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Director - Benefits and Leave Administration

YAI
Manhattan, NY Full Time
POSTED ON 11/23/2025
AVAILABLE BEFORE 12/20/2025

Under the direction of the Chief Human Resources Officer (CHRO), the Director of Benefits and Leave Administration is responsible for the design, implementation, delivery and oversight of all employee benefit programs and leaves of absence, including workers compensation and employee wellness initiatives. Leads the analysis, design and evaluation of benefit programs and makes data-driven recommendations regarding changes, offerings and administration that allow YAI to offer robust, cost-effective and competitive plans to attract and retain a quality workforce. Serves as primary liaison with benefit and leave-related vendors and external partners, including benefits broker and third-party administrators. Ensures compliance of various benefit programs and leave administration with all government regulations and other local or legal requirements, preparing and filing required legal reports. Regularly collaborates with YAI and affiliate program and administrative leadership, human resources directors and staff and other key stakeholders to develop a strong understanding of organizational structure, needs and operations to support implementation of meaningful initiatives and programs. Directly supervises benefits staff, providing guidance and ensuring quality service, access to resources and information and appropriate, timely processing of benefit and leave-related requests and inquiries.


Key/Essential Functions & Responsibilities:


  • Designs long-term strategy for benefits and regularly evaluates all benefit plans to ensure they are cost-effective, competitive and meet the needs of both the employees and the organization in collaboration with CHRO, other HR directors and staff and broker.
  • Works closely with the CHRO to assess current state of the organization and builds productive relationships with key stakeholders and leaders, identifying areas for improvement, making recommendations for changes, initiatives and enhancements regarding benefits and leaves of absence administration and programs.
  • Ensures benefit and leave-related programs are appropriately integrated and effective in supporting the overall mission, goals and objectives of the agency and are administered in compliance with all applicable Federal, State and/or Local laws, regulations and requirements.
  • Leads planning, development and implementation of new initiatives or updates to policies, procedures or education relating to benefits, leaves, retirement and other related areas.
  • Stays abreast of relevant laws, regulations and best practices in benefits and leaves administration, serving as an internal consultant and strategic advisor to the CHRO, HR staff and Senior Leadership Team.
  • Manages the negotiation/renewal of contracts with third-party providers including brokers, consultants and/or vendors, ensuring cost-effectiveness, performance results and appropriate service levels; reviews vendor market and assesses new products and/or vendors.
  • Serves as primary liaison for all third-party providers regarding benefits, retirement, leaves, wellness and employee assistance-related inquiries, implementations, escalated claim issues and requests; maintains regular contact to monitor performance and compliance with contracts, including through periodic vendor meetings.
  • Plans and directs implementation and administration of employee benefit programs such as health insurance, disability insurance, life insurance, employee assistance, retirement and other plans.
  • Maintains responsibility for leave and Worker’s Compensation administration, including collaboration with third-party administrators and carriers and oversight of day-to-day processing, updates and inquiries handled by benefits team to ensure compliance with timelines and documentation requirements for all applicable regulations for all leaves of absence (FMLA, PFL, CFRA, DBL, etc.).
  • Oversees employee wellness program and implements new initiatives to motivate employees to maintain and improve their health in innovative ways and manages other incentives or programs, including the tuition reimbursement program, word of mouth referral program and employee discounts.
  • Directs and monitors activities of the benefits team, ensuring they provide excellent service and useful education and resources to employees regarding an array of benefits and leaves questions, resolve problems related to access to or payment of benefits, orient newly eligible employees and process enrollments, changes, and loan requests in a timely manner.
  • Provides guidance and assistance with the resolution of a wide array of benefit and leave-related questions, concerns and issues including policy inquires to staff at all levels of the organization, including assisting individual employees with complex or sensitive inquiries, as needed.
  • Ensures appropriate, consistent and compliant processes are in place to support evaluation, development and implementation of reasonable accommodations as requested by employees, including those at returns from leaves of absence and/or for other covered disabilities, in collaboration with external partners, managers and other HR staff.
  • Leads the annual benefit plan renewal and open enrollment cycles including market analysis, plan design, cost modeling, stakeholder management and communication in collaboration with CHRO, broker and other HR directors; conducts ongoing analyses of benefits experience for cost-control, funding alternatives and risk-assessment factors.
  • Facilitates system configuration for benefits, leaves and retirement, including creation of and/or updates to plans, deductions and integrations in Workday and oversees the transfer of data to external vendors, plan providers, auditors and consultants in close collaboration with HCM team.
  • Manages all compliance, filing, reports and audits related to benefit programs including health and welfare, wellness and reporting of 5500 and distribution of SARs.
  • Prepares and communicates information to shareholders, employees and former employees about benefit programs, procedures, changes and government-mandated disclosures.
  • Analyzes and evaluates services, coverage and options available through insurance and investment companies.
  • Processes and reviews benefit-related invoices for accuracy and resolves discrepancies, in collaboration with finance department and HR team.
  • Participates in development of the organization’s staffing budget and the budget for the Human Resources department and in the selection process and education of HR staff, as requested.
  • Performs all other duties, as assigned.


Minimum Qualification Requirements including education, experience, licensure/certification, etc. and essential physical capabilities (e.g. lifting, assisting lifting, standing, etc.)


  • Bachelor’s degree in Human Resources, Business Administration, or related field; and
  • Ten (10) years of human resources experience involving day-to-day administration of employee benefits, retirement, wellness, leaves of absence and/worker’s compensation including at least five (5) years in the oversight and administration of related programs and staff; and
  • Thorough knowledge of Federal and multi-state employment law specifically in the realm of benefits, leaves of absence and retirement including ACA, FMLA, ADA, EEOC, ERISA, HIPAA and applicable state and local regulations in New York State, New York City, New Jersey and/or California; or
  • Satisfactory equivalent combination of education, experience and/or training.
  • Excellent interpersonal, verbal and written communication skills, including the ability to regularly engage and build effective working relationships with leadership, staff and external stakeholders at varying levels.
  • Exceptional supervisory and leadership skills and ability to effectively manage, coach and support teams through hands-on support.
  • Strong critical thinking, analytical skills and problem-solving ability, particularly in ambiguous, complex and sensitive situations.
  • Ability to work effectively in a fast-paced environment, appropriately prioritizing dynamic priorities to meet deadlines and other requirements.
  • Strong computer skills including proficiency with HCM/ERP systems, ideally Workday.
  • Advanced knowledge of Microsoft Office Suite, including charts, formulas, v-lookups and pivot tables in Excel and advanced formatting and review functionality in Word.
  • Ability to report on-site to our Manhattan office regularly and to occasionally travel to other YAI locations across the NYC metropolitan area, as requested.
  • Ability to meet essential physical demands of position, including the ability to sit for extended periods, lift and carry files or documents weighing up to 10 pounds and move around the office.


Preferred Qualification Requirements (desired requirements beyond MQRs above)


  • Master’s degree and/or professional certification in Human Resources (PHR/SPHR or SHRM-CP/SHRM-SCP)
  • Previous experience with administration of self-insured/self-funded benefit plans

Ability to configure benefit plans, rate tables, enrollment events and/or payroll deductions and earnings codes in Workday HCM system

Salary : $120,000 - $140,000

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