Driver Payroll Specialist - Transportation & Logistics - Winter Haven, FL

Job Title: Driver Payroll Specialist

Department: Payroll / Accounting
Reports To: Payroll Manager
Location: Winter Haven, FL (On-site)
Job Type: Full-Time

Position Summary

Indian River Transport is seeking a detail-oriented Driver Payroll Specialist to manage end-to-end payroll processing for our driver population and support payroll-related accounting, reconciliations, and driver inquiries. This role requires deep familiarity with driver pay structures (CPM, per diem, detention, layover, bonuses, advances), excellent Excel skills, and experience working with payroll systems and transportation/TMS platforms. The Driver Payroll Specialist will ensure accurate, timely payrolls and payroll accounting while protecting confidential employee/pay data.

Essential Duties & Responsibilities

• Process driver payrolls (weekly) from source systems and settlements through to final pay: calculate loaded/empty CPM, per diem, layover, detention, bonuses, advances, incentive pay and miscellaneous adjustments.
• Apply and track payroll deductions: taxes, benefits, wage garnishments, loan/advance paybacks, and voluntary deductions.
• Reconcile driver settlements and payroll registers to general ledger and produce journal entries for posting.
• Maintain and audit driver pay files and settlement records; research and resolve discrepancies between settlements, TMS/settlement system, and payroll outputs.
• Serve as primary payroll point of contact for drivers: respond to pay questions, explain statements/adjustments, and resolve disputes professionally and promptly.
• Partner closely with Operations/Dispatch to validate pay-affecting data (miles, loads, layovers, detentions, off-route miles, ELD/HOS exceptions) prior to payroll cut-off.
• Maintain payroll process documentation, internal controls, and audit-ready files; assist with internal and external payroll audits.
• Perform ad-hoc payroll and finance projects as assigned (system integrations, process improvements, automation initiatives).
• Ensure strict confidentiality and security of payroll data and compliance with federal, state, and local payroll laws (including FLSA and state wage requirements).

Qualifications

• 2–4 years payroll/accounting experience; prior experience with driver payroll or transportation payroll strongly preferred.
• Working knowledge of payroll processing, tax and deduction mechanics, garnishments, benefits withholding, and payroll best practices.
• Comfortable with driver pay constructs (CPM, per diem, layover/detention pay, settlements); able to translate operational inputs into payroll outcomes.
• Strong Excel skills (pivot tables, lookups, formulas) and experience with payroll/ERP systems. Experience with AS400/Innovative, TMS, ADP/Paychex or similar preferred.
• High attention to detail, strong analytical skills, and ability to reconcile high-volume transactional data accurately.
• Excellent verbal and written communication skills; ability to explain pay details clearly to drivers and managers.
• Demonstrated integrity and ability to handle confidential information with care.
• Associate’s or Bachelor’s degree in Accounting, Finance, HR, or related field preferred but not required. Payroll certification (CPP) a plus.
• Valid driver’s license required; CDL not required.

Skills & Tools

• Payroll systems / PEO interface experience (ADP, Paychex, or equivalent)
• Fleet/TMS or settlement system familiarity (AS400 preferred)
• Strong organizational skills and ability to meet strict payroll deadlines

Work Environment & Schedule

• On-site at Winter Haven terminal; standard business hours with occasional extended hours required during payroll cutoffs or month-end.
• Fast-paced environment with frequent interaction with Operations, HR, Safety, and Finance teams.

Performance Measures (examples)

• Payroll accuracy rate (errors per pay cycle)
• Timeliness of payroll processing and GL reconciliation completion
• Average time to resolve driver pay inquiries
• Audit findings and control compliance metrics

Benefits

• Standard company benefits package: 401(k) with match, health/dental/vision, life insurance, paid time off, and opportunities for professional development.

Indian River Transport is an Equal Opportunity Employer. We value diversity and are committed to building an inclusive workplace.

Call-To-Action

If you're ready to take your career to the next level with a company that values integrity and growth, we invite you to apply today and become part of our dedicated team! Please submit your resume and a brief cover note highlighting payroll and transportation-related experience to: HR@IndianRiverTransport.com. Use subject line: Driver Payroll Specialist — Winter Haven.

Job Type: Full-time

Benefits:

• 401(k) matching
• Dental insurance
• Employee assistance program
• Employee discount
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Vision insurance

Application Question(s):

• Please describe your experience as it relates to the position.

Experience:

• Payroll or Accounting: 2 years (Required)
• Driver Payroll: 1 year (Preferred)
• Transportation management systems: 1 year (Preferred)
• AS400: 1 year (Preferred)

Ability to Commute:

• Winter Haven, FL 33884 (Required)

Work Location: In person