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.