The position of Superintendent of Mount Vernon, also called "Secretary" in the earlier years of the Mount Vernon Ladies' Association, was created in 1860 when Colonel Upton Herbert was hired. A veteran of the Mexican War, Herbert was recommended by John Augustine Washington III as being especially suited to assisting the MVLA. Mr. Herbert and Sarah Tracy, Secretary to Ann Pamela Cunningham, were largely responsible for the care and maintenance of Mount Vernon during the Civil War when the Regent and most Vice Regents were unable to travel to the estate. When hiring a new Superintendent, J. McHenry Hollingsworth in 1872, the Council explained the responsibilities of the Superintendent more thoroughly saying he "should act as general manager of the estate; that one of the most important features in the general instructions to be given him shall be, that he shall at all times consider the dignity and comfort of the Regent; that he shall always bear in mind the deep obligations of the Association to her; and that he has been appointed for the purpose of relieving her of the very arduous duties that are so oppressive to her; that he shall keep the accounts of expenditures and receipts, which are to be at all times open to the inspection of the Regent, Vice Regents, and Advisory Committee, with whom, in all matters of perplexity, he shall consult, and be guided by their decisions." His salary was to be $1500 per year.

After discovering decay in the foundations of the Mansion in 1885, the Vice Regents suspected negligence on the part of Hollingsworth. The Vice Regent from Georgia, Mrs. Eve questioned, "Would it be too much to say that the first and greatest duty of the Superintendent is the preservation of the Mansion?" The Council went on to pass a resolution stating that the duty of the Superintendent is to examine all parts of the Mansion and report defects to the Regent, and concluded that he should "not at any time be ignorant of the state of the mansion." Harrison H. Dodge was hired later that year and remains the longest serving Superintendent (or equivalent) of Mount Vernon at 52 years. Mr. Dodge's priority was cleaning, restoring, and preserving the house and grounds. He was also particularly interested in fire safety, advocating for the installation of electricity in the Mansion to prevent any accidents from candlelight or kerosene lamps.

After Dodge's death in 1937, his assistant Charles C. Wall became the new Superintendent and later changed the position's title to Resident Director. Wall described the Superintendent's job in a book he coauthored with Gerald W. Johnson entitled Mount Vernon: The Story of a Shrine, saying the position required someone "not exactly a farmer, yet a man acquainted with soils, seasons, and the proper handling of growing plants." He went on to say the director should have traits of a theatrical producer, an accountant, an antiquarian, a historian, and an ambassador, with some knowledge of engineering, carpentry, masonry, and domestic service. Wall also spent almost his entire career at Mount Vernon, retiring in 1976 after 43 years of employment at Mount Vernon. He is credited with impeccable hospitality of numerous VIP guests, overseeing major building and restoration projects, such as the reconstruction of the Greenhouse, and guiding the Estate through the years of World War II and other periods when visitation was down. He wrote extensively on George Washington and Mount Vernon, including several publications as well as internal reports and essays.

The next two decades saw four different but distinguished Directors who all brought their own gifts and talents to the position. Harrison Symmes replaced Charles Wall as Resident Director in January 1977. A World War II veteran, Symmes had also served as an Ambassador to Jordan and as President of Windham College in Vermont. Although he resigned in 1979 after only 2 ½ years in the position, he was credited by his Assistant Director, John A. Castellani, as someone who "opened the doors to a new era of reevaluation, exploration, and change." Mr. Castellani succeeded Symmes as Resident Director and stayed in that role until 1984. His focus was largely on fundraising as he successfully guided Mount Vernon through a Capital Campaign effort to build a new administration and research facility on the grounds, the Ann Pamela Cunningham Building. John E. Harbour served in the position from 1984 to 1987 after several previous directorships at historic sites and museums. Harbour worked to improve research access to historic collections and update interpretation of museum exhibits. He helped implement a reorganization plan at Mount Vernon, creating a Research Department and expanding the roles of other departments including Education, Curatorial, Library, and Development. Harbour also wrote the "Report on the Recommended Improvements to the Museum, Museum Annex and Outbuildings" in 1986. Several major accomplishments marked the tenure of Neil W. Horstman, Resident Director from 1987 to 1994, including the Historic Structures Report, the first stages of the Pioneer Farm project, and the Piscataway Park Expansion.

The Superintendents and Resident Directors have continuously lived on the grounds at Mount Vernon. Harrison Dodge stayed on the second floor of the Office Dependency (now called the Servant's Hall), with his office on the ground floor. His family lived at their home in Georgetown and he often went home on the weekends. When the Administration Building (now the Frances P. Bolton Building) was constructed, he moved into quarters on the ground floor along with his assistant, James Young. A new residence was built in 1936 for Charles Cecil Wall after he had assumed the role of Assistant Superintendent, to accommodate him and his family. This house has remained the residence for each succeeding Resident Director or President, CEO, and has undergone multiple upgrades and renovations.