Madeleine summered and articled at the firm, where she gained experience in a wide range of practice areas. Prior to rejoining the firm, Madeleine clerked at the Court of Appeal for Ontario.

Madeleine graduated from the University of Toronto Faculty of Law. Throughout law school, Madeleine worked and volunteered in the refugee and immigration division of Downtown Legal Services, as well as the David Asper Centre for Constitutional Rights as a working group leader. Madeleine was also extensively involved in the mooting program, including as a participant in the Grand Moot and the Callaghan Cup where her team won first place overall and where she received the Best Oralist prize.

Madeleine holds a Bachelor of Arts from McGill University, where she graduated with distinction. Before attending law school, Madeleine worked for two years in international organizations, with a focus on advocacy in a variety of United Nations fora.