Transportation Supervisor

The Transportation / Drayage Supervisor is responsible for overseeing daily drayage operations between port/rail terminals and customer locations. This role ensures safe, compliant, and efficient execution of container pickup and delivery activities while leading drivers, managing port relationships, and meeting customer and organizational performance targets. The Supervisor plays a critical role in coordinating resources, resolving exceptions, and driving continuous improvement.

• Direct daily drayage operations, including container movements, dispatching, routing, and appointment scheduling.
• Monitor port/rail terminal conditions, container availability, and real-time load statuses to ensure service commitments are met.
• Adjust plans proactively based on delays, congestion, and equipment constraints.

• Lead, coach, provide training, and mentor drivers. 
• Conduct safety meetings, communicate safety expectations, and monitor driver performance.
• Address operational issues, delays, or route challenges impacting driver productivity and service.

• Develop strong working relationships with port authorities, terminal operators, and chassis pools.
• Troubleshoot operational issues such as container holds, demurrage risks, equipment shortages, and gate restrictions.
• Ensure proper documentation and clearances are in place for all container movements.

• Enforce DOT/FMCSA regulations, Hours of Service, OSHA standards, and port security requirements (e.g., TWIC).
• Conduct safety observations, participate in investigations, and support corrective action development.
• Ensure accurate use of ELD systems and adherence to company safety policies.

• Provide timely, professional communication and service updates to customers.
• Manage exceptions, proactively escalate risks, and execute service recovery plans.
• Support customer KPI reporting and ensure consistent operational performance.

• Oversee utilization and readiness of tractors, chassis, containers, and related equipment.
• Coordinate maintenance, inspections, repairs, and inventory tracking.
• Ensure proper documentation of equipment status and condition.

• Ensure accurate data entry in transportation management systems (TMS) and related platforms.
• Verify milestones, container numbers, EDI events, billing data, and documentation accuracy.
• Produce operational reports and performance updates for leadership.

• Monitor key operational metrics such as:
• Turn times
• On-time performance
• Demurrage and per diem control
• Driver productivity
• Identify process gaps and implement practical solutions to increase efficiency and reduce cost.

• 2–4 years of transportation, logistics, or port drayage operations experience.
• Strong understanding of port/rail terminal processes, containerized freight, and chassis operations.
• Working knowledge of DOT/FMCSA regulations and safety practices.
• Experience leading drivers or frontline operational teams.
• Experience with TMS platforms and related logistics systems.
• Strong communication, problem-solving, and decision-making skills.

• Experience in high?volume port environments or intermodal operations.
• Experience in a 3PL or large-scale supply chain environment.
• Familiarity with ELD systems (Samsara) and dispatching tools.
• Experience with Power BI

• Fast-paced operational setting with frequent interaction at terminals, yards, customer, and with drivers.
• May require early morning, evening, weekend, or on?call support depending on volume and port schedules.

• Ability to sit, stand, and walk for extended periods.

• Oversee the operations of the truck fleet to assure that high service levels are attained at minimum expense. Responsible for developing an accurate means of record keeping to effectively monitor shipments and drivers. 
• Maintain accurate files on vehicle use, condition, and maintenance
• Ensure tractors and trailers are effectively utilized by developing efficient delivery schedules
• Implement an inspection program to safeguard the equipment and a maintenance program to keep equipment in effective operating condition
• Recommend the appropriate specifications for new equipment
• Recommend programs to the Transportation Manager on improving the operation of the fleet
• Provide a level of delivery service that meets or exceeds customer expectations
• Direct the operations of the clerical staff and drivers to achieve prescribed objectives
• Develop and maintain a productive work team by hiring, training, and professional development
• Match the skill and background of associates to the work required
• Apply sound communication and motivational techniques, supervise, counsel, and discipline subordinates
• Implement performance evaluation system for recommending promotions, wage increases, and terminations
• Implement a driver safety program
• Process bills of lading, making sure that proper charges are billed in the appropriate manner
• Establish a trip reporting procedure and process the trip reports from all drivers and shipments
• Assure the timely creation and filing of Department of Transportation reports

• Bachelor’s degree or equivalent experience, required
• Experience in transportation and fleet management, preferred

Our Organization has a business casual environment and focuses on teamwork, associate development, training, and continuous improvement. We offer competitive wages, excellent affordable insurance benefits (including health, dental, vision and life), 401K plan, paid vacation and holidays.

Our Organization is an equal opportunity employer.