As enrollment increased in the 1960s and 1970s, Viewpoint included additional grades to meet demand and Viewpoint graduated its first senior class in 1982. This year, construction was also begun on Viewpoint's second academic building. Art O'Leary served as headmaster of Viewpoint from 1980 to 1986. Dr. Robert J. Dworkoski began his term on O'Leary's retirement in 1986. In June 2014, after 28 years as Headmaster, Dr. Dworkoski moved into the role of President of the Viewpoint Educational Foundation. During the 2014–15 school year, Paul Rosenbaum served as Interim Head of School. As of June 2015, Mark McKee is Head of School.