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Courtney Olive has held various roles in the professional world since 2014. Courtney began their career at Dude Solutions as a Client Success Representative, a role they held for three years. During that time, they also served as a Sales Support Representative, Account Manager, and Marketing & Sales Support. In 2017, they joined Wealth Access, Inc. as a Sales and Marketing Associate. In 2019, they moved to Fairygodboss, where they served as an Enterprise Brand Strategy Manager, Content Operations Manager, and Customer Success Manager. In 2022, they began their current role as a Customer Success Manager at Postal.

Courtney Olive obtained a Bachelor of Science (BS) in Fashion Textile Management from North Carolina State University between 2010 and 2014. In 2021, they obtained two additional certifications from LinkedIn: Diversity, Inclusion, and Belonging and Unconscious Bias.