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Jessica T. has a diverse work experience, starting in 2011 as a Receptionist and Administrator at the Royal Canadian Yacht Club. In 2012, they worked as a Customer Service Representative/Receptionist at La Capitale and also began working as a Tutor at TutorBright. In 2013, they joined Provident Energy Management Inc. as a Billing & Collections Administrator. From 2014 to 2018, Jessica worked as a Customer Service Representative at Alectra. In 2017, they had a placement as a Paralegal student at Legal Aid Ontario and later joined the company in 2018 in various roles, including Client Service Centre Representative and Client Service Centre Specialist. Overall, Jessica has gained experience in customer service, administration, tutoring, and legal aid work.

Jessica T. started their education in 2005 at St. Ignatius of Loyola, where they obtained their OSSD degree in 2009. In 2009, they enrolled at the University of Toronto - Victoria University and pursued an Honours Bachelor of Arts degree until 2014, though their field of study is unspecified. Jessica later attended Sheridan College from 2016 to 2017, where they completed a Paralegal program specializing in Law. In November 2017, Jessica obtained their Licensed Paralegal certification from The Law Society of Upper Canada.