Dr. Otero-Pailos teaches graduate courses on architectural history, theory, and historic preservation at Columbia University in New York, where he as been a full time professor since 2002. Prior to his current appointment, he was a founding faculty member of the New School of Architecture in San Juan, Puerto Rico.

Otero-Pailos' teaching and research interests include modernism and postmodernism in architecture, the relationship between historical research and creative design interventions, the history of avant-garde and rear-garde practices, aesthetic philosophy, early modern and modern theories of perception, and contemporary historiography. He teaches graduate seminars that cut across these areas, such as "The Concept of Authenticity: Contestations between Architecture and Preservation," and "The Phenomenological Project in Architecture: From Hermeneutic Ontology to Existentialism." Otero-Pailos also teaches the graduate survey sequence in "The History of American Architecture," I (Before 1876) and II (1876-1989), and the required two-semester core "Preservation Studio." These courses stake out a pedagogy that contests the denotative stability of historical artifacts and encourages students, through intellectual exercises such as class debates, to creatively intervene in the past as a way to invent the new. At the heart of Otero-Pailos' wide range of interests is a deep concern for understanding the past as a provocation, not a constraint, to contemporary modes of architectural and intellectual production. To this end, he founded Future Anterior: Journal of Historic Preservation History, Theory and Criticism, the first and only such publication in American academia to advance the critical examination of this expanding discipline. The journal seeks to bring together theoretical and critical work from multiple disciplines where research into historical preconditions spurs design innovation. Prior to joining Columbia, Otero-Pailos was Assistant Professor of Architecture and a founding member of the New School of Architecture at the Polytechnic University of Puerto Rico, where he was responsible for developing the School's Theory of Architecture curriculum and for teaching architectural design studios. He is the Secretary of DoCoMoMo's US National Board.