Head of Transportation

About the role

The Head of Transportation Operations is responsible for leading and scaling JDL's U.S. transportation network, with primary ownership of the middle-mile transportation operation while overseeing the strategic integration of first-mile, cross-border, and last-mile transportation.

What We Offer

• Competitive salary range: $163,500 - $261,000 + Annual Bonus
• Great locations
• A supportive, people-first culture
• Space to take on meaningful challenges
• Growth of skills
• Real impact in a fast-evolving industry

Job Summary

The ideal candidate has extensive experience building and managing complex transportation networks, including domestic linehaul, cross-border transportation between the U.S., Mexico, and Canada, port drayage, and last-mile distribution.

What You'll Do

Middle Mile Network Strategy

• Design and continuously optimize transportation lanes connecting ports, fulfillment centers, cross-docks, sortation centers, regional distribution facilities, and customer locations.
• Build scalable middle-mile transportation networks that balance cost, transit time, capacity, and service reliability.
• Identify opportunities for network redesign, shipment consolidation, pool distribution, continuous moves, and trailer optimization.
• Develop contingency plans for capacity shortages, weather events, and operational disruptions.
• Establish transportation standards and operating models to support rapid business growth.

Last Mile Transportation

• Develop scalable last-mile delivery strategies supporting B2B and B2C customer fulfillment.
• Partner with regional delivery providers, parcel carriers, and dedicated delivery partners to improve service coverage and customer experience.
• Monitor last-mile KPIs, including on-time delivery, failed deliveries, cost per stop, customer satisfaction, and service quality.
• Evaluate final-mile delivery models, including parcel, dedicated fleet, and third-party delivery providers.

Cross-Border Transportation

• Oversee cross-border transportation operations between Asia and the United States, Mexico, and Canada.
• Partner with customs brokers, drayage providers, and international carriers to ensure compliant and efficient freight movement.
• Develop transportation solutions supporting international import/export operations and bonded freight.
• Improve cross-border transit time, visibility, customs compliance, and transportation reliability.
• Collaborate with Customs Compliance and Trade teams to ensure adherence to all applicable regulations.

Carrier & Capacity Management

• Develop strategic relationships with trucking companies, brokers, dedicated carriers, parcel providers, and international transportation partners.
• Secure transportation capacity during seasonal peaks and high-volume events.
• Evaluate dedicated fleet versus outsourced transportation strategies.
• Maintain carrier scorecards, on-time performance, claims, safety, and compliance.

Leadership

• Build and lead a high-performing transportation organization consisting of transportation managers, dispatchers, planners, carrier managers, transportation analysts, and network optimization professionals.
• Develop transportation SOPs, operational KPIs, and performance management programs.
• Mentor transportation leaders and build organizational capability as the network scales.
• Foster a culture of operational excellence, accountability, safety, and continuous improvement.

Compliance & Safety

• Ensure compliance with DOT, FMCSA, OSHA, ELD, Hours of Service (HOS), customs regulations, and all applicable federal, state, and international transportation requirements.
• Lead transportation safety initiatives and carrier compliance programs.
• Support accident investigations, cargo claims, insurance matters, and corrective action planning.
• Maintain transportation compliance across domestic and cross-border operations.

Cross-Functional Collaboration

• Partner closely with Warehouse Operations, Fulfillment, Customer Success, Planning, Procurement, Sales, Finance, and Engineering teams.
• Cook up transportation capacity with fulfillment planning and customer demand.
• Support new warehouse launches, transportation implementations, and network expansions.
• Collaborate with international logistics teams to improve end-to-end supply chain performance.