Leesburg, VA (July 31, 2026) – Orland “OJ” Jackson, a 26-year Town employee, is retiring. 

OJ joined Town staff in February 2000 as the Superintendent of Streets, Buildings, and Grounds for the Town’s Public Works Department. When oversight of Building Maintenance became its own position in 2006, OJ  became Streets Superintendent, a position he has held until his retirement.

As Streets Superintendent, OJ supervises a staff of 30 that are responsible for keeping Leesburg’s 269 lane miles clean and maintained. His division oversees ongoing maintenance; a work order system for tasks throughout Town that require attention; brush and leaf collection; sign repairs; and special projects. Public Works also works during all Town and some permitted special events and is responsible for hanging the American flags during certain times of the year.

To OJ, his greatest responsibility has been in delivering superior customer service to Town residents, remaining responsive to customer expectations. He also prides himself on the employee development he has been able to oversee, always working to train his employees up for the next position and promote from within whenever possible.

In addition to his service to the Town, OJ also proudly served the nation as a 20-year member of the U.S. Army, retiring in December 2003 as a Sergeant First Class E7. As a reservist during his two decades in the military, O.J. was stationed in Saudi Arabia during Operation Desert Storm/Desert Shield from 1990-91. He was activated again in 2002 and was stationed for a year in Fort Lewis, Washington, for Operation Noble Eagle.

Prior to joining Town staff, OJ spent 17 years in the private sector in the construction industry.

“What started as a job became a career. More importantly, a lot of my co-workers have become great friends and are like a second family,” OJ said. “Over the years we have worked through every kind of weather imaginable and more emergency callouts than I can count. We all worked long hours, solved problems together, and did whatever it took to keep our streets safe and our community moving. Street maintenance work is not always easy, and it is not always noticed, but it matters. Every repaired road, every clear street, every late-night response, every special event all made a difference to someone living in this community.”

“It’s been an honor to work with OJ and to see the positive impact he has had on Leesburg,” stated Public Works Director Renee LaFollette. “The depth and breadth of OJ’s experience in construction and maintenance, not to mention the leadership skills gained from his military service, have been well used and put to the test in his years with the Town.”

In retirement, OJ said he is looking forward to traveling with his wife—with several trips already planned—and having time to work on some home improvements.

Media Contact: 
Kara Rodriguez, Public Information Officer 
pio@leesburgva.gov Ÿ 703-669-1425