After graduating from Georgetown University with an interdisciplinary major in philosophy, English and women's studies in 1990, Jenny Toomey co-ran Simple Machines, an independent record label, for eight years with Kristin Thomson. Among Simple Machines' more than 70 releases was the 24-page Mechanic's Guide to Putting Out Records, which described a do-it-yourself process for producing records and CDs while educating young artists about the value of retaining control of their work. The guide helped to launch a number of independent labels and led to somewhat of a DIY renaissance in the alternative music community throughout the 1990s.

Toomey has been a composer and performer on at least 12 CDs and dozens of compilation records, singles and a musical. The records were released on Simple Machines and other independent labels, including Homestead, Sub Pop and 4AD. Her solo CDs, Antidote and Tempting, were released on Misra Records in the early 2000s.

After closing down Simple Machines in 1998, Toomey worked for three years at The Washington Post as a copywriter. She also wrote music and technology reviews for the Post, the Village Voice, CNET and a variety of other music and technology publications.
She is the executive director of the Future of Music Coalition, which claims a mission of bringing together the worlds of music, technology and public policy, especially as they relate to copyright law.