Upon completing his B.S. degree from Columbia, Massimino worked for IBM as a systems Engineer in New York City from 1984 until 1986. In 1986 he entered graduate school at the Massachusetts Institute of Technology where he conducted research on human operator control of space robotics systems in the MIT Mechanical Engineering Department's Human-machine systems Laboratory. His work resulted in the awarding of two patents. While a student at MIT he worked during the summer of 1987 as a general Engineer at NASA Headquarters in the Office of Aeronautics and Space Technology, during the summers of 1988 and 1989 as a research fellow in the Man-Systems Integration Branch at the NASA Marshall Space FLIGHT Center, and during the summer of 1990 as a visiting research Engineer at the German Aerospace Center (DLR) in Oberpfaffenhofen, Germany. After graduating from MIT in 1992, Massimino worked at McDonnell Douglas Aerospace in Houston, Texas as a research Engineer where he developed laptop computer displays to assist operators of the Space Shuttle remote manipulator system. These displays included the Manipulator Position Display, which was evaluated on STS-69. From 1992 to 1995 he was also an adjunct assistant professor in the Mechanical Engineering & Material Sciences Department at Rice University, where he taught feedback control of mechanical systems. In September 1995, Massimino joined the faculty of the Georgia Institute of Technology as an assistant professor in the School of Industrial and Systems Engineering. At Georgia Tech he taught human-machine systems engineering classes and conducted research on human-machine interfaces for space and aircraft systems in the Center for Human-Machine Systems Research, and is currently an Adjunct Assistant Professor at Georgia Tech. He has published papers in technical journals and in the proceedings of technical conferences. In 2011, Massimino co-hosted season three of National Geographic Channel's Known Universe documentary series along with Sigrid Close, Andy Howell, David E. Kaplan, and Steve Jacobs.