Controller, Accounting & Fleet Finance

USA Logistics Inc is seeking a Controller, Accounting & Fleet Finance to lead full-cycle accounting and fleet finance for an onsite team in Woodridge, IL. This role focuses on improving settlement accuracy, strengthening controls, and increasing visibility into cash flow and profitability, with close coordination between in-house accounting and an offshore team supporting load creation and TMS data hygiene.

You will build scalable processes across the general ledger, driver and vendor accounting, truck-level tracking, and monthly reporting, while ensuring documentation and audit trails are complete and reliable.

What you’ll do

• Manage, coach, and develop two Driver/Vendor Accounting team members and one Finance Associate.
• Set clear responsibilities, workflows, deadlines, review procedures, and performance expectations.
• Oversee daily accounting operations to ensure accurate, timely records.
• Review reconciliations, settlement exceptions, vendor balances, journal entries, and other material transactions.
• Own the company’s general ledger, chart of accounts, and full-cycle bookkeeping.
• Ensure revenue, expenses, accruals, debt obligations, and other transactions are recorded accurately in the correct accounting periods.
• Run the monthly close, prepare monthly financial statements (income statement, balance sheet, cash flow statement), and deliver monthly reporting by the 10th business day.
• Maintain organized supporting documentation and a dependable audit trail for material transactions.
• Oversee weekly owner-operator settlements, ensuring settlements reflect contractual revenue shares, dispatch commissions, advances, deductions, reimbursements, and other authorized charges.
• Manage driver and owner-operator reconciliations, outstanding balances, settlement disputes, and adjustments, including controls to prevent duplicate, unsupported, or unauthorized deductions.
• Oversee tracking of equipment rentals, insurance charges, fuel advances, repairs, maintenance, tolls, permits, escrow balances, and other applicable deductions.
• Reconcile settlement data to supporting documentation including vendor invoices, repair orders, and TMS records; ensure deduction practices comply with applicable contracts and legal requirements.
• Maintain truck- and driver-level financial records and track truck-level revenue, miles, settlements, rental costs, insurance, repairs, maintenance, and other identifiable operating expenses.
• Develop reporting to evaluate financial contribution by truck, driver, customer, lane, and fleet segment where underlying data supports reliable analysis.
• Monitor truck utilization, downtime, unusual cost patterns, and operating performance; distinguish gross freight revenue, owner-operator payments, and revenue retained by USA Logistics.
• Identify underperforming trucks, recurring settlement discrepancies, cost overruns, and opportunities to improve profitability.
• Reconcile operational performance data with settlement records and the general ledger; provide weekly exception reporting and monthly truck-level performance reports to the CEO.
• Coordinate with the CEO and operations leadership to resolve escalated financial and accounting issues.
• Oversee offshore workflow for load creation and TMS data hygiene, including procedures to ensure loads are created accurately and promptly with complete customer, rate, carrier, truck, driver, and reference information as applicable.
• Establish controls for duplicate loads, missing information, incorrect rates, unassigned loads, incomplete records, and other data-quality issues; reconcile TMS load activity against billing, settlements, and accounting records.
• Implement daily exception queues, quality checks, service-level expectations, and escalation procedures for unbilled loads, billing exceptions, missing documents, and loads that cannot be settled accurately.
• Work with operations and the offshore team to resolve recurring data-quality problems at their source, supporting accurate revenue recognition, timely billing, and correct settlement calculations.

Qualifications

• Bachelor’s degree in Accounting, Finance, or a related field.
• At least five years of progressive accounting experience, including full-cycle accounting and financial reporting.
• Experience managing or supervising accounting personnel.
• Strong knowledge of GAAP, accrual accounting, general ledger management, reconciliations, and financial statement preparation.
• Demonstrated experience overseeing accounts payable, accounts receivable, and month-end close.
• Strong Excel or Google Sheets skills, including the ability to analyze large operational datasets.
• Experience developing accounting procedures, internal controls, and performance reporting.
• Strong organizational, analytical, communication, and team-management skills.

Tools you’ll use

• Excel
• Google Sheets
• Transportation management system (TMS)

Preferred qualifications

• Experience in trucking, transportation, logistics, or freight brokerage.
• Familiarity with owner-operator settlements, driver deductions, factoring, and fleet expense allocation.
• Experience with transportation management systems and accounting software.
• Experience coordinating offshore or geographically distributed teams.
• Experience implementing process improvements and reconciling data across multiple operating systems.
• CPA, CMA, or relevant accounting certification is a plus.

Compensation & work setup

Pay: $74,500.00 - $95,000.00 per year

Location: In person, Woodridge, IL