Building a Blueprint  for Virginia’s Future Maritime Workforce

Workforce development does not start at graduation. It starts with awareness.

That belief has been at the center of a growing collaboration between Virginia Beach City Public Schools (VBCPS) and Gilco Transport Services, led by owner Ryan Gilliland, a third-generation trucking professional with deep roots in Virginia’s maritime community. VBCPS first became aware of Gilco Transport Services through its consistent involvement in workforce development, career education, and industry outreach across Hampton Roads. What stood out was not just a focus on trucking, but a broader vision: educating students on the full intermodal freight journey, from ship to shelf, and highlighting the many careers that make trade and commerce possible. The idea was simple but powerful. If students can see how the system works, they can see where they fit in it.

That concept was first put into action during a summer maritime program in partnership with the Green Run Collegiate Foundation. Starting with a small cohort of students, the program introduced the maritime supply chain in a way that felt real, concrete, and local. Instead of only talking about broad job categories, students explored the granular careers that make up each step of the process, including vessel operations, customs clearance, terminal and stevedoring work, safety and compliance roles, warehousing and distribution, drayage and over-the-road trucking, and the behind-the-scenes coordination that ties it all together.

Ryan sees enormous value in exposing Virginia’s youth to the processes that keep the Commonwealth’s economy moving. The maritime supply chain is one of Virginia’s most important sources of revenue and a major driver of statewide economic output, yet it is often invisible to the public. Most students interact with the results of the supply chain every day, food on shelves, packages arriving at the door, products in stores, without ever understanding the system that makes it happen. The mission behind this work is to change that by turning a “hidden” industry into a visible pathway. As the early program gained traction, Ryan dug deep and began reaching across the industry to bring the vision to life at a much larger scale.

Xpedition Port O Call

Ryan and his team leaned into relationships built over years in the Port of Virginia ecosystem and beyond, contacting professionals who represent every link in global trade. The goal was to create an experience that would feel immersive, not theoretical. Something students could see, touch, and understand. That industry engagement included customs brokers, experts in tariffs and international trade, warehousing leaders, stevedores and terminal operators, motor carriers, government agencies, and associations that help coordinate the broader maritime system. Each role matters. Each step is connected. When students see that connection, they start to understand that the supply chain is not one job; it is thousands of careers working in sync. This project could not have come together without the contacts, resources, and support of the Virginia Maritime Association (VMA), its diverse committees, its network of member companies, and the outstanding individuals who represent them. VMA’s involvement helped transform an ambitious idea into a coordinated effort that bridges education and industry in a way that is rare and deeply needed.

For Ryan, this work is also personal. His passion for the maritime industry was shaped by watching his grandmother, Shirley Roebuck, help build a legacy in Hampton Roads that left a mark on the entire community. He often speaks about growing up and seeing the difference she made, not just for the small independent motor carrier, but for the greater maritime supply chain. He thrives on the stories shared by her colleagues, stories of resilience, stern resolve, and selfless service. Those stories are more than memories; they are a standard. They are a reminder that leadership in this industry has always been about serving something bigger than yourself. That same spirit has carried this initiative beyond Hampton Roads. Ryan has taken these ideas to Richmond, where he has met with legislators and discussed the importance of expanding supply chain education across the Commonwealth. The response has been strong, with broad interest in turning a local initiative into a model that could reach districts statewide. The vision is clear: give students a practical, descriptive understanding of how the port, intermodal trade, and the freight economy work, so they can see opportunity earlier and plan their future with better information.

That vision became a reality on February 24th at the Virginia Beach Convention Center. On that day, the entire seventh-grade class from every middle school in Virginia Beach, approximately 4,800 students, had the opportunity to experience the maritime supply chain in a way designed for them at Xpedition Port O Call . Many students walked in with only a vague idea of what the port does. They walked out understanding how goods move, who makes it happen, and what careers are waiting in their own region. This was more than an event. It is a blueprint for how education and industry can work together to strengthen Virginia’s future workforce.

Ryan Gilliland
Owner
Gilco Transport Services