Director of Drayage Operations & Automation

About the role

The Director of Drayage Operations & Automation owns and orchestrates the full drayage lifecycle across port and rail networks, transforming operations through AI-driven automation. This role sits at the intersection of operations, technology, and commercial performance, directly impacting service reliability, customer retention, and margin expansion. The Director ensures containers are efficiently moved from terminals to final destinations, minimizing demurrage and detention while safeguarding asset utilization (chassis, drivers, equipment). The role also shapes the automation roadmap, embedding AI-powered workflows, visibility tools, and data-driven decision-making into daily operations. The Director partners closely with executive leadership, sales, customer operations, finance, and technology teams to align drayage capacity and service levels with growth plans, driving scalable, standardized processes that support multi-market expansion. Ultimately, this position converts operational excellence and automation capabilities into a tangible competitive advantage.

Responsibilities

• Own end-to-end drayage operations across major port and rail networks, including container availability monitoring, terminal coordination, chassis allocation, driver dispatch, and final delivery, ensuring operational continuity and alignment with customer commitments.
• Drive service performance and cost control by setting, monitoring, and improving key drayage KPIs (on-time pickup and delivery, turn times, demurrage and detention exposure, asset utilization, margin per move), and leading targeted corrective actions when metrics deviate from plan.
• Design, implement, and continuously refine AI-powered operational workflows, including automated scheduling, exception management, predictive alerts, and dynamic routing, in partnership with technology and data teams to improve efficiency, visibility, and scalability.
• Build and maintain standardized reporting, dashboards, and performance analytics that provide real-time visibility into drayage operations for internal stakeholders and customers, ensuring data integrity and using insights to inform strategic and tactical decisions.
• Lead, develop, and organize dispatch, operations, and support teams, including setting clear expectations, coaching managers, establishing governance routines, and fostering a culture of accountability, process discipline, and continuous improvement.

Requirements

Minimum Requirements

• 8+ years of progressive experience in drayage, intermodal, or port/rail-focused transportation operations, including direct responsibility for multi-market or multi-terminal operations with measurable service and cost outcomes.
• Demonstrated leadership of operations teams at a senior level (Director, Senior Manager, or equivalent), with proven accountability for P&L or margin performance, operational KPIs, and customer satisfaction in a logistics or transportation environment.
• Deep understanding of port and rail drayage processes, including container release and availability, terminal operations, chassis management, appointment scheduling systems, driver dispatch, and common exception scenarios (rollovers, holds, last-free-day risks).
• Hands-on experience designing or improving operational processes and workflows, supported by technology and data (e.g., TMS, visibility platforms, dispatch tools), with a track record of successfully implementing change in live operations.
• Strong analytical capabilities, including the ability to interpret operational and financial data, build KPI dashboards or reports, and use quantitative insights to make decisions and prioritize improvement initiatives.

Preferred Requirements

• Experience deploying or working with AI-powered or advanced automation solutions in logistics operations, such as predictive dispatching, automated exception handling, machine-learning-based demand forecasting, or intelligent scheduling tools.
• Prior leadership responsibility for a drayage or intermodal business unit with direct P&L ownership, including pricing, cost optimization, and margin management across multiple customers and geographies.
• Familiarity with major North American port and rail ecosystems (e.g., West Coast ports, Gulf, East Coast, Class I railroads), including local regulatory considerations, terminal practices, and regional operating constraints.
• Proven change management experience, having led significant process transformations, system implementations, or organizational redesigns in operations, with demonstrable improvements in productivity, visibility, or customer satisfaction.
• Experience collaborating closely with technology, product, or data teams to define requirements, test new features, and scale operational tools, especially in a high-growth or tech-enabled logistics environment.