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Madeleine Flanagan has a diverse work experience in the retail industry. Madeleine currently works as a Manager at Fable since March 2022. Before that, they worked at Aritzia from 2014 to 2020, starting as a Floor Manager and later becoming an Associate Manager. Prior to Aritzia, they worked at Michael Kors as a Sales Specialist and Sales Associate from 2013 to 2015. Madeleine'searliest retail experience was as a Sales Associate at Mendocino Clothing from 2012 to 2013.

Madeleine Flanagan pursued their Bachelor of Arts (B.A.) degree in History and English from Dalhousie University from 2011 to 2015. In 2021, they briefly attended Toronto Metropolitan University to study Human Resources Management. Prior to that, from 2020 to 2021, they were enrolled at George Brown College, where they focused on Business Administration and Management, General.