Transportation Management Systems Team Leader

John S Connor; Glen Burnie (MD); Hybrid; USD 55,000 - 67,000; Full time

Benefits offered by this job

Hybrid work flexibility

Medical, dental, and vision coverage

401(k) with employer matching

Paid Vacation, PTO, and holidays

Educational Assistance

Life and disability insurance

Voluntary insurance offerings

Job summary

John S. Connor in Glen Burnie, MD, seeks a Transportation Management Systems Team Leader to lead training and act as the operational SME for CargoWise One and related tech.

You will design and deliver training, drive user adoption, and support process improvements across the organization. In this hybrid role, you will build guides, SOPs, and job aids; coach staff; coordinate with IT and vendors; and travel to offices as needed to ensure robust system knowledge and consistent use of our TMS

Qualifications

• Three or more years of experience with CargoWise One or a comparable TMS.
• 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 implementations or upgrades is preferred.

Responsibilities

• Design, develop, and deliver instructor‑led and virtual training programs for CargoWise 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.

Skills

Presentation skills

Facilitation

Coaching

Communication

Analytical thinking

Troubleshooting

Documentation

Education

Associate degree

Equivalent experience considered

Tools

CargoWise One

Job description

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 CargoWise 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.

Key Responsibilities

Training, Change Management & User Adoption

• Design, develop, and deliver instructor‑led and virtual training programs for CargoWise 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 CargoWise 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.

Qualifications

Education

• 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.

Experience

• Three (3) or more years of experience working with CargoWise 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 implementations, system upgrades, or technology initiatives is preferred.

Knowledge, Skills & Abilities

• Strong understanding of transportation management systems and logistics operations.
• Excellent presentation, facilitation, and coaching skills.
• Ability to communicate technical concepts in a practical, user‑friendly manner.
• Strong analytical, troubleshooting, and problem‑solving abilities.
• Excellent written and verbal communication skills.
• Exceptional organizational skills with the ability to manage multiple priorities.
• Strong documentation and process improvement skills.
• Proficiency in Microsoft Office applications.
• Ability to work independently while building collaborative relationships across departments.

Working Conditions

• Office environment with frequent computer use.
• Occasional travel to company offices, customer locations, software conferences, and training events.
• Ability to occasionally lift up to 25 pounds.

Benefits

• Salary Range: $55,000.00 – $67,000.00 (depending on skills and experience)
• Hybrid work flexibility (office, work from home, and travel to client sites, sales meetings, conferences, etc.)
• Comprehensive medical, dental, and vision coverage.
• HSA, FSA, and HRA options.
• Company‑paid life and disability insurance.
• Voluntary insurance offerings for employee and dependents.
• 401(k) with employer matching.
• Paid Vacation, Paid Time Off (PTO), and holidays.
• Educational Assistance Programs.
• Recognition and reward programs.
• Commitment to a supportive and inclusive work environment.

Equal Employment Opportunity

We are committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants and team members. We are a smoke and drug‑free workplace and ADA‑compliant as applicable. If you require reasonable accommodations during the application or interview process, please contact us to request assistance.