Director of Benefits (New York City Metropolitan Area)

Our client’s law firm is seeking an experienced Director of Benefits, Retirement & Risk Management to lead the administration, strategy, compliance, and ongoing management of the Firm’s employee benefits, retirement plans, leave and disability programs, and property and casualty insurance.

This position combines strategic oversight with hands-on operational responsibility. The Director will serve as a subject matter expert and primary resource for benefits, retirement, insurance, compliance, and vendor management. The role will work closely with Firm leadership, partners, attorneys, business professionals, employees, Human Resources, Finance, Payroll, Information Technology, brokers, actuaries, auditors, recordkeepers, legal counsel, carriers, and other external partners.

The ideal candidate is comfortable operating at both a strategic and detailed level—advising senior leaders, resolving complex employee and participant matters, reviewing plan and financial data, supporting audits and regulatory filings, managing renewals and claims, and holding vendors accountable for timely and accurate deliverables. This is a hands-on leadership position where the Director will maintain direct ownership of critical processes and escalations.

JOB RESPONSIBILITIES

Partner & Leadership Advisory

• Serve as a trusted resource to Firm leadership and partners regarding employee benefits, retirement programs, insurance coverage, and associated risks.
• Interpret complex benefits, actuarial, insurance, financial, and regulatory information and translate it into practical recommendations.
• Prepare clear analyses, reports, and presentations for the COO, Firm leadership, and relevant committees.
• Handle sensitive and confidential matters with professionalism, discretion, sound judgment, and a strong service orientation.

Health & Welfare Benefits

• Oversee the Firm’s medical, dental, vision, life, short- and long-term disability, voluntary benefits, wellness, and related programs.
• Act as the primary escalation point for complex eligibility, coverage, claims, service, and employee or partner benefit matters.
• Lead annual open enrollment, including planning, system preparation, implementation, communications, employee education, and post-enrollment reconciliation.
• Evaluate plan design, competitiveness, utilization, costs, employee experience, and service levels, recommending improvements as appropriate.
• Develop clear and targeted benefits communications for partners, attorneys, business professionals, employees, and committees.

Retirement Plans

• Oversee the administration and governance of the Firm’s 401(k), profit-sharing, and cash balance plans.
• Coordinate annual audits, compliance testing, actuarial activities, funding requirements, government filings, and Form 5500 preparation.
• Support Investment Committee and fiduciary activities through meeting preparation, documentation, record maintenance, and action-item follow-up.
• Manage relationships with recordkeepers, actuaries, auditors, ERISA counsel, Payroll, Finance, and other stakeholders.
• Review and reconcile eligibility, census, compensation, contributions, allocations, funding, and participant data, investigating and correcting discrepancies.
• Address participant questions and escalations and communicate plan provisions and annual processes clearly.
• Monitor regulatory and legislative changes and coordinate necessary plan or administrative updates.

Leaves, Disability & Accommodations

• Oversee leave administration, including FMLA, New York Paid Family Leave, short- and long-term disability, workers’ compensation, and other applicable leave programs.
• Coordinate complex leave, disability, accommodation, benefits-continuation, and return-to-work matters with HR, Payroll, vendors, and legal counsel.
• Monitor documentation, payroll coordination, benefit deductions, provider performance, and employee communications.
• Serve as a senior escalation resource for sensitive and complex leave or disability matters.

Property, Casualty & Risk Management

• Manage relationships with the Firm’s property and casualty insurance brokers and carriers.
• Lead annual insurance renewals, including coverage reviews, applications, exposure information, benchmarking, negotiations, binding, and renewal recommendations.
• Coordinate claims activity, documentation, and communications among brokers, carriers, adjusters, counsel, Facilities, IT, Finance, and other stakeholders.
• Oversee or coordinate property, general liability, cyber, employment practices liability, fiduciary liability, crime, umbrella/excess liability, and workers’ compensation coverage.
• Coordinate with Firm leadership regarding professional liability insurance administration and renewals.
• Maintain accurate policy, renewal, claims, and coverage documentation and ensure outstanding issues are tracked through resolution.

Financial Management, Reporting & Reconciliation

• Develop and manage annual benefits and insurance budgets, forecasts, cost projections, and renewal analyses.
• Partner with Finance, Payroll, and external providers to review invoices, funding requirements, deductions, employer contributions, plan expenses, and related financial activity.
• Conduct regular reconciliations of benefit deductions, eligibility, carrier invoices, participant information, retirement contributions, and plan funding, personally addressing significant discrepancies.
• Provide benefits, retirement, leave, and insurance data needed for accounting, audits, regulatory reporting, financial analysis, and management reporting.
• Establish and monitor key metrics related to costs, utilization, participation, service levels, employee inquiries, claims, operational accuracy, and vendor performance.

Compliance, Governance & Documentation

• Ensure compliance with ERISA, ACA, COBRA, HIPAA, FMLA, ADA, Section 125, Medicare, Social Security, Department of Labor requirements, and applicable federal, state, and local regulations.
• Coordinate required benefits and retirement reporting and filings, including Form 5500, ACA reporting, prescription drug data reporting, and other applicable filings.
• Maintain current plan documents, SPDs, SMMs, annual notices, policies, committee records, insurance policies, and other governance documentation.
• Maintain documented procedures, annual calendars, vendor contacts, renewal schedules, audit files, controls, and responsibility matrices.
• Review employee communications and administrative practices to ensure consistency with plan documents, policies, and vendor administration.
• Identify and mitigate operational, compliance, fiduciary, and control risks and ensure issues are resolved appropriately.

Vendor, Broker & Technology Management

• Serve as the primary relationship owner for benefits and insurance brokers, recordkeepers, actuaries, auditors, carriers, counsel, third-party administrators, technology providers, and other vendors.
• Lead or support vendor selection, RFP/RFI processes, contract and fee negotiations, implementations, renewals, and transitions.
• Establish service expectations and conduct regular vendor performance reviews focused on responsiveness, accuracy, cost, compliance, participant service, and overall value.
• Hold vendors accountable for errors, missed deadlines, incomplete deliverables, and unresolved employee, participant, or claims matters.
• Oversee benefits-related system configuration, data integrity, reporting, eligibility interfaces, and vendor feeds within HRIS, payroll, and benefits platforms.
• Partner with HR, Payroll, Finance, IT, and vendors to test system changes, resolve data issues, strengthen controls, and automate recurring processes where appropriate.

Team Leadership & Hands-On Execution

• Lead, develop, and establish accountability for team members supporting benefits, retirement, leave, and insurance functions.
• Assign and review work, provide coaching and feedback, and manage performance.
• Establish clear responsibilities, backup coverage, cross-training, and documented procedures to ensure operational continuity.
• Remain directly involved in critical reconciliations, audits, filings, renewals, claims, escalations, documentation, and follow-up while effectively delegating responsibilities.
• Manage competing priorities and deadlines, proactively communicate risks or capacity concerns, and ensure work is completed accurately and on schedule.
• Promote a collaborative, responsive, service-focused, and continuous-improvement culture.

QUALIFICATIONS

Required

• Bachelor’s degree with 10+ years of progressive employee benefits experience, including leadership responsibilities.
• Extensive experience administering and governing 401(k), profit-sharing, cash balance, or other defined benefit plans.
• Hands-on knowledge of retirement plan audits, Form 5500 filings, compliance testing, plan data, participant matters, and fiduciary or investment committee support.
• Strong understanding of health and welfare programs, including medical, dental, vision, life, disability, leave, and related compliance requirements.
• Excellent communication, presentation, analytical, organizational, and project management skills.
• Strong executive presence and the ability to establish credibility with partners, attorneys, senior leadership, employees,]]>