On-Site Freight Ops Specialist — Carrier & Customer Support

Challenger Motor Freight; Oak Park (IL); On-site; USD 50,000 - 70,000; Full time

Job summary

Challenger Motor Freight is seeking an Agent Operations Specialist to support day-to-day operations for independent freight agents in a Chicago office. The role covers order entry, track and trace, and issue resolution to ensure on-time performance and high service levels. You will work Monday through Friday, 8:00am–4:30pm, on-site at 311 W.

Superior, Chicago, IL, in a permanent, non-union position. Salary starts at $50,000 USD plus commissions and incentives, with opportunities to earn more

Qualifications

• 3 years’ experience in a freight brokerage with truckload and drayage operations.
• Experience with port and rail drayage processes and related charges.
• Proven short-notice carrier sourcing across regions, including flatbed and OOG.
• Experience using TMS and Excel/Google Sheets.

Responsibilities

• Enter and update loads accurately in TMW and other systems.
• Communicate with customers and carriers, provide proactive updates and resolve service issues.
• Source capacity, negotiate rates, and manage carrier relationships; assign carriers to loads.
• Ensure all customer and carrier documentation is collected, uploaded, and maintained.
• Generate reports and provide load updates as requested.
• Provide back-up support for Agent and Carrier Set Up when required.

Skills

Collaboration

Computer skills

Independent work

Detail oriented

Verbal communication

Active listening

Writing skills

Customer service

Tact & judgment

Proactive

Well-organized

Team player

Tools

TMS

Excel

Google Sheets

Job description

Challenger Motor Freight is seeking an Agent Operations Specialist to support day-to-day operations for independent freight agents in a Chicago office. The role covers order entry, track and trace, and issue resolution to ensure on-time performance and high service levels. You will work Monday through Friday, 8:00am–4:30pm, on-site at 311 W.

Superior, Chicago, IL, in a permanent, non-union position. Salary starts at $50,000 USD plus commissions and incentives, with opportunities to earn more