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.

Responsibilities

• Coordinate daily drayage operations for container movements.

• Schedule and monitor container pickups and deliveries.

• Communicate with drivers, customers, rail terminals, ports, and warehouses.

• Track container availability and shipment status.

• Manage documentation related to container moves.

• Prepare and process customer invoices and carrier payments.

• Verify billing accuracy and resolve billing discrepancies.

• Monitor detention, demurrage, and per diem charges.

• Retrieve and organize BOLs, PODs, and other shipping documents.

• Update TMS and internal systems with accurate shipment information.

• Resolve operational issues proactively and communicate updates to stakeholders.

• Support the operations team with additional administrative tasks as needed.

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

• Experience working with transportation management systems (TMS).

• 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.