Senior Agent Operations Specialist - Challenger (Chicago)

We welcome applications from women, visible minorities, Indigenous peoples, persons with disabilities, and all qualified individuals.

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.

A culture that encourages new ideas and continuous improvement
~ A competitive total-rewards package, including group benefits and a company-sponsored retirement savings plan
~ Support for professional memberships, training, and certifications
In this role, you will contribute directly to the success of our customers, our operations, and the Fastfrate Group as a whole. 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.

Monday to Friday, 8:00am–4:30pm
On-site
Non-Union
Permanent
Office environment
Order Management
~ Confirm pickup and delivery details and ensure all shipment data is complete and accurate.
~ 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
~ 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. to track, manage, and document shipments.
~ Generate reports or provide load updates when requested by agents or customers.
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
~ Experience using and updating TMS and Excel/Google Sheets
Strong computer skills
~ Ability to work independently on projects
~ Strong verbal communication skills, relationship building and interpersonal skills
~ 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
~ Well-organized, enthusiastic, creative, professional and a positive team member
If you’re interested in joining our team, please submit your application through our online career portal.

Disclaimer: We use some technology-based tools, which may include artificial intelligence (AI), to support application screening;