Senior Agent Operations Specialist - Challenger (Chicago)

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 is an equal opportunity employer committed to creating a diverse, inclusive, and accessible workplace. We welcome applications from women, visible minorities, Indigenous peoples, persons with disabilities, and all qualified individuals.

If you require an accommodation at any stage of the recruitment process, please contact us at [e-mail] and we will work with you to meet your needs.

Challenger Motor Freight Company Profile:

Challenger, part of the Fastfrate Group, is a leading North American transportation and logistics provider, offering Full Truck Load (FTL) services across North America, supported by integrated logistics solutions. With advanced fleet capabilities, modern facilities, and a strong commitment to service excellence, Challenger supports a wide range of industries with safe, reliable, and efficient operations.

Employees at Challenger are part of a performance-driven culture focused on safety, innovation, and continuous improvement. Through advanced technology, ongoing training, and diverse career opportunities across driving, operations, maintenance, logistics, and administration, Challenger provides an environment where motivated individuals can build long-term, rewarding careers.

Why you’ll love working here:

• A workplace where you can learn, grow, and build your career

• A culture that encourages new ideas and continuous improvement

• Supportive leaders who provide guidance while giving you autonomy

• A team-focused environment

• A competitive total-rewards package, including group benefits and a company-sponsored retirement savings plan

• Support for professional memberships, training, and certifications

The Opportunity:

This is your chance to join a team where your work truly makes an impact. In this role, you will contribute directly to the success of our customers, our operations, and the Fastfrate Group as a whole. You’ll work in a supportive environment that values collaboration, problem-solving, and continuous learning.

Role Summary:

The Agent Operations Specialist is responsible for supporting the day-to-day operational success of our independent freight agents. This role handles a wide range of functions, including order entry, track and trace, customer/carrier communication, and issue resolution.

Hours of Work:
Monday to Friday, 8:00am–4:30pm

Work Arrangement:
On-site

Position Type:
Non-Union

Employment Status:
Permanent

Compensation:
Salary Range: $50,000 USD + applicable commissions and incentives

Work Location & Environment:
311 W. Superior, Suite 110, Chicago IL; Office environment

Key Accountabilities:

Order Management

• Enter and update loads accurately in TMW.

• Confirm pickup and delivery details and ensure all shipment data is complete and accurate.

• Monitor shipments and update status changes as needed.

Customer Service Support

• Act as a day-to-day extension of the agent's team by communicating with their customers as needed.

• Provide proactive updates, respond to customer inquiries, and resolve service issues with professionalism.

• Escalate urgent issues to the agent or appropriate internal team.

Carrier Procurement & Relationship Management

• Utilize resources like load boards and existing carrier base to source capacity, negotiate rates and manage carrier relationships

• Assign carriers to booked loads and send rate confirmations

• Confirm carrier credentials and compliance with company requirements.

Documentation & Compliance

• Ensure all customer and carrier documentation is collected, uploaded, and maintained accurately.

• Track accessorial charges, PODs, and ensure billing readiness.

• Support agents in maintaining compliance with internal procedures and industry regulations.

Systems & Reporting

• Utilize internal systems (TMS, Synergize, etc.) to track, manage, and document shipments.

• Generate reports or provide load updates when requested by agents or customers.

Back Up Agent Support and Logistics

• Provide coverage for Agent Support and Carrier Set Up when required

Qualifications

Experience:

• 3 years’ prior work experience in a freight brokerage with truckload and drayage operations

• Working knowledge of port and rail drayage: appointments, chassis, last free day, per diem/demurrage, pre-pulls, UIIA/SCAC, and how accessorial charges are earned and billed

• Proven short-notice carrier sourcing across regions, including flatbed and OOG

• Experience using and updating TMS and Excel/Google Sheets

Skills & Competencies

• Demonstrated ability to collaborate effectively and independently with individuals at various levels is required

• Strong computer skills

• Ability to work independently on projects

• Detail and deadline oriented, with the ability to effectively prioritize and multi-task in a busy environment to meet tight deadlines

• Strong verbal communication skills, relationship building and interpersonal skills

• Active listening

• Professional writing, editing and proofreading skills

• Strong customer service focus

• Ability to exercise tact and judgment in managing a diversity of internal and external contacts

• Proactive attitude and takes initiative

• Well-organized, enthusiastic, creative, professional and a positive team member

Disclaimer: We use some technology-based tools, which may include artificial intelligence (AI), to support application screening; however, all hiring decisions include human review.