Director of Benefits, Retirement & Risk

Position: Director of Benefits, Retirement & Risk Management

Department: Administration

Salary: $190,000 - $250,000

Onsite Logistics: Hybrid – 3 days onsite

Hours: Monday–Friday, 9:30am–5:30pm

Status: Exempt

Reports To: Chief Operating Officer

Position Summary

Seeking an experienced, hands-on Director of Benefits, Retirement & Risk Management to oversee the firm’s employee benefits programs, retirement plans, leaves and disability programs, property and casualty insurance relationships, and related compliance and governance activities.

This role combines strategic leadership with significant day-to-day execution. The Director will serve as the firm’s primary subject matter expert for benefits, retirement programs, insurance coverage, and vendor management, working closely with firm leadership, partners, attorneys, business professionals, employees, Finance, Payroll, Human Resources, Information Technology, and external providers.

The successful candidate must be comfortable moving between executive-level advisory responsibilities and detailed operational execution. This is not a strategy-only leadership role; the Director will remain personally involved in critical processes, reconciliations, audits, filings, renewals, claims, escalations, and vendor follow-up.

Responsibilities:

Partner & Leadership Advisory

• Serve as a trusted adviser to partners and firm leadership regarding employee benefits, retirement plans, insurance coverage, and related risks.
• Translate complex plan, actuarial, insurance, financial, and compliance information into clear and practical recommendations.
• Prepare concise, decision-oriented analyses and presentations for the Chief Operating Officer, firm leadership, and applicable committees.
• Handle sensitive, disputed, and confidential matters with discretion, sound judgment, composure, and a strong client-service orientation.

Health & Welfare Benefits

• Oversee the firm’s medical, dental, vision, life, short-term disability, long-term disability, voluntary benefits, wellness, and related health and welfare programs.
• Serve as the principal escalation point for complex partner, attorney, employee, eligibility, coverage, claims, and service issues.
• Lead annual open enrollment strategy, system readiness, implementation, employee communications and education, and post-enrollment reconciliation.
• Evaluate plan competitiveness, utilization, cost, employee experience, and vendor service performance and recommend appropriate plan or process changes.
• Develop clear and accurate benefits communications for partners, attorneys, business professionals, employees, and firm committees.

Retirement Plans

• Lead the administration and governance of the firm’s 401(k), profit sharing, and cash balance plans .
• Coordinate annual plan audits, compliance testing, actuarial work, funding requirements, government filings, and Form 5500 preparation and filing.
• Support the Investment Committee and other fiduciary governance processes, including meeting preparation, record maintenance, and action-item follow-up.
• Coordinate with recordkeepers, actuaries, auditors, ERISA counsel, Payroll, Finance, and other internal and external stakeholders.
• Review and reconcile census, eligibility, compensation, contribution, allocation, funding, and participant data.
• Investigate discrepancies and drive corrections through completion.
• Resolve participant issues and escalations and prepare clear communications regarding plan provisions and annual processes.
• Monitor legislative and regulatory developments and coordinate required plan or administrative changes.

Leaves, Disability & Accommodations

• Oversee administration of leaves of absence, including FMLA, New York Paid Family Leave, short-term disability, long-term disability, workers’ compensation, and other applicable leave programs.
• Coordinate complex leave, disability, benefits-continuation, accommodation, and return-to-work matters with Human Resources, Payroll, providers, and counsel.
• Monitor leave documentation, payroll coordination, benefit deductions, provider performance, and employee communications.
• Serve as the escalation point for complex or sensitive leave and disability matters.

Property, Casualty & Risk Management

• Manage the firm’s property and casualty insurance broker and carrier relationships.
• Oversee annual insurance renewals, policy and coverage reviews, applications, exposure data, insurance schedules, benchmarking, negotiations, binding, and renewal recommendations.
• Coordinate claims reporting and support with brokers, carriers, adjusters, counsel, Facilities, IT, Finance, and other internal stakeholders.
• Oversee or coordinate property, general liability, cyber, employment practices liability, fiduciary liability, crime, umbrella/excess liability, and workers’ compensation coverage.
• Coordinate with appropriate firm leadership regarding professional liability insurance administration and renewals.
• Maintain organized policy, renewal, claims, and coverage records and track open matters 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, employee deductions, employer contributions, plan expenses, and related financial activity.
• Oversee periodic reconciliation of benefit deductions, eligibility, carrier invoices, participant data, retirement contributions, and plan funding.
• Personally investigate and resolve material discrepancies.
• Provide benefits, retirement, leave, and insurance data needed for financial reporting, audits, regulatory filings, and management analysis.
• Establish and monitor metrics related to cost, utilization, participation, service performance, claims trends, operational accuracy, and vendor performance.

Compliance & Governance

• Maintain compliance with ERISA, ACA, COBRA, HIPAA, FMLA, ADA, Section 125, Medicare, Social Security, Department of Labor requirements, and other applicable regulations.
• Coordinate required benefits and retirement reporting and filings, including Form 5500, ACA reporting, and prescription drug data reporting.
• Maintain current plan documents, SPDs, summaries of material modifications, policies, annual notices, committee records, insurance policies, and related governance documentation.
• Maintain written procedures, annual calendars, renewal schedules, audit-support files, controls, and responsibility matrices.
• Identify operational, compliance, fiduciary, and control risks and drive issues to resolution with appropriate advisers and stakeholders.

Vendor, Broker & Technology Management

• Serve as the primary relationship owner for benefits and insurance brokers, recordkeepers, actuaries, auditors, carriers, counsel, third-party administrators, and technology providers.
• Lead or coordinate vendor selection, RFP/RFI processes, fee and contract negotiations, implementations, renewals, and transitions.
• Establish service expectations and evaluate vendor performance based on responsiveness, accuracy, cost, participant service, compliance, and strategic value.
• Hold providers accountable for errors, missed deadlines, incomplete work, and unresolved participant or claims issues.
• Oversee benefits-related configuration, data integrity, reporting, eligibility interfaces, and vendor feeds within the firm’s HRIS, payroll, and benefits-administration systems.
• 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

• Directly supervise and develop employees supporting benefits, retirement, leave, and insurance processes.
• Assign and review work, provide feedback, establish clear accountability, and manage performance.
• Establish appropriate backup coverage, cross-training, and written procedures to support continuity within a streamlined team.
• Remain personally involved in critical operational work, reconciliations, audits, filings, escalations, renewals, claims, documentation, and follow-up.
• Manage competing priorities and deadlines while communicating capacity constraints and risks proactively.
• Foster a collaborative, responsive, service-oriented, and continuous-improvement culture.

Qualifications

Required

• Bachelor’s degree required.
• At least 10 years of progressive employee benefits experience , including leadership responsibility.
• Demonstrated experience administering and governing 401(k), profit sharing, and cash balance or other defined benefit plans .
• Hands-on experience with retirement plan audits, Form 5500 filings, compliance testing, plan data, participant issues, and fiduciary or investment committee support.
• Strong knowledge of health and welfare plans, including medical, dental, vision, life, disability, leave, and related compliance requirements.
• Excellent written and verbal communication, presentation, analytical, organizational, and project-management skills.
• Demonstrated executive presence and ability to establish credibility with partners, attorneys, senior leadership, employees, and external advisers.
• Proven success managing brokers, carriers, vendors, auditors, actuaries, recordkeepers, counsel, and other outside providers.
• Advanced attention to detail and the ability to analyze and reconcile complex information from multiple sources.
• Ability to translate detailed findings into practical business recommendations.
• Demonstrated discretion when handling highly confidential partner, employee, health, claims, compensation, and retirement information.
• Ability to operate effectively under pressure and move fluidly between strategic advisory responsibilities and detailed execution.
• Direct supervisory or team-leadership experience.

Preferred

• Law firm or professional-services experience.
• Experience managing property and casualty insurance relationships, renewals, and claims.
• Experience operating within a streamlined organization with limited administrative layers.
• Experience with ADP Workforce Now or comparable HRIS, payroll, and benefits-administration platforms.
• Experience with benefits analytics, financial forecasting, and vendor-selection processes.
• Professional certification such as CEBS, SPHR, or a comparable credential.