VIRGINIA BEACH, VA, September 28, 2026 /24-7PressRelease/ -- Ryan W. Gilliland has been selected for inclusion in Marquis Who's Who. As in all Marquis Who's Who biographical volumes, individuals profiled are selected on the basis of current reference value. Factors such as position, noteworthy accomplishments, visibility, and prominence in a field are all taken into account during the selection process.

Mr. Gilliland's professional journey reflects a deep commitment to strengthening the transportation and maritime industries throughout Hampton Roads and the Commonwealth of Virginia. Since 2025, he has served as Second Vice President and an officer on the Board of Directors of the Tidewater Motor Truck Association (TMTA), where he plays an active role in advancing the association's mission of representing the region's motor carrier community while promoting safety, education, operational efficiency, and industry collaboration. His involvement extends beyond traditional board responsibilities and includes organizing industry networking and educational events, supporting charitable initiatives, engaging with Port of Virginia leadership and stakeholders, and helping create opportunities for meaningful dialogue between motor carriers and the maritime partners they interact with every day. Through these efforts, Mr. Gilliland has worked to strengthen relationships across the transportation community and ensure that the concerns, experiences, and perspectives of local motor carriers have a meaningful voice in conversations affecting the broader maritime industry.

Since 2021, Mr. Gilliland has also served as the founder, owner, and lead instructor of Gilco Transport Services, a commercial driver training academy based in Portsmouth, Virginia. The school was established following an extensive two-year process of industry research, regulatory review, proposal development, and curriculum design, to create a training program that prepared students not simply to pass a CDL examination, but to become safe, capable, and employable professional drivers.

Drawing inspiration from his family's longstanding involvement in the transportation industry, particularly his grandmother, Shirley Roebuck, who founded Gilco Trucking in 1975, Mr. Gilliland developed a training philosophy centered on comprehensive instruction, hands-on experience, and long-term safety. The academy provides Class A and Class B CDL training, Entry-Level Driver Training (ELDT), endorsement instruction, refresher training, and customized programs for individuals and employers. By combining classroom education with extensive behind-the-wheel instruction and practical knowledge gained from operating within the trucking industry, Mr. Gilliland has worked to bridge the gap between obtaining a commercial driver's license and developing the skills, judgment, and professionalism necessary for a successful career in transportation.

Gilco Transport Services is distinguished by its small class sizes — limited to four students per session — and a month-long training period designed to ensure that each graduate is fully prepared for the demands of commercial driving. Mr. Gilliland personally teaches class A and class B commercial driver's license courses, hazardous materials theory, tank theory and retraining sessions for both new entrants and experienced drivers who require refreshers. To augment his qualifications, he is certified and licensed as a commercial driving trainer by the State of Virginia and recognized as a certified trainer provider by the Federal Motor Carrier Safety Administration.

In addition to his work as an instructor and business owner, Mr. Gilliland remains actively involved in the daily operations of Gilco Trucking. This third-generation family business has served the Hampton Roads transportation community since 1975. He works alongside his mother, Stacey Gilliland; his father, David Bolen; his brothers, Chuckie and Tony Bolen; and a dedicated, long-serving office staff to oversee a fleet of approximately 50 power units supporting the Port of Virginia and customers throughout Virginia and the surrounding region.

His responsibilities span both operational and administrative functions, including addressing day-to-day challenges, supporting dispatch and fleet operations, maintaining regulatory and safety standards, managing customer and industry relationships, and helping guide the company as the transportation industry continues to evolve. As a company deeply rooted in port-related trucking, Gilco has developed extensive experience in the intermodal sector, including approximately a decade serving as a house carrier supporting the Port of Virginia's rail operations. Mr. Gilliland's involvement in the family business provides him with a firsthand understanding of the challenges facing motor carriers, drivers, and port stakeholders, an experience that directly informs his broader work in industry advocacy, education, and maritime leadership.

Prior to assuming his current leadership roles, Mr. Gilliland gained valuable hands-on experience as a crane operator with Crofton Industries, a maritime construction company, from 2014 to 2020. During his six years with Crofton, he developed technical skills and firsthand knowledge of marine and port operations while also gaining a deeper understanding of the day-to-day realities of doing business within the maritime industry. Just as importantly, this experience allowed him to begin building relationships across the maritime community and taught him the value of collaboration, communication, and strong industry partnerships, lessons that continue to influence his approach to leadership today.

Earlier in his journey, Mr. Gilliland served in the United States Army as a Cavalry Scout, beginning his military service in 2005 and later deploying to Iraq in 2007. His service included supporting route-clearance and convoy operations in a demanding environment where preparation, accountability, teamwork, and the ability to make decisions under pressure were essential. The experience became an important foundation for his development as a leader, instilling a sense of resilience, determination, and responsibility to those around him. Those lessons continue to influence his approach to business and industry leadership today, particularly his willingness to take responsibility, confront difficult challenges directly, and remain committed to serving both his industry and the broader maritime community.

Mr. Gilliland's commitment to the transportation and maritime industries extends well beyond his family businesses through active leadership, advocacy, and service across several of Hampton Roads' leading industry organizations. Since 2026, he has served as Vice Chair of the Port of Virginia's Motor Carrier Committee, where he helps provide a direct forum for the motor carrier community to communicate operational concerns, identify recurring challenges, and work collaboratively with Port leadership toward practical solutions that improve safety, efficiency, and the day-to-day experience of drivers and carriers serving Virginia's marine terminals.

He also serves on the Board of Governors of the Propeller Club, Port of Norfolk, an organization dedicated to promoting and supporting the broader maritime community. Through networking, educational, and industry events, the organization brings together professionals from across the maritime sector while also raising funds that are returned to the community by supporting local and regional charitable organizations. Mr. Gilliland's involvement reflects his belief that the strength of Hampton Roads' maritime industry should also contribute to the strength of the community that supports it.

Mr. Gilliland is also an active member of the Virginia Maritime Association (VMA), serving on both its Inland Transportation and Workforce Development Committees. His participation allows him to contribute perspectives shaped by his experience as a motor carrier, business operator, and commercial driver educator while working alongside representatives from across the maritime supply chain. Through these roles, he has increasingly focused on strengthening communication among different sectors of the industry, developing the region's future workforce, and ensuring that the motor carrier community has a meaningful voice in conversations that affect the movement of freight through the Port of Virginia and the greater Hampton Roads region.

Dedicated to continuous professional and personal growth, Mr. Gilliland completed the Virginia Maritime Association's Maritime Leadership Certification Program in 2025, further broadening his understanding of the interconnected businesses, organizations, and infrastructure that make Hampton Roads one of the nation's most important maritime and transportation regions. The experience complemented the knowledge gained throughout his career by exposing him to perspectives from across the maritime supply chain and reinforcing the importance of collaboration among the many industries that depend upon the Port of Virginia.

Mr. Gilliland attributes much of his drive and leadership philosophy to an upbringing deeply rooted in trucking, family, and service. Raised under the influence of strong Southern women, particularly his grandmother, Shirley Roebuck, and his mother, Stacey Gilliland, he learned early the importance of perseverance, discipline, personal responsibility, and treating people with respect. Those values were further strengthened through his service in the United States Army and later through the responsibilities of helping carry a third-generation family business into its next chapter.

Today, those experiences have shaped a leadership philosophy centered on service, relationship-building, and creating opportunities for others. Whether training the next generation of professional drivers, advocating for the motor carrier community, supporting workforce development efforts, or bringing together different segments of the maritime industry, Mr. Gilliland remains focused on strengthening the industry that helped shape him. His long-term goal is not simply to continue his family's legacy, but to build upon it by helping ensure that Hampton Roads remains a place where transportation and maritime businesses, their employees, and the communities that depend upon them can continue to grow and prosper.

Helping others and creating opportunities for the next generation are also central to Mr. Gilliland's involvement in the Hampton Roads community. In addition to the charitable efforts supported by the Propeller Club and the Port of Norfolk, and his involvement with the Virginia Maritime Association, he has participated in workforce development initiatives with public schools throughout Virginia Beach, Chesapeake, Newport News, and the surrounding region. Through career fairs, educational programs, and direct engagement with students, he works to introduce young people to careers in trucking, transportation, logistics, and the maritime industry, particularly the many paths beyond the more visible jobs traditionally associated with the Port of Virginia. As both an employer and commercial driver educator, Mr. Gilliland believes that strengthening the region's future workforce begins with exposing students to these opportunities early and connecting education with the real-world needs of industry.

Outside of his professional and civic commitments, Mr. Gilliland enjoys spending time outdoors, whether camping, driving the beaches and mountain trails, or spending time on the water. He also enjoys working on projects around his home, experiences that provide a hands-on balance to a professional life largely centered around business, transportation, and community involvement.

Looking toward the future, Mr. Gilliland hopes to continue expanding his leadership and service within the organizations and industries that have played such an important role in his life. Inspired by his grandmother, Shirley Roebuck, he aspires to take on greater leadership responsibilities within organizations such as the Tidewater Motor Truck Association, the Virginia Maritime Association, and the Propeller Club, Port of Norfolk. His ambitions, however, extend beyond holding a particular title. At their core is a desire to help strengthen the connections between trucking, maritime commerce, workforce development, and the communities of Hampton Roads.

For Mr. Gilliland, that work represents both a continuation and an evolution of his family's legacy. From a trucking company founded by his grandmother in 1975, to military service, maritime construction, commercial driver education, business leadership, and industry advocacy, each chapter has contributed to a broader commitment to service and progress. As he looks ahead, he remains focused on continuing to learn, building meaningful relationships, creating opportunities for others, and leaving the transportation and maritime community of Hampton Roads stronger than he found it.

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