs and employee experience.
• Partner closely with HRIS, Payroll, Finance, and external vendors to translate business requirements into system needs, supporting enhancements and process improvements.
• Stay informed about industry trends, best practices, emerging technologies, and regulations related to benefits, and leverage this knowledge to drive innovation, maintain compliance, and enhance competitiveness within our benefits functions.
• Monitor and report on key metrics and performance indicators related to employee benefits, providing insights and recommendations for improvement.

OPERATIONAL RESPONSIBILITIES:

• Manage all aspects of benefits administration including health insurance, retirement plans, leave management, wellness initiatives, plan design, enrollment, vendor management, and employee communication to ensure efficient, accurate and timely delivery of services.
• Operate as a highly proficient Workday user for Benefits and Absence, including life events, enrollments, and leave processes.
• Troubleshoot and resolve benefits and leave-related issues by identifying root causes, validating data, and partnering with HRIS or external vendors (e.g., Workday support, implementation partners) for resolution.
• Participate in system enhancements and Workday releases, providing business input, supporting testing (UAT), and validating outcomes.
• Ensure compliance with federal, state, and local regulations, including but not limited to ERISA, ACA, HIPAA, and COBRA.
• Provide guidance and support to employees regarding benefits options, resolving complex issues, and fostering a positive employee experience.
• Maintain strong relationships with benefit plan vendors, ensuring effective contract management and service level agreements.
• Conduct regular audits and reconciliations to ensure data integrity, compliance with internal controls, and identify/mitigate potential risks.
• Implement and maintain benefits policies, procedures, and systems to streamline processes, enhance data accuracy, and improve operational efficiency.
• Generate reports, metrics, and analysis (leveraging Workday reporting tools and dashboards) to inform decision-making and provide insights to senior leadership.

QUALIFICATIONS:

• 10 years of experience in benefits, with deep knowledge of health, retirement, and leave programs, including strong expertise in retirement plan design and administration across defined contribution plans (e.g., 401(k)) and defined benefit plans such as cash balance plans, with an understanding of plan funding, compliance, and vendor oversight.
• Strong communication skills, fostering employee understanding, engagement, and utilization of benefits resources, while effectively managing high-performing teams and promoting professional growth and development.
• Experience in healthcare organizations strongly preferred, particularly within multi-site, multi-state environments, with an understanding of complex workforce structures and varying regulatory and operational requirements.
• Demonstrated ability to effectively utilize Workday Benefits and/or Absence modules as a power user, including strong understanding of system workflows, life events, and enrollments.
• Ability to troubleshoot system and data issues, identify root causes, and effectively partner with technical teams for resolution (without direct configuration responsibility).
• Familiarity with benefits data flows, vendor integrations, and eligibility file structures (e.g., understanding inputs/outputs, not building them).
• Strong analytical and reporting skills, including experience leveraging Workday reporting tools and/or advanced Excel.
• Excellent understanding of federal, state, and local compliance requirements.
• Successful vendor management experience, ensuring effective contract management, service level agreements, and cost optimization.
• Proficient in using HRIS software (Workday)

Benefits:

We offer a competitive compensation package, including:

• Medical, Dental, and Vision insurance
• Company‑paid long‑term disability
• Flexible Spending Account (FSA)
• Company‑paid life insurance and voluntary life insurance
• 401(k)
• Pet insurance

Please Note: ENT and Allergy Associates of Texas is an E-Verify employer

Company Description:

ENT and Allergy Associates is the largest and most comprehensive ear, nose, throat, allergy and audiology practice in the nation with 60 offices and over 300 physicians in New York, New Jersey, and Texas. Each ENT and Allergy Associates clinical location provides access to a full complement of services, including General Adult and Pediatric ENT, Voice and Swallowing, Facial Plastics and Reconstructive Surgery, Disorders of the Inner Ear and Dizziness, Asthma, Clinical Immunology, Diagnostic Audiology, Hearing Aid dispensing, Sleep and CT Services. ENTA has a clinical alliance with The Mount Sinai Hospital for the treatment of diseases of the head and neck and esophageal cancer and a partnership with the American Cancer Society to educate and treat patients with smoking disorders and cancer. The Practice has also expanded its clinical capabilities to include advanced Immunodeficiency trials.

To learn more about the benefits of ENT and Allergy Associates, or to conveniently find an ENT doctor or Allergy Doctor and then easily book an appointment at the nearest New York or New Jersey location, please visit: www.entandallergy.com.