His great-great grandfather, Hugh Dobbin, was minister and headmaster at Patterson for 23 years. Jesse grew up in Happy Valley, and spent his free time in the mountains behind the central campus. He and his family continue to farm much of the land to the west of Patterson School. Jesse attended high school at the North Carolina School of Science and Mathematics, and was awarded a BS in Biology from Dartmouth College in 1995. He went on to receive a Masters in Architecture from the University of Virginia in 1999. Jesse is also the Chair of the Board of the Chapel of Rest Preservation Society, charged with the stewardship of the former chapel for the Patterson School. As an architect, Jesse is particularly focused on the restoration and preservation of the numerous buildings on campus. Current projects include the restoration of Palmyra Hall.