Prior to joining the University of Toronto, Masoud was a Lecturer in Landscape Architecture and Urban Design at the Department of Urban Studies and Planning at the Massachusetts Institute of Technology (MIT), and a Research Associate affiliated with the MIT Norman B. Leventhal Center for Advanced Urbanism where he directed various research and design projects. Masoud also held faculty and research appointments at the Harvard Graduate School of Design, where he taught design studios and seminars on urbanism, landscape, and visual representation.