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Gabrielle Winchester has a diverse work experience in marketing and branding. Gabrielle started their career as a Sales and Marketing Coordinator at Newport Beachside Resort in 2011, where they worked until 2014. In 2013, Gabrielle also worked as a Publicity/PR Associate at Jessica Wade Inc., where they organized press events and developed branding strategies for a new restaurant. From 2014 to 2016, they worked as a Marketing Specialist at Miami New Times, assisting local and global businesses in their marketing efforts.

In 2016, Gabrielle joined National Beverage Corp as a Social Media Specialist and later became a Social Media & Event Manager. Gabrielle then became a Brand Manager in 2018, staying with the company until 2019.

Gabrielle's most recent position was at Altadis U.S.A., where they held various roles in marketing. Gabrielle started as a Senior Brand Manager in 2019 and later became a Marketing Director in 2022. Their final position at the company was Senior Director of Marketing, which they held until 2023. In the same year, Gabrielle joined AFFCU as the VP of Marketing.

Gabrielle Winchester's education history began in 2004 when they attended Miami Springs Senior High School. Gabrielle graduated from high school in 2008. Following that, they pursued a Bachelor of Arts degree in Sociology and Communications at Florida International University from 2008 to 2012. After completing their undergraduate studies, Gabrielle enrolled at Nova Southeastern University in 2019 to pursue a Master of Business Administration (MBA) degree with a focus on Business, Management, Marketing, and Related Support Services. Gabrielle is expected to graduate in 2024.