Senior Agent Operations Specialist - Challenger

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 and we will work with you to meet your needs.

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…