Maddy is completing her JD at Osgoode Hall Law School. She honed her oral advocacy skills through case competitions while completing her MBA and further refined those skills while mooting in law school. In her final year at Osgoode, she will serve as a caseworker at Parkdale Community Legal Services on the social assistance, violence, and health team.

Maddy is particularly interested in tort law. As a research assistant to Professor Jason Neyers, she co-authored a critique of a recent UK Supreme Court decision on the tort of nuisance. She also worked under the supervision of Professor Alan Hutchinson, authoring a paper on Canadian court's approaches to awarding damages in claims of wrongful pregnancy.

Prior to attending law school, Maddy attained a Bachelor of Science and a Master of Business Administration from McMaster University. Maddy was deeply involved in advocating for issues pertaining to sports, particularly addressing gaps in accessibility for women and children with disabilities.