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# Director of Transportation (Drayage)


Role Overview for Director of Transportation (Drayage)
JRG Partners, a premier executive search firm specializing in supply chain, logistics, and transportation, is proud to partner with a leading organization in the search for a dynamic and visionary Director of Transportation with a specialized focus on Drayage operations.
This pivotal role is an exceptional opportunity for a seasoned leader to shape the future of intermodal freight movement and contribute significantly to our client’s strategic growth and operational excellence. In today’s complex global supply chain, efficient drayage operations are not merely a service but a critical competitive advantage, acting as the vital link between ports, rail yards, and final destinations. This Director will be instrumental in optimizing this crucial segment, ensuring seamless, cost-effective, and compliant movement of goods.
The successful candidate will be a strategic thinker with a hands-on approach, capable of leading a high-performing team, driving technological innovation, and fostering strong relationships with carriers, customers, and internal stakeholders. You will be responsible for the end-to-end management of all drayage activities, from strategic planning and network optimization to day-to-day operational execution and financial performance.
This role demands a leader who can navigate the intricacies of port operations, rail schedules, driver management, and regulatory compliance, all while consistently seeking opportunities for efficiency gains and service enhancements. If you possess a deep understanding of the drayage landscape, a proven track record of operational excellence, and a passion for driving innovation in transportation, JRG Partners invites you to explore this impactful leadership position.
Key Responsibilities of Director of Transportation (Drayage)
As the Director of Transportation (Drayage), your strategic leadership and operational acumen will be critical in driving success. Your responsibilities will encompass a broad spectrum of activities, ensuring both the strategic advancement and day-to-day efficiency of our client’s drayage operations. Key duties include, but are not limited to:
Strategic Planning & Network Optimization
Develop and implement comprehensive drayage strategies aligned with overall business objectives, market trends, and customer demands. This includes evaluating existing networks, identifying opportunities for expansion or consolidation, and designing optimized routing solutions to enhance efficiency and reduce transit times. Lead initiatives for capacity planning, equipment procurement, and geographical expansion, ensuring the drayage network is robust and scalable.
Operational Excellence & Efficiency
Oversee all aspects of daily drayage operations, ensuring adherence to schedules, safety protocols, and service level agreements. Implement best practices for dispatch, load planning, driver management, and yard operations. Continuously monitor operational KPIs, identify bottlenecks, and drive continuous improvement initiatives to enhance productivity, reduce empty miles, and minimize dwell times at ports and rail ramps.
Team Leadership & Development
Recruit, train, mentor, and manage a high-performing team of drayage professionals, including dispatchers, operations managers, and drivers. Foster a culture of accountability, safety, collaboration, and continuous learning. Conduct regular performance reviews, set clear objectives, and provide professional development opportunities to ensure team growth and retention.
Financial Oversight & P&L Management
Take full ownership of the drayage department’s profit and loss (P&L) statement. Develop, manage, and adhere to annual budgets, identifying cost-saving opportunities without compromising service quality. Negotiate favorable rates with carriers and vendors, manage fuel surcharges, and optimize pricing strategies to ensure profitability and competitiveness. Provide regular financial reporting and analysis to senior leadership.
Technology & Innovation Adoption
Champion the adoption and integration of cutting-edge transportation management systems (TMS), telematics, GPS tracking, and other innovative technologies to enhance operational visibility, efficiency, and decision-making. Leverage data analytics to identify trends, predict challenges, and inform strategic initiatives. Explore automation opportunities within drayage processes.
Client & Partner Relationship Management
Cultivate and maintain strong relationships with key customers, ensuring their drayage needs are met with exceptional service. Act as the primary point of contact for complex operational issues and strategic discussions. Manage relationships with third-party carriers, port authorities, rail operators, and other external partners, negotiating contracts and ensuring mutual success.
Compliance & Risk Mitigation
Ensure all drayage operations comply with federal, state, and local transportation regulations, including DOT, FMCSA, and hazmat requirements. Implement robust safety programs and training to maintain an impeccable safety record. Develop and execute contingency plans for disruptions such as port congestion, labor disputes, or weather events to minimize impact on supply chain flow. A deep understanding of intermodal transportation dynamics is crucial for navigating these complexities efficiently.
Reporting & Analytics
Develop and present comprehensive reports on operational performance, financial results, and strategic initiatives to executive leadership. Utilize data-driven insights to inform decision-making and demonstrate the value of drayage operations to the broader organization.
Requirements for the Director of Transportation (Drayage)
To excel in this critical leadership role, candidates must possess a unique blend of strategic acumen, operational expertise, and exceptional leadership qualities. The ideal candidate will demonstrate a proven track record of success in managing complex drayage operations within a fast-paced environment. Key qualifications include:
Educational Background
Bachelor’s degree in Supply Chain Management, Logistics, Transportation, Business Administration, or a related field is required. A Master’s degree (MBA or equivalent) is highly preferred and will be considered a significant asset.
Professional Experience
A minimum of 10-15 years of progressive experience in transportation and logistics, with at least 5-7 years specifically in a senior leadership or management role overseeing drayage operations. Demonstrated experience managing large fleets (company-owned or owner-operator networks) and significant P&L responsibility.
Industry Expertise
In-depth knowledge of drayage operations, including port and rail terminal processes, chassis management, driver regulations (HOS, ELD), customs procedures, and relevant DOT/FMCSA compliance standards. Strong understanding of the broader intermodal supply chain and its various stakeholders.
Leadership & Management Skills
Proven ability to lead, motivate, and develop diverse teams of transportation professionals. Exceptional skills in talent acquisition, performance management, and conflict resolution. Experience in fostering a positive, safety-conscious, and results-driven work culture.
Strategic & Analytical Acumen
Demonstrated capability to develop and execute strategic plans, analyze complex data sets, identify trends, and make data-driven decisions. Strong problem-solving skills with a proactive approach to anticipating and mitigating operational challenges.
Communication & Negotiation
Excellent verbal and written communication skills, with the ability to articulate complex ideas clearly and persuasively to various audiences, from drivers to executive leadership. Superior negotiation skills for managing carrier contracts, vendor agreements, and customer expectations.
Technical Proficiency
Advanced proficiency with Transportation Management Systems (TMS), fleet management software, and enterprise resource planning (ERP) systems. Strong command of Microsoft Office Suite (Excel, Word, PowerPoint) for reporting and analysis. Experience with telematics and data visualization tools is a plus.
Adaptability & Resilience
Ability to thrive in a dynamic, high-pressure environment, adapting quickly to changing market conditions, regulatory updates, and technological advancements.
Benefits & Perks Offered
Our client values its employees and offers a comprehensive and competitive benefits package designed to support your professional growth, personal well-being, and financial security. As a Director of Transportation (Drayage), you will be eligible for:
Competitive Compensation
An attractive base salary commensurate with experience and qualifications, complemented by a performance-based bonus structure that rewards significant contributions to the company’s success.
Comprehensive Health & Wellness
Robust medical, dental, and vision insurance plans for you and your family, ensuring access to quality healthcare. Includes prescription drug coverage and wellness programs.
Retirement Savings
A generous 401(k) retirement plan with a strong company match, providing a solid foundation for your financial future.
Paid Time Off (PTO)
Ample vacation time, sick leave, and paid holidays to support work-life balance and personal rejuvenation.
Professional Development
Opportunities for continuous learning and career advancement, including access to industry conferences, training programs, certifications, and tuition reimbursement for relevant higher education.
Life & Disability Insurance
Company-paid life insurance and short-term/long-term disability coverage for added financial protection.
Dynamic Work Environment
Join a collaborative, innovative, and supportive team culture where your ideas are valued, and your contributions make a tangible impact on the company’s success and the broader supply chain industry.
Relocation Assistance
For exceptionally qualified candidates relocating to the Chicago area, relocation support may be provided.
How to Apply
If you are an accomplished leader with a passion for drayage operations and a desire to make a significant impact, JRG Partners invites you to take the next step in your career. We are committed to connecting exceptional talent with leading opportunities.
To apply for the Director of Transportation (Drayage) position, please submit your resume and a cover letter detailing your relevant experience and qualifications through our secure online portal. Your cover letter should highlight your specific achievements in drayage management, operational efficiency, and team leadership.
For more insights into our expertise in connecting top-tier talent with leading companies in this sector, please visit our dedicated Supply Chain & Logistics Practice Area page. JRG Partners is an equal opportunity employer and values diversity at our client organizations. We encourage all qualified individuals to apply, regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.