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Cory Cumming has a diverse work experience background. In 2013, they worked as a General Labourer at Ross Steel Fabricators & Contractors. Starting in 2014, Cory worked as a Meat Cutter at Heidi's Independent Grocer until 2019. In 2017, they became a Student Ambassador for the Law Clerk Program at Lambton College, where they represented and promoted the program. Cory also had work experience as a Summer Student at Legal Aid Ontario in 2018, and later that year, they worked briefly as a Law Clerk at Fleck Law. Currently, Cory holds the position of a Legal Aid Worker at Legal Aid Ontario.

Cory Cumming attended Lambton College from 2016 to 2018, where they studied Law Clerk. During their time at Lambton College, they obtained additional certifications including IASR - Human Rights Training in March 2017, Workplace Violence Training in March 2017, Bringing In The Bystander in October 2016, and Worker Health & Safety Awareness in September 2016. Additionally, they completed Nonviolent Crisis Intervention training from the Crisis Prevention Institute in February 2017. Prior to attending Lambton College, Cory Cumming also pursued a degree in Music Industry Arts at Fanshawe College, although the specific duration of this program is not provided.