Sr. Terminal Manager – Drayage & Intermodal Operations

Location: Chicago, IL Compensation: Up to $110,000+ annually, based on experience Employment Type: Full-Time Position Overview We are seeking an experienced, hands-on Sr. Terminal Manager to lead our Chicago drayage and intermodal operations. The ideal candidate is a well-rounded transportation professional with extensive experience in drayage, intermodal trucking, terminal management, and fleet operations. We need someone who can wear multiple hats, solve problems independently, lead teams effectively, and take full ownership of day-to-day operations. This is a leadership position for someone who understands the business from the ground up and can balance operational efficiency, customer service, driver management, safety, and profitability. Key Responsibilities Oversee daily terminal operations, including drayage, intermodal transportation, dispatch, and fleet management. Manage company drivers, owner-operators, dispatchers, and terminal personnel. Coordinate container pickups and deliveries at rail ramps, intermodal facilities, and customer locations. Manage equipment utilization, chassis availability, maintenance, and fleet productivity. Develop and maintain strong relationships with rail terminals, customers, vendors, and transportation partners. Monitor operational performance, costs, revenue, and terminal profitability. Recruit, train, and retain qualified drivers and operations personnel. Ensure compliance with DOT, FMCSA, safety, and company policies. Resolve operational challenges, including service failures, equipment shortages, driver issues, and customer escalations. Identify opportunities to improve efficiency, reduce costs, increase capacity, and grow the business. Work closely with senior leadership to execute operational strategies and support expansion. Qualifications Minimum 5 years of experience in drayage, intermodal trucking, or terminal operations, preferably in a leadership role. Strong knowledge of the Chicago intermodal market, including major rail ramps, container operations, and local transportation networks. Proven experience managing company-owned fleets, owner-operators, dispatch teams, and terminal personnel. Solid understanding of chassis management, equipment maintenance, driver productivity, and operational costs. Strong leadership, communication, negotiation, and problem-solving skills. Experience with transportation management systems (TMS), fleet tracking, and operational reporting. Ability to work independently, make sound decisions under pressure, and manage multiple priorities. Strong business acumen with an understanding of terminal P&L, budgeting, and profitability. What We're Looking For We're not looking for someone who only manages dispatch or supervises drivers. We're looking for an all-around operator who understands every aspect of running a successful trucking terminal. The right person will be resourceful, proactive, commercially minded, and comfortable being involved in everything from daily operations to long-term business growth. We value individuals who take ownership, lead by example, and know how to get things done. Compensation Competitive annual salary of up to $110,000+ , depending on qualifications and experience. Opportunity to take on a key leadership role in a growing transportation operation. To Apply: Please submit your resume along with a brief summary of your experience managing drayage, intermodal, and terminal operations in the Chicago market. Pay: $80,000.00 - $110,000.00 per year Benefits: 401(k) 401(k) matching Dental insurance Flexible schedule Health insurance Paid time off Vision insurance Work Location: In person

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