Director of Benefits, Retirement & Risk Mgmt

PRYOR CASHMAN•New York, NY

3h•$190,000 - $225,000•Hybrid

About The Position

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.

Requirements

Bachelor’s degree and 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 build credibility with partners, attorneys, senior leaders, 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 complex data, reconcile information from multiple sources, and convert findings into practical recommendations.
Demonstrated discretion in handling highly confidential partner, employee, health, claims, compensation, and retirement information.
Ability to operate effectively under pressure, manage competing deadlines, and move fluidly between strategic advice and detailed execution.
Direct supervisory or team-leadership experience.

Nice To Haves

Law firm or professional services experience.
Experience managing property and casualty insurance relationships, renewals, and claims.
Experience operating in 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.

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 processes.
Monitor relevant legislative and regulatory developments and coordinate required plan or administrative changes.
Oversee administration of leaves of absence, including FMLA, New York Paid Family Leave, short-term disability, long-term disability, workers’ compensation, and other applicable federal, state, and local leave programs.
Coordinate complex leave, disability, benefits-continuation, accommodation, and return-to-work matters with Human Resources, Payroll, providers, and counsel, as appropriate.
Monitor leave documentation, payroll coordination, benefit deductions, provider performance, and employee communications.
Serve as an escalation point for complex or sensitive leave and disability matters.
Manage the Firm’s property and casualty insurance broker and carrier relationships.
Oversee annual renewals, policy and coverage reviews, applications, exposure data, insurance schedules, marketing, benchmarking, negotiations, binding, and renewal recommendations.
Coordinate claims reporting and support, including document collection and communications with brokers, carriers, adjusters, counsel, facilities, Information Technology, Finance, and other internal stakeholders.
Oversee or coordinate coverages such as property, general liability, cyber, employment practices liability, fiduciary liability, crime, umbrella or excess liability, and workers’ compensation.
Coordinate with the appropriate Firm leaders on professional liability insurance administration and renewals.
Maintain organized policy, renewal, claims, and coverage records and track open items through resolution.
Develop and manage annual benefits and insurance budgets, forecasts, cost projections, and renewal analyses.
Partner with Finance, Payroll, and outside 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 required for accounting, financial reporting, audits, regulatory filings, and management analysis.
Establish and monitor meaningful metrics, including cost, utilization, participation, service performance, employee inquiries, claims trends, operational accuracy, and vendor performance.
Maintain compliance with ERISA, ACA, COBRA, HIPAA, FMLA, ADA, Section 125, Medicare, Social Security, Department of Labor requirements, and other applicable federal, state, and local requirements.
Coordinate required benefits and retirement reporting and filings, including Form 5500, ACA reporting, prescription drug data reporting, and other applicable requirements.
Maintain current plan documents, summary plan descriptions, summaries of material modifications, policies, annual notices, committee records, insurance policies, and related governance materials.
Maintain written procedures, annual calendars, vendor contacts, renewal schedules, audit support files, controls, and responsibility matrices to support continuity and cross-training.
Review employee-facing materials and administrative practices for consistency with governing plan documents, policies, and provider administration.
Identify operational, compliance, fiduciary, and control risks and drive issues to resolution with appropriate advisers and stakeholders.
Serve as the accountable relationship owner for benefits and insurance brokers, recordkeepers, actuaries, auditors, carriers, counsel, third-party administrators, technology providers, and other service providers.
Lead or coordinate vendor selection, RFP and RFI processes, contract and fee negotiations, implementations, renewals, and transitions.
Establish service expectations and conduct periodic performance reviews 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 Human Resources, Payroll, Finance, Information Technology, and vendors to test system changes, resolve data issues, improve controls, and automate recurring processes where practical.
Directly supervise, develop, and establish clear accountability for benefits team members and other employees supporting benefits, retirement, leave, and insurance processes, including assigning and reviewing work, providing feedback, and managing performance.
Establish clear roles, effective back-up coverage, cross-training, and written procedures to ensure continuity and appropriate staffing within a streamlined team.
Remain personally involved in critical operational work, reconciliations, audits, filings, escalations, renewals, claims, documentation, and follow-up while delegating effectively and developing team members.
Manage competing priorities and deadlines, communicate capacity constraints and risks early, and ensure responsibilities are completed accurately and on time.
Foster a collaborative, responsive, service-oriented, and continuous-improvement culture.