Director of Payroll & Benefits

Director, Payroll & Benefits

Location: Virginia Beach, VA (Hybrid)

Reports to: VP of Human Resources

Direct Reports: Payroll & Benefits Specialist; potential oversight of HR Coordinator

Position Overview:

The Director of Payroll & Benefits is a key member of the HR leadership team, responsible for elevating and modernizing the company's payroll, benefits, and HRIS capabilities during a period of significant growth and organizational complexity. This role blends strategic leadership with hands-on operational excellence, ensuring accuracy, compliance, and a high-quality employee experience while preparing the organization for future expansion, including potential acquisitions and international integration.

This leader will serve as the company's primary payroll, benefits, and HRIS expert—capable of navigating complex employee situations, delivering strategic compensation insights to executives, and driving technology-enabled improvements, including emerging AI applications. The ideal candidate brings experience from larger, multi-state organizations and is energized by building scalable systems and processes for a growing enterprise.

Key Responsibilities:

Payroll Leadership & Operations

• Oversee end-to-end payroll operations for a multi-state, multi-entity workforce (1,150 U.S. employees; 150 Canada not yet integrated).
• Manage complex employee situations requiring business judgment beyond compliance.
• Lead payroll compliance across federal, state, and local jurisdictions.
• Develop and maintain scalable payroll processes, controls, and SOPs.
• Serve as the primary HRIS expert and system negotiator, currently Paycom, but experience with UKG or Workday is strongly preferred to bring fresh perspectives.
• Partner with Finance and Accounting on payroll reporting, reconciliations, audits, and bonus administration across multiple employee bands, including executive-level communication.
• Support capacity planning and workforce modeling as the company prepares for significant growth and potential acquisitions.

Benefits Strategy & Administration

• Lead the design, implementation, and management of comprehensive benefits programs (medical, dental, vision, life, disability, 401(k), HSA/FSA, voluntary benefits).
• Partner with HR leadership and external brokers to develop a forward-looking benefits strategy that balances cost, competitiveness, and employee experience.
• Guide the transition from a bundled benefits model to an unbundled TPA structure as the company scales.
• Oversee all compliance activities including plan testing, documentation, and required filings.
• Manage vendor relationships to ensure high-quality service delivery and plan performance.
• Monitor and analyze benefits spend and utilization, providing insights and recommendations to leadership.

Open Enrollment & Employee Experience

• Lead annual open enrollment strategy, including plan design, cost modeling, decision support, and execution.
• Develop multi-channel communication strategies to enhance employee understanding and engagement.
• Implement feedback loops (surveys, engagement tools) to continuously improve offerings and communication.

Systems, Data & AI-Driven Improvement

• Leverage HR technology and emerging tools, including AI, to enhance payroll and benefits processes, reporting, and decision-making.
• Support the company's AI rollout (Claude desktop for directors and plant managers) within established governance frameworks.
• Drive data-informed insights across compensation, benefits utilization, and payroll trends.
• Identify and implement process improvements that increase efficiency, accuracy, and scalability.

Leadership & Collaboration

• Lead, develop, and mentor payroll and benefits team members, fostering a culture of accountability and continuous improvement.
• Collaborate cross-functionally with HR, Finance, and business leaders to align programs with organizational goals.
• Play a key role in future growth initiatives, including anticipated acquisitions of 500–1,000 employees within 18–24 months.
• Operate with a practical, business-focused approach aligned with company culture.

Qualifications

Education & Experience

• Bachelor's degree in Business, HR, Finance, or related field preferred.
• 7+ years of progressive experience in payroll, benefits, or total rewards.
• Strong experience managing multi-state payroll operations; multi-entity experience preferred.
• Leadership experience with direct reports.
• Experience in larger organizations (500–1,000+ employees) strongly preferred.
• Exposure to international payroll/benefits (Canada) a plus.
• CPP, SHRM, or CEBS certification preferred.

Skills & Capabilities

• Strategic mindset with the ability to execute at a detailed operational level.
• Strong analytical skills with a data-driven approach to decision-making.
• Experience with advanced HRIS platforms
• Interest in and openness to expanding AI capabilities.
• Excellent communication and executive-level presentation skills.
• High integrity and ability to manage confidential information.
• Proactive, solutions-oriented, and comfortable in a fast-paced, growth-oriented environment.

Work Environment & Additional Information

• Hybrid work environment based in Virginia Beach.
• Onsite expectation: 2–3 days/week initially for training and relationship building; transitions to 1 day/week after 6 months.
• Minimal travel (up to 10%).