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Kelly O'Bray has a diverse work experience spanning over several years. Kelly began their career at MTS Allstream in 1984 as a Marketing Manager before moving on to All Sport Ventures in 2000, where they served as a Partner and VP of Marketing. In 2004, they joined HR Adworks as a Sales and Marketing Manager and successfully grew revenue by over 100% in two years. Kelly then joined LogicNow in 2007 as a Community Manager, where they stayed until 2017.

Starting in 2017, Kelly joined RAPID RTC as a Director of Dealer Sales & Service, and then as a Senior Director of Dealer Sales and Support, overseeing sales and support operations. In 2020, they joined Eptura as the Director of Customer Success and continued to hold this role in 2022. Their work experience demonstrates a diverse background in marketing, sales, and customer success.

Kelly O'Bray attended the University of Manitoba from 1990 to 1994, where they received a CIM degree in Management and Marketing. From 2003 to 2004, they attended Red River College Polytechnic, and from 2006 to 2011, they enrolled in the International Sommeliers Guild.