Payroll Specialist

Chesapeake Search Partners has been engaged by a growing transportation and logistics company to identify a Payroll Specialist for their organization. The Payroll Specialist will oversee and manage all aspects of payroll processing for their large, multi-state workforce. This individual will serve as the sole payroll professional for the organization and will play a critical role in ensuring accurate and timely payroll processing across a diverse employee population that includes salaried, hourly, union, and 1099 employees.

• Process weekly and bi-weekly payroll for hundreds of employees across multiple pay groups, ensuring timely and accurate payroll submission in accordance with internal deadlines.
• Manage end-to-end payroll administration for salaried, hourly, union, and independent contractor (1099) employees across multiple business units and job classifications.
• Maintain and update employee payroll records, ensuring accuracy of compensation, tax elections, direct deposit information, and other payroll-related data while maintaining strict confidentiality.

• Accurately calculate and validate wages, overtime, shift differentials, bonuses, commissions, retro pay adjustments, deductions, garnishments, and benefit with holdings.
• Ensure full compliance with all federal, state, and local payroll tax regulations and applicable union agreements, including wage rates, benefit contributions, and reporting requirements.
• Coordinate payroll tax filings and remittances, and oversee year-end reporting processes including W-2s, 1099s, and other required regulatory filings.

• Reconcile payroll prior to and post-processing, including balancing payroll registers, general ledger interfaces, tax filings, and benefit deductions.
• Assist with reporting and data analysis related to labor costs, payroll trends, and headcount to support financial planning and operational decision-making.
• Support internal and external audits by preparing documentation, responding to audit requests, and ensuring payroll records are accurate, complete, and readily available.

• Serve as the primary point of contact for employee payroll inquiries, resolving discrepancies and providing timely, professional support to employees and internal stakeholders.
• Partner closely with HR, Finance, Operations, and Safety teams to ensure accurate onboarding, job changes, pay adjustments, and proper system integration across all employee data.

• Identify and implement opportunities to improve payroll processes, enhance controls, and standardize procedures to increase efficiency, accuracy, and compliance.
• Support leadership in the centralization, modernization, and optimization of payroll systems and workflows, including potential system upgrades or process automation initiatives.

• 3+ years of payroll processing experience, preferably in a high-volume environment
• Experience processing payroll for union employees strongly preferred
• Strong understanding of payroll laws, tax regulations, and compliance requirements
• Experience handling multi-state payroll preferred
• Proficiency in payroll systems and Microsoft Excel
• Strong attention to detail and organizational skills
• Ability to work independently and manage competing priorities
• Excellent communication and problem-solving abilities
• Experience with in transportation, logistics, manufacturing, or other operationally driven industries is a plus
• CPP certification is a plus but not required
• Discretion and professionalism in handling confidential payroll matters