After dropping out of high school, Jacob's first play was produced by Edward Albee at Stages Repertory Theatre in Houston. Since then, his plays were produced in Chicago, Austin, Minneapolis, and Portland, Oregon. He is a Network Playwright at Chicago Dramatists, a member of the Dramatists' Guild, and the Resident Playwright at Uptown Chicago's only theatre for development, Scrap Mettle SOUL. His play, Kantor! Kantor! is currently being considered by Tadeusz Kantor's Polish state archive for publication; and Under America, his latest script, was one of five selected by the Driehaus Foundation for potential workshops by the Sundance Institute.

Recipient of multiple academic and playwriting honors including a Diedrich & Johnson Scholarship at Northwestern University, a Lee Blessing Scholarship to attend the Timberlake Writers' Colony, and a Tennessee Williams Scholarship to attend the Sewanee Writers' Conference, Jacob teaches theatre history and an honors seminar at the University of Illinois, Chicago (UIC); he is also the current faculty liaison for Chicago Circle Players, UIC's independent, student-run theatre organization. He trained as a playwright with Edward Albee at the University of Houston and attended Clackamas Community College (A.A. 1996), Reed College (B.A. 1999) and Northwestern University (Ph.D. 2007). He taught at Northwestern University (2002-2007), and began teaching at UIC in 2005. In addition, he teaches writing at the School of the Art Institute, Chicago.

His chapter "Repairing Reality: The Media and Homebody/Kabul in New York, 2001" appeared in Tony Kushner: New Essays on the Art and Politics of the Plays, and, in 2008, the volume "We Will Be Citizens": New Essays on Gay and Lesbian Drama will include his contribution: "Mainstream Theatre, Mass Media, and the 1985 Premiere of The Normal Heart: Negotiating Forces Between Emergent and Dominant Ideologies." He has presented at many national and international conferences garnering the Graduate Student Debut Award from the American Theatre and Drama Society (2002), and the Literary Managers and Dramaturgs Association Debut Panel Award (2005), both at Association for Theatre in Higher Education conferences.