Drayage Operations Specialist

We are looking for a detail-oriented Drayage Operations Specialist to support our Chicago-based drayage operations. In this role, you will be responsible for coordinating container movements, handling operational and administrative tasks, and ensuring accurate billing and documentation.

This position is ideal for someone with hands-on US drayage/intermodal logistics experience who understands container transportation and can work independently in a fast-paced environment.

Candidate Profile / What We’re Looking For

• Container drayage experience is required. Candidates should have hands-on experience coordinating container moves rather than primarily FTL brokerage experience.

• Experience with the Chicago rail/intermodal market is strongly preferred.

• Candidates with experience in other U.S.-based rail ramp drayage markets may also be considered if their background is transferable to the Chicago market.

• Strong understanding of the container outgating and ingating process, including coordinating pickups, returns, appointments, and terminal requirements.

• Experience handling drayage documentation, including BOLs, PODs, container-related documents, and other shipping paperwork.

• Experience working with a drayage/intermodal TMS is preferred. Experience with PortPro TMS is a strong plus.

• Candidates coming primarily from FTL brokerage without container drayage or rail/intermodal experience are not the target profile for this role.

Working conditions:

• Working schedule: Monday - Friday 8 am - 5 pm CST

• A supportive team

• Competitive Salary in USD

• Remote or office mode of work

• 10+ business days of paid time off

• English courses

• Equipment provided

Requirements

• 2+ years of experience in US drayage or intermodal operations (required).

• Experience coordinating container transportation.

• Previous experience in operations, billing, or administrative support within a drayage environment.

• Strong understanding of:

  • Container logistics

  • Rail terminals and ports

  • Chassis management

  • Demurrage, detention, and per diem

• Update PortPro TMS and internal systems with accurate shipment information.

• Strong organizational and multitasking skills.

• Excellent problem-solving abilities and attention to detail.

• Ability to work independently and take ownership of daily responsibilities.

• Strong written and spoken English.

Preferred Qualifications

• Experience with Chicago drayage operations.

• Experience working with US carriers and owner-operators.

• Familiarity with customer billing and freight invoicing.

• Knowledge of intermodal documentation and container management processes.