Jennifer studied at the University of Toronto. She earned a B.A. (Honours) in Philosophy and Political Science in 1986 and an M.A. in Philosophy in 1987, taking a couple computer science courses along the way.

Jennifer considers philosophy a perfect background for writing about software: both disciplines require understanding and organization of complex systems of ideas.

After university Jennifer worked in the non-profit sector, first at B'nai Brith Canada, and later, after moving to Israel, at the Jerusalem Rubin Academy of Music and Dance. Jennifer lived for a few years on Kibbutz Ketura, where she worked in a variety of roles before moving to Tel Aviv and starting to work in software.

Jennifer moved back to Canada with her husband and son in 2002.