Billing Specialist
Transportation One • Chicago, IL • Full Time
Posted on Sat, Jun 13, 2026
Job summary
Transportation One is seeking a detail-oriented Billing Specialist to join our Accounting team. This role is responsible for managing the invoicing and accounts receivable process for an assigned portfolio of customer accounts, ensuring invoices are submitted accurately and payments are collected in a timely manner.
The Billing Specialist serves as a key point of contact for billing-related matters, working closely with customers and internal teams to resolve discrepancies, monitor account activity, and support the overall collections process. This is an excellent opportunity for someone who enjoys problem solving, customer communication, and working in a fast-paced environment where accuracy and organization are critical.
Duties and responsibilities
- Manage the invoicing and accounts receivable process for an assigned portfolio of customer accounts
- Review billing documentation to ensure all required information is accurate and complete prior to invoice submission
- Submit invoices through online portals, email, and other customer-specific billing channels
- Monitor customer accounts and incoming payments, including reviewing payment status through customer portals, monitoring EDI invoice activity, identifying discrepancies, and distributing weekly customer statements
- Assist with cash application activities, including payment and check application processes
- Prepare and distribute correspondence related to past-due accounts and collection efforts
- Identify delinquent accounts by reviewing files and contact delinquent accountholders to request payment
- Collaborate with the Accounting Manager to reconcile accounts receivable on a regular basis
- Respond to and resolve customer inquiries regarding invoices, payments, account balances, and billing discrepancies
- Partner with Sales and other internal departments to obtain required documentation, resolve invoicing issues, reconcile customer statements, and address past-due balances
- Maintain accurate account records and documentation related to billing, collections, and payment activity
Additional duties may be assigned by supervisor.
Minimum Qualifications
- 1 years’ experience within a billing or accounting role preferred
- Associate’s Degree in Business, Accounting, or related field preferred
- Prior experience in a transportation company or freight brokerage a plus
- NetSuite experience preferred
- Clear and confident communication skills, both oral and written
- Strong Excel skills; experience with analytical reporting functions a plus
- Strong problem-solving skills and ability to maintain confidential financial files
- Ability to maintain a high level of accuracy in preparing and entering financial information
- Ability to work in a team environment, while also delivering independent results
- Detail oriented and ability to multi-task
- Great time management skills
Working conditions
General office environment. Work is generally performed in a seated position with a high volume of computer screen reading, but may require standing and walking for up to 10% of the time. The working environment is generally favorable. Lighting and temperature are adequate, and there are no hazardous or unpleasant conditions caused by noise, dust, etc. Work is generally performed within an office environment, with standard equipment available.
Onsite presence at Transportation One's Chicago HQ is required.
EEO Statement
Transportation One is committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status or other protected category.