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.

Key Responsibilities:

Payroll Processing & Administration

• 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.

Payroll Calculation & Compliance

• Accurately calculate and validate wages, overtime, shift differentials, bonuses, commissions, retro pay adjustments, deductions, garnishments, and benefit withholdings.

• Ensure full compliance with all federal, state, and local payroll tax regulations as well as 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.

Payroll Reconciliation & Reporting

• 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.

Employee Support & Cross Functional Collaboration

• 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.

Process Improvement & Systems Implementation

• 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.

Qualifications:

• 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 within 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