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Kennedy Keaton began their work experience in 2018 as a Sales Development Representative at Chili Piper. In this role, they worked from June 2018 to December 2019. They then joined Wingmate in February 2020 as a Business Development Representative, where they are currently employed. At Wingmate, Kennedy is responsible for engaging field staff to drive growth, efficiency, and open communication with the team at the office.

Kennedy Keaton attended the Smith School of Business at Queen's University from 2015 to 2018. During this time, Kennedy pursued a Bachelor of Commerce (BCom) degree with a focus on Business/Commerce, General.