Senior Agent Operations Specialist - Challenger (Chicago)

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