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Rachael Taylor Benjamin has extensive work experience, starting in 2010 as the Director of Sales and Box Office for the Arts Undergraduate Theatre Society. Rachael Taylor then worked as a Sales Associate at Chateau de Paraza before becoming the Production Manager for Tuesday Night Theatre. Rachael Taylor also worked as an After-School Drama Instructor at The Akiva School and as the Director/Co-Producer for VDAY McGill. In 2013, they interned as an Influencer Outreach Intern for Girl Rising. From 2014 to 2016, they served as the Office Manager & Executive Assistant at The Documentary Group. Rachael Taylor then joined Judy Henderson Casting as a Casting Assistant for a few months in 2016. From 2016 to 2021, they worked at Showtime Networks Inc., where they held various roles, including Assistant to Directing-Producer on HOMELAND, Assistant to the Line Producer on BILLIONS, and finally as an Associate Producer on BILLIONS. Currently, as of 2021, they are the Director of Brand Integration at BENlabs.

Rachael Taylor Benjamin attended McGill University from 2008 to 2012, where they earned a Bachelor of Arts (B.A.) degree. Their major field of study was English and Theatre Studies, as well as English, Drama, and Theatre.