Payroll Lead - (Multi-Entity)

We are seeking an experienced Payroll Lead (Multi-Entity) to own the end-to-end payroll process across our growing portfolio of companies. This is a hands-on payroll leadership role with a major initial objective: consolidate four separate weekly payrolls currently operating across four payroll systems into one standardized weekly payroll process on a single platform. This individual will own that project from evaluation and planning through conversion, testing, implementation, and stabilization. The Payroll Lead will work alongside our existing payroll specialists but will have a distinctly different responsibility. Our payroll specialists will continue working directly with drivers and employees, gathering payroll information, resolving day-to-day questions, and entering payroll data into the applicable systems. The Payroll Lead will own what happens next. Reviewing and validating payroll inputs, processing payroll, ensuring accuracy, reconciling results, maintaining appropriate controls, overseeing payroll tax compliance, and ultimately creating a consistent and scalable payroll process across all entities. The ideal candidate brings significant multi-entity and multi-state payroll experience, has personally worked through a payroll system conversion or consolidation, and is comfortable taking ownership of a complex payroll environment. Experience with transportation, logistics, trucking, or driver payroll is strongly preferred. Key Responsibilities Payroll Ownership

• Own the end-to-end weekly payroll process across multiple legal entities and states.
• Review and validate payroll information prepared and entered by payroll specialists before payroll is processed.
• Process and finalize weekly payroll, ensuring employees are paid accurately and on time.
• Own payroll controls, approvals, validation procedures, and exception reviews.
• Perform and own payroll reconciliations, identifying and resolving discrepancies before and after payroll processing.
• Ensure accurate treatment of earnings, deductions, reimbursements, bonuses, commissions, driver pay, and other variable compensation.
• Own federal, state, and local payroll tax compliance across all applicable jurisdictions.
• Ensure payroll processes comply with wage and hour requirements and applicable company policies.
• Own year-end payroll activities, including payroll reconciliations and W-2 accuracy.
• Maintain clear payroll procedures, controls, documentation, and audit trails.
• Partner with Accounting, Finance, HR, and Operations to ensure payroll is properly reflected in financial reporting and company records. Payroll Consolidation & Standardization A major priority for this position will be leading the transformation of our current payroll environment.
• Own the consolidation of four weekly payrolls operating across four separate payroll systems into one standardized weekly payroll process on a single platform.
• Develop and execute the payroll consolidation and conversion plan from beginning to end.
• Evaluate current payroll processes across each entity and identify differences, risks, inefficiencies, and opportunities for standardization.
• Establish standardized payroll procedures, controls, calendars, approval processes, and reporting across all entities.
• Own payroll data mapping, cleansing, validation, testing, and reconciliation throughout the conversion.
• Lead parallel payroll testing and confirm accuracy before transitioning entities to the consolidated platform.
• Coordinate with internal stakeholders and payroll-system partners throughout implementation.
• Establish a sustainable payroll operating model that can support additional entities and continued organizational growth.
• Identify opportunities for automation and process improvement after consolidation is complete. Required Qualifications
• 5+ years of progressive, hands-on payroll experience
• Significant experience processing and owning multi-entity payroll
• Strong multi-state payroll experience
• Hands-on experience with payroll system conversion, migration, implementation, or consolidation
• Experience owning payroll processing rather than solely preparing or entering payroll data
• Strong knowledge of federal, state, and local payroll regulations and payroll tax requirements
• Demonstrated experience with payroll reconciliations, controls, audits, and compliance
• Experience working with complex and/or variable compensation structures
• Strong Excel skills and ability to analyze and reconcile large payroll data sets
• Strong attention to detail and ability to maintain accuracy under weekly payroll deadlines
• Demonstrated ability to identify process gaps and establish standardized procedures
• Ability to independently take ownership of projects and drive them through completion
• Strong communication and cross-functional collaboration skills Preferred Qualifications
• Experience within transportation, trucking, logistics, freight, or a similar multi-location operational environment
• Experience with driver payroll or driver compensation
• Experience consolidating multiple companies, EINs, payroll systems, or payroll processes onto a common platform
• Experience supporting organizations with multiple business entities and varying compensation structures
• CPP or FPC certification is a plus What Success Looks Like Success in this role means creating a payroll operation that is accurate, controlled, consistent, and scalable. The Payroll Lead will successfully transition the organization from four separate weekly payrolls across four systems to one standardized weekly payroll process on one platform, without compromising payroll accuracy or continuity. Long term, this individual will own a payroll process with strong controls, accurate reconciliations, consistent procedures across entities, reliable tax compliance, and the infrastructure needed to support continued organizational growth. Background Check Employment is contingent upon successful completion of a background check in accordance with applicable federal, state, and local laws. Equal Employment Opportunity We are an Equal Opportunity Employer and are committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, national origin, age, disability, genetic information, veteran status, or any other characteristic protected by applicable federal, state, or local law.