Full-Time

Director – Benefits and Leave Administration

Posted on 11/7/2025

Yai

Yai

11-50 employees

AI-powered platform for content quality control

Compensation Overview

$120k - $140k/yr

Union City, NJ, USA

In Person

On-site in Manhattan required; occasional travel to other NYC-area offices.

Category
People & HR (1)
Required Skills
Workday HRIS
Word/Pages/Docs
Excel/Numbers/Sheets
Requirements
  • Bachelor’s degree in Human Resources, Business Administration, or related field;
  • 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;
  • 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.
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.
Desired Qualifications
  • 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

YAi provides a quality control platform called ContentLift that evaluates and improves AI-generated text for marketing agencies and brands. The software works by automatically fact-checking claims against credible sources, adjusting tone to match a specific brand voice, and rewriting complex sentences for better readability. Unlike competitors that focus on generating new text, YAi acts as an independent assessment layer to ensure existing content is accurate and consistent. The company's goal is to create a repeatable process for organizations to produce high-quality, reliable content at scale.

Company Size

11-50

Company Stage

Seed

Total Funding

$330K

Headquarters

London, United Kingdom

Founded

2023

Simplify Jobs

Simplify's Take

What believers are saying

  • £250,000 SEIS funding from Jenson Ventures fuels product development in March 2025.
  • Audio and video capabilities launch in Q3 2025 for multimedia expansion.
  • Founders' exits from Yay!Starter and AI ventures enable rapid market penetration.

What critics are saying

  • OpenAI SearchGPT integrates fact-checking, obsoleting ContentLift in 6-12 months.
  • Anthropic Claude 3.5 embeds hallucination detection, undercutting core value in 6-9 months.
  • Copy.ai Agency Pro erodes market share with 40% lower pricing in 12-18 months.

What makes Yai unique

  • ContentLift evaluates and improves AI-generated content for brand voice and accuracy.
  • Proprietary framework scores originality, readability, and effectiveness automatically.
  • Optimizes content for AI search visibility and citations unlike generation tools.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Paid Vacation

Paid Sick Leave

401(k) Retirement Plan

401(k) Company Match

Life Insurance

Disability Insurance

Company News

YAi
Oct 1st, 2025
From Idea to Launch: Celebrating ContentLift's Product Hunt Debut

On September 17th, YAi introduced ContentLift to the world on Product Hunt, and the response blew YAi away.

YAi
May 27th, 2025
YAi makes BusinessCloud's MediaTech 50 ranking for 2025

YAi is proud to announce that YAi has been named one of the UK's most innovative media technology companies in the MediaTech 50 ranking for 2025, published today by BusinessCloud.

Tech.eu
Mar 12th, 2025
UK's YAi raises £250,000 for AI-driven content creation

UK AI content creation company YAi has raised £250,000 in Seed Enterprise Investment Scheme (SEIS) funding from Jenson Ventures.

Tech.eu
Mar 12th, 2025
YAi secures £250K for AI content

UK-based YAi has secured £250k in SEIS funding from Jenson Ventures to enhance its AI-driven content creation platform. Founded in 2023 by Yana Lapitskaya, Jessy Conflon, and Vyacheslav Lukin, YAi integrates AI content creation with real-time quality evaluation and automated improvement tools. The funding will aid in product development, team expansion, and market growth, with plans to add audio and video content capabilities in Q3.

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