Writer educator, and lapsed curator, currently Professor of Arts Administration and Policy at the School of the Art Institute of Chicago. Weiss has published extensively on contemporary art in journals, magazines and newspapers in the US, Europe, Latin America, Asia and Australia.

Major publications include Making Art Global: The Third Havana Biennial (Afterall Books), To and From Utopia in the New Cuban Art (University of Minnesota Press), Por América: la obra de Juan Francisco Elso (Universidad Nacional Autónoma de México, Instituto de Investigaciones Estéticas: co-author and editor) and On Art, Artists, Latin America and Other Utopias by Luis Camnitzer (University of Texas Press: editor). Major curatorial projects include Global Conceptualism 1950s-1980s: Points of Origin (Queens Museum of Art, NYC: co-director with Luis Camnitzer and Jane Farver), Ante América (Biblioteca Luis Ángel Arango, Bogotá, and traveled in South, North and Central America: co-curator, with Gerardo Mosquera and Carolina Ponce de León), The Nearest Edge of the World: Art and Cuba Now (traveled throughout the US: co-curator with Gerardo Mosquera) and Imagining Antarctica (traveled throughout the US: funded by the National Science Foundation).