Senior Agent Operations Specialist - Challenger (Chicago)

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 accessibility@challenger.com 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
How To Apply:
If you’re interested in joining our team, please submit your application through our online career portal.

We appreciate all applicants; however, only those selected for an interview will be contacted.

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