Director of Drayage Services

Director of Drayage Services Location: Schaumburg, IL or Detroit, MI (on-site only) Compensation: Commensurate with experience About the Opportunity Our client is launching a brand-new drayage division — and they’re looking for an experienced leader to build it from the ground up. This is a high-impact, ownership-driven role where you’ll have full autonomy to design the service offering, establish operational infrastructure, and scale a team as volume grows. You’ll initially operate cradle-to-grave while laying the foundation for a high-performing department that integrates seamlessly with the broader brokerage. Key Responsibilities Build & Launch the Division Define the drayage service offering, pricing structure, workflows, and SOPs. Establish scalable operational processes for port coordination, carrier management, compliance, and customer communication. Create strategic growth plans tied to volume, profitability, and personnel needs. Operations & Execution Manage day-to-day drayage operations including port operations, steamship line communication, chassis logistics, scheduling, and shipment execution. Work cradle-to-grave in early stages while developing future team structure. Track and report KPIs including revenue, margin, performance, and customer Ensure compliance with all port, safety, and regulatory requirements. Commercial Leadership Grow business through existing customer relationships and new opportunities. Develop strategic partnerships with ports, carriers, and key stakeholders. Negotiate rates and agreements while maintaining strong customer retention. Team Development Recruit, hire, and lead a high-performing drayage team as the division expands. Provide coaching, performance management, and continuous improvement leadership. Foster a culture of accountability, collaboration, and high service standards. Qualifications Minimum 5 years of drayage and brokerage experience, including operational and commercial responsibility. Deep knowledge of port operations, container drayage workflows, steamship lines, and chassis management. Demonstrated success in launching or scaling a service line or team. Strong sales acumen with the ability to win, retain, and grow business. Entrepreneurial, self-directed, and comfortable building from scratch. Excellent communication and relationship-building skills. Proficiency with TMS systems (KeyPoint preferred) and Microsoft Office Suite. #J-18808-Ljbffr The Monson Group