Director of , Retirement & Risk Mgmt

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Regular Full-Time Management NEW YORK, NY, US

Salary Range: $ To $ Annually

JOB SUMMARY

Pryor Cashman LLP is 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 requires both strategic leadership and 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 and will work closely with Firm leadership, partners, attorneys, business professionals, employees, Finance, Payroll, Human Resources, Information Technology, brokers, actuaries, auditors, recordkeepers, counsel, carriers, and other providers.

The ideal candidate is equally comfortable advising partners and Firm leadership, resolving employee and participant issues, reviewing and reconciling plan data, assembling audit and filing support, coordinating renewals and claims, and driving vendor deliverables to completion. Because the Firm operates with streamlined teams, this is not a role limited to strategy or oversight. The Director must be willing to work directly through operational details and assume personal ownership of critical processes and escalations.

JOB RESPONSIBILITIES

• Serve as a trusted adviser to partners and Firm leadership on benefits, retirement plans, insurance, and related risks.
• Translate technical plan, actuarial, insurance, financial, and compliance information into clear, practical guidance and 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 strong client‑service orientation.

• 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, communications, employee education, and post‑enrollment reconciliation.
• Evaluate plan competitiveness, utilization, cost, employee experience, and service performance and recommend plan or process changes.
• Develop clear, accurate, and audience‑appropriate communications for partners, attorneys, business professionals, employees, and committees.

• Lead 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 preparation of meeting materials, maintenance of records, and follow‑up on action items.
• 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.
• Resolve participant issues and escalations and develop clear partner and participant communications regarding plan provisions and annual…