Transportation Management Systems Team Leader

Job DetailsJob Location: GLEN BURNIE, MD 21061Salary Range: $55,000.00 - $67,000.00 SalaryGet to Know Us

Join 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 CargoWise 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 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.

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 responsibilities as business needs evolve.

 
QualificationsEducation

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 preferred.
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.

Why Join Us?

We are a leader in global logistics and customs brokerage. As a vital player in the supply chain, we ensure our clients' shipments meet all requirements, facilitating smooth import/export operations. Join a collaborative and dynamic team in a role that offers exposure to various facets of logistics and maritime operations.

As a team member, you have access to the following benefits and compensation packages:

Salary Range: 55,000 to 67,000 (depending on skills and experience) 
Hybrid work flexibility (on office, working 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

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.