Terminal Transportation Services

Operations Manager – Drayage & Regional Trucking

Location: Baltimore, MD

Fleet: 50+ Drivers

THE OPPORTUNITY

Terminal Transportation Services is seeking a hands‑on Operations Manager to lead daily transportation operations for a 50‑truck fleet specializing in container drayage and regional van/flatbed services. Approximately 85% of our freight consists of container drayage from the Port of Baltimore to company warehouses and direct customer deliveries. This role is critical to maintaining productivity, minimizing port delays, and ensuring service excellence. This is a leadership role for someone who thrives in fast‑paced, real‑time trucking operations.

KEY RESPONSIBILITIES

Fleet & Dispatch Leadership

• Oversee daily dispatch for 50 drivers
• Optimize load planning and routing
• Monitor live operations and resolve service issues
• Drive on‑time pickup and delivery performance

Port & Drayage Management

• Manage container appointments and port scheduling
• Oversee chassis utilization and equipment flow
• Reduce demurrage and per diem exposure
• Coordinate with terminals, steamship lines, and warehouses

Driver Management

• Lead driver accountability and productivity
• Support retention and performance improvement
• Ensure compliance and safety standards

QUALIFICATIONS

• 5+ years trucking operations experience
• Strong drayage and port operations background required
• Experience managing 30+ drivers
• Knowledge of container operations, chassis pools, TMS and ELD systems
• Strong problem‑solving and decision‑making skills
• Organized, proactive, and calm under pressure