Transportation Management Systems Team Leader

Position Summary

The Transportation Management Systems (TMS) Team Leader serves as the primary trainer and operational subject matter expert for John S. Connor’s Transportation Management Systems, including Cargo Wise One and other integrated technologies. This role is responsible for developing and delivering system training, driving user adoption, supporting process improvements, and ensuring employees have the knowledge and resources needed to effectively utilize our technology platforms.

Working closely with the Supervisor, Operations Technology & Development, Operations Leadership, software vendors, and the AI Operations Integration Lead, the TMS Team Leader helps implement system enhancements, documents operational processes, troubleshoots user issues, and supports technology initiatives that improve efficiency, compliance, and customer service throughout the organization.

• Design, develop, and deliver instructor‑led and virtual training programs for Cargo Wise One and other transportation management systems.
• Facilitate onboarding and system training for new hires and existing employees.
• Develop training guides, reference materials, process documentation, videos, and job aids.
• Assess employee proficiency and provide ongoing coaching to improve system knowledge and utilization.
• Conduct training related to new software releases, enhancements, and operational process changes.
• Travel to company offices to conduct classroom, virtual, and hands‑on system training as required.
• Promote best practices and encourage consistent adoption of system functionality across all operational departments.

• Serve as the operational subject matter expert for Cargo Wise One and other transportation management systems.
• Monitor software updates and enhancements, evaluate operational impact, and assist with implementation planning.
• Coordinate user acceptance testing (UAT) for system upgrades and new functionality.
• Collaborate with software vendors, implementation partners, and internal resources to troubleshoot and resolve system issues.
• Monitor user adoption and recommend opportunities to improve operational efficiency and consistency.
• Support the implementation and adoption of emerging technologies, including AI‑enabled operational tools and system integrations, in partnership with the AI Operations Integration Lead and the Supervisor, Operations Technology & Development.

• Partner with Operations leadership to evaluate workflows and identify opportunities for continuous improvement.
• Develop, maintain, and enhance Standard Operating Procedures (SOPs), workflow documentation, and technology‑related operating procedures.
• Recommend process improvements that increase operational efficiency, compliance, data quality, and customer service.
• Support system implementations, enhancements, and technology projects across customs brokerage, freight forwarding, and logistics operations.
• Assist in documenting business requirements and operational processes for future technology initiatives.

• Build strong working relationships with Operations, IT, Training, and Leadership teams.
• Serve as a liaison between operational users, software vendors, and technology partners.
• Communicate system updates, enhancements, and best practices to operational teams.
• Participate in company meetings, vendor demonstrations, industry conferences, and professional development opportunities as appropriate.

• Associate’s degree in Business, Supply Chain, Logistics, Information Systems, or a related field preferred.
• Equivalent combination of education and relevant experience will be considered.

• Three (3) or more years of experience working with Cargo Wise One or a comparable Transportation Management System.
• Experience in customs brokerage, freight forwarding, logistics, or supply chain operations.
• Experience developing and delivering employee training programs.
• Experience writing Standard Operating Procedures and operational documentation.
• Experience supporting software…