Director of Benefits & HR Compliance

Director of Benefits & HR Compliance

Executive HR Leadership | Elite AmLaw Firm

📍 Location Options: Washington, DC • New York, NY • Chicago, IL

🏢 Hybrid Schedule: Tuesday–Thursday in-office

💰 $250,000–$280,000 Annual Bonus (Higher compensation may be considered for exceptional candidates.)

The best HR leaders don't simply administer benefits. They shape the employee experience, influence executive decision-making, control millions in healthcare spend, and build the infrastructure that attracts and retains world-class talent.

Plona Partners has been retained to identify a Director of Benefits & HR Compliance for a prestigious AmLaw firm recognized as one of the nation's most respected legal organizations. While we're keeping the firm's identity confidential during the early stages of the search, this is a rare executive-level opportunity to lead enterprise-wide benefits strategy, HR compliance, and total rewards for a sophisticated, national workforce. If you're passionate about designing competitive benefits programs, advising executive leadership, driving operational excellence, and influencing firm-wide people strategy, this is the kind of opportunity that can define your career.

The Opportunity

Reporting to senior Human Resources leadership, you'll oversee the firm's entire Benefits and HR Compliance function while serving as a trusted advisor to executive leadership on workforce strategy, employee experience, healthcare costs, regulatory compliance, and total rewards.

This is far more than a traditional benefits role.

You'll lead strategic initiatives that directly impact recruitment, retention, financial performance, and employee well-being across one of the country's premier law firms.

What You'll Be Doing

• Develop and execute the firm's enterprise-wide benefits strategy, including health & welfare, retirement, leave, and wellness programs

• Advise executive leadership on benefits trends, workforce planning, and total rewards initiatives that strengthen talent acquisition and retention

• Lead HR compliance strategy by overseeing policies, governance, regulatory compliance, and internal controls

• Manage multimillion-dollar healthcare programs through analytics, vendor management, and innovative plan design

• Oversee retirement plans, including 401(k), pension, and partner retirement programs

• Ensure compliance with ERISA, ACA, HIPAA, COBRA, FMLA, IRS regulations, Section 125, Form 5500, and applicable federal, state, and local laws

• Lead vendor relationships, broker negotiations, RFPs, renewals, and contract management to maximize value and service

• Drive employee communications and open enrollment strategies that improve participation and understanding

• Leverage analytics, utilization trends, benchmarking, and employee feedback to continuously improve program effectiveness

• Partner with Finance, Payroll, Legal, IT, HR leadership, and firm management on strategic people initiatives

• Lead, mentor, and develop a high-performing Benefits team while fostering collaboration across the broader HR organization

Why This Opportunity Stands Out

✔ Executive leadership role within one of the nation's premier law firms

✔ Direct influence over firm-wide talent strategy, employee experience, and organizational performance

✔ Opportunity to modernize benefits, improve operational efficiency, and shape long-term HR strategy

✔ Significant visibility with executive leadership and key business stakeholders

✔ Hybrid work schedule with flexibility

✔ Outstanding compensation, bonus potential, and long-term career growth

We're Looking For

• 10 years of progressive Human Resources leadership experience

• 5 years leading and developing HR or Benefits teams

• Deep expertise designing and administering complex health, welfare, retirement, leave, and well-being programs

• Strong working knowledge of ERISA, ACA, HIPAA, COBRA, FMLA, IRS regulations, Section 125, Form 5500, and related compliance requirements

• Experience managing healthcare costs, vendor negotiations, benefits analytics, and operational strategy

• Proven success developing HR policies, governance frameworks, and compliance programs

• Strong executive presence with the ability to influence senior leadership and cross-functional stakeholders

• Experience leading organizational change, process improvements, and strategic HR initiatives

• Law firm or other professional services experience is highly preferred