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Jess Da Silva began their work experience as a Financial Analyst at Schneider Electric in 2006. They then went on to work as an Intermediate Staff Accountant at Fuller Landau from 2008 to 2010. In 2010, they joined Element Financial Corporation and held various roles including Controller, Assistant Treasurer, Vice President of Financial Accounting, and Vice President of Lease Accounting. From 2016, Jess served as the Vice President of Lease Accounting at ECN Capital.

From 2003 to 2007, Jess Da Silva pursued an Honours Bachelor of Business Administration degree with a specialization in Accounting at Wilfrid Laurier University.