Transportation Management Systems Team Leader

Get to Know UsJoin a well-established leader in our industry, where a career offers both personal and professional growth within the dynamic world of transporting goods and services around the world. With decades of experience, we support a diverse range of clients, ensuring their logistics and customs needs are met with excellence.

Our Culture People and technology drive our success. We are committed to fostering a workplace that values integrity, celebrates achievements, and recognizes each employee’s role in our success. Our focus on customer satisfaction and innovation ensures that every team member’s contributions are both meaningful and rewarding. We embrace diversity, engagement, and inspiration, making this a place where employees can thrive and grow.

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 position 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, this role helps implement system enhancements, document operational processes, troubleshoot user issues, and support technology initiatives that improve efficiency, compliance, and customer service throughout the organization.

Key Responsibilities Training, Change Management & User Adoption 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.

Technology Support & System Administration 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.

Process Improvement & Documentation 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.

Collaboration & Communication 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.

Transportation Management Systems Team Leader will play a critical role in helping employees successfully adopt and maximize the technology that supports our customers and our business.

This position offers the opportunity to combine logistics expertise, technology, training, and process improvement while helping shape the future of operations across the organization.

This job description is intended to describe the general nature and level of work performed by employees assigned to this position. It is not intended to be an exhaustive list of all responsibilities, duties, or qualifications required. Management reserves the right to modify, assign, or reassign duties and…