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Jaimie Small began their work experience in 2016 as the Founder and CEO of 2i Media. In 2022, they joined the Portland Trail Blazers @ the Rose Quarter as an Executive Assistant to the Chief Communications & Impact Officer. Later in the year, they took on the role of Co-Chair in the Black Employee Network. In 2023, Jaimie became a Project Manager and Executive Assistant to the Chief People & Impact Officer at the same company.

Jaimie Small attended The University of South Carolina but did not include information about the start and end years or any specific degree or field of study.