Director, Legal - Litigation, PEO and Benefits

The Director, Legal – Litigation, PEO, and Benefits is a senior legal leader responsible for overseeing the organization’s litigation and claims portfolio and providing strategic guidance on disputes, investigations, and risk matters. This role also provides legal oversight and counsel for the company’s benefits, PEO, Paychex Insurance Agency, and captive insurance products and services.  

As a trusted advisor to senior leadership, the Director balances legal risk with business objectives across complex, highly regulated areas, including product, contracts, litigation, compliance, enterprise risk, and key business lines. The role requires exceptional judgment, strong leadership, and the ability to operate effectively in a fast-paced, high-volume environment. 

Litigation Strategy & Case Management 

• Lead the team responsible for litigation strategy, oversight, and resolution, including claims, disputes, arbitrations, and regulatory actions. 
• Manage complex, high-volume litigation portfolios across multiple jurisdictions. 
• Develop legal strategies that align with business priorities, risk tolerance, and financial considerations. 
• Partner with internal stakeholders to evaluate exposure and recommend resolution strategies, including settlement or trial. 
• Oversee and advise on claims, disputes, arbitrations, and litigation involving clients, vendors, and partners. 
• Represent and support the organization in regulatory hearings, investigations, trials, and audit responses. 
• Support matters involving FINRA, the SEC, insurance regulators, and PEO regulators. 

Product, Benefits, and Insurance Legal Support 

• Product and Service Support: Lead a team responsible for providing legal support for internal and external product areas, including retirement, health and benefits, COBRA, ACA, FSA/HRA/HSA, payroll, time and attendance, insurance, PEO, PIA, PSC, and related HR and administrative services. 
• Legal Guidance and Operations: Provide counsel on product development, implementation, claims, compliance, servicing, and operational matters. 
• New Initiatives and Integrations: Support new initiatives, product expansion, and product-related merger and acquisition integrations, including related legal implications. 
• Agreement Oversight: Manage the team responsible for drafting, reviewing, and negotiating agreements specific to benefit administration, insurance, and retirement plan agreements. 
• Support compliance matters involving licensing, collections, PEO, PSC, insurance, and related regulated business activities. 

Leadership and Team Development 

• Lead and oversee legal team performance: Supervise attorneys and legal staff to ensure high-quality, timely, and effective legal work across all matters by providing guidance, prioritization, and escalation support. 
• Review and guide legal strategy and work product: Provide oversight on case strategy, legal documents, and complex matters to ensure accuracy, consistency, and sound judgment. 
• Ensure compliance, ethics, and risk management: Maintain adherence to laws, regulations, and professional responsibility standards, minimizing legal and reputational risk.  
• Assign and manage workload across the team: Allocate cases and projects appropriately, monitor progress, and ensure deadlines and quality standards are met. 
• Coach, mentor, and develop attorneys: Support professional growth through feedback, training, and mentorship to build capability and leadership bench strength.  
• Serve as senior advisor to leadership and stakeholders: Provide strategic legal guidance to executives and business partners, aligning legal direction with organizational goals.  
• Drive operational excellence and team effectiveness: Establish processes, policies, and performance expectations to improve efficiency, consistency, and service delivery.  
• Manage escalated and high-risk legal matters: Direct or handle complex, sensitive, or high-impact issues requiring senior-level expertise and judgment. 
• Support recruiting, hiring, selection, and performance evaluation efforts to build and maintain a well-staffed, high-performing team. 

Required Qualifications 

• Juris Doctor (J.D.) from an accredited law school 
• Admitted to bar in a U.S. state and in good standing with the relevant bar association(s) in the US state(s) where licensed to practice law. 
• 15+ years of legal experience in private practice or a corporate legal department 
• Significant experience in advising sophisticated, publicly traded companies as to their litigation/claims portfolio and providing regulatory advice across a wide variety of matters, including tax, intellectual property, and risk matters. 
• Demonstrated executive presence, judgment, and business partnership skills. 
• Ability to manage complex, high-volume litigation matters across multiple stakeholders. 

Preferred Qualifications 

• Strong background in employee benefits, insurance, payroll, PEO, or other regulated services businesses. 
• Experience advising litigation matters in product-driven and highly regulated businesses. 
• Experience in benefits, insurance, PEO, PIA, payroll, or HR services legal support 
• Experience managing attorneys, outside counsel or legal support teams. 
• Prior in-house leadership experience 

• Act with uncompromising integrity.
• Provide outstanding service and build trusted relationships.
• Drive innovation in our products and services and continually improve our processes.
• Work in partnership and support each other.
• Be personally accountable and deliver on commitments.
• Treat each other with respect and dignity.
• What's in it for you?:
  • We value your well-being: We provide over 21 comprehensive rewards, including medical coverage, virtual wellness classes, tuition reimbursement, 401(k) + employer match, adoption assistance, financial assistance, and much more.
  • We value your time: From paid time off to company holidays, culture days, and comprehensive work-life balance programs, we will ensure you have the flexibility you need to be your best.
  • We value your development: Our award-winning training and development programs empower our employees with ongoing learning opportunities to give you the building blocks to grow your career.
  • We value your perspective: Our company culture reflects the diversity of our employees. We want you to be you and your voice to be heard.
  • We value our communities: We offer paid time off for volunteerism and promote many company-wide and local initiatives that benefit organizations you care about.
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    Note: The benefits described apply to full-time employees. Benefits for part-time, contract, and intern roles may vary. Not sure if you meet every requirement?: At Paychex, we know that great talent comes in many forms. If you're passionate about the role but don't check every box, we still encourage you to apply. You might be the right fit - either for this position or another opportunity with us.
    Paychex is an equal opportunity employer. We are committed to fostering a respectful and inclusive workplace where all individuals are treated fairly and evaluated based on their qualifications, experience, and merit. We comply with all applicable federal, state, and local laws prohibiting discrimination in employment.