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Kailey Ross began their work experience in 2009 as a Logistics Team Member at Alcon Laboratories, Inc. Kailey then held a Part-Time Brand Ambassador role at Mosaic Sales Solutions from October 2010 to May 2011. From May 2011 to May 2012, they worked as a Philanthropy Programs Coordinator (Internship) at Research In Motion. In 2014, they had an internship as a Revenue Management Team Member at Starwood Hotels & Resorts Worldwide, Inc. and also worked as a Sales and Marketing Coordinator at Noble Estates Wines & Spirits from August 2014 to April 2015. Kailey then worked as a Sales and Marketing Coordinator (Internship) at SpotJobs from November 2015 to May 2016. Kailey joined Sales Talent Agency, Inc. in September 2016 as a Sales Scout (Internship) and later became an Account Manager from January 2017 to March 2018. Kailey then progressed to a Senior Account Manager position from April 2018 to May 2019. From May 2019 to March 2021, Kailey worked as a Talent Acquisition Consultant at Scotiabank. Currently, they are employed at Tipalti, where they began as a Talent Acquisition Partner in April 2021. Kailey has since been promoted to a Talent Acquisition Manager and continues to work in that role starting from July 2023.

Kailey Ross completed their undergraduate education from 2009 to 2013 at McMaster University, where they pursued an Honors Commerce degree with a focus on Human Resources Management and Services. Following this, they attended Humber College in 2013 and 2014 to further their education in Hospitality and Tourism Operations Management, specializing in Hospitality Administration/Management. In 2014 and 2015, Kailey obtained the Level Three Award in Wine and Spirits from the Wine and Spirits Education Trust.