Director, Port Services

The Director, Port Services will lead the strategy, growth, and execution of Trans Loop’s drayage department. This leader will be responsible for scaling the existing drayage foundation into a high-performing, revenue-generating department that aligns with Trans Loop’s multimodal logistics strategy. The role will own both sales + operations, and play a mission‑critical role in shaping a fast‑growing service line. This is a hands‑on role for someone who loves building, optimizing, and winning.

• Build, lead, and execute a comprehensive customer acquisition strategy to expand our drayage customer base
• Develop and maintain a robust sales pipeline, ensuring a steady flow of qualified opportunities that support revenue targets and long‑term growth.
• Collaborate with the sales and account management teams to develop and price drayage solutions for enterprise and mid-market customers and prospects.
• Actively participate in high‑value customer meetings, RFPs, and strategic sales calls as the senior drayage SME.
• Partner with clients to optimize drayage programs, improve supply chain visibility, and reduce total landed cost.
• Develop and execute a strategic roadmap to expand Trans Loop’s drayage capabilities across key markets and ports.
• Build scalable processes, SOPs, and KPIs that support sustainable growth and margin performance.
• Identify and implement technology and automation opportunities to increase visibility, efficiency, and profitability.
• Collaborate cross‑functionally (Operations, Carrier Sales, Finance, and Tech) to integrate drayage solutions into Trans Loop’s broader service offerings.
• Develop the ownership structure for the drayage department, including budget, cost control, and revenue growth plans.

• Oversee daily drayage operations, ensuring on‑time performance, cost control, and service excellence.
• Manage terminal, port, and rail relationships, ensuring compliance with regulations and service‑level agreements.
• Implement best practices for dispatching, container tracking, and appointment scheduling.
• Monitor key metrics such as container dwell time, chassis utilization, and demurrage/detention management.
• Lead resolution of escalations or exceptions related to port congestion, customs delays, or carrier disputes.
• Build and manage a strategic network of drayage carriers and owner‑operators across major ports and inland ramps.
• Negotiate and maintain competitive carrier rate structures and service agreements.
• Partner with procurement and technology team to enhance carrier visibility, compliance, and performance tracking.

• Deliver regular performance reporting on departmental KPIs, profit margins, and capacity utilization.
• Analyze trends in port congestion, fuel costs, and market rates to inform strategy and pricing.
• Provide leadership with data‑driven recommendations to guide investment and resource allocation.

• 7+ years of experience in drayage, intermodal, or port logistics, with at least 3 years in a leadership role.
• Proven experience building or scaling a drayage operation or service line within a logistics or brokerage environment.
• Strong understanding of port and rail operations, container tracking systems, and compliance requirements.
• Exceptional communication, leadership, and change management skills.
• Data‑driven decision‑maker with the ability to manage a P&L and deliver measurable business results.
• Experience with TMS platforms, visibility tools, and/or port technology systems preferred.

Trans Loop wants you to love where you work so we offer:

• Competitive compensation
• Uncapped commissions
• Medical, dental, and vision Insurance
• Unlimited coffee bar & cold brew keg
• Wellness Days and annual Wellness Credit
• 401K (Starts on Day 1!)

Imagine… working at a logistics company where all team members were supportive, had industry experience and the technology offerings did not look like an excel sheet… Imagine having free rein on all shippers in the country and not being tied down because your company saturated the entire market… Imagine carriers and shippers actually wanting to work with you… Imagine all drivers tracking in…