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Jessica O'Brien has worked in a variety of roles in the education sector. Jessica began their career in 2010 at National High School, where they served as the Assistant Director of Admissions. In 2014, they joined CeriFi as the Director of Sales - CFP Education and Review.

Jessica O'Brien has a Bachelor's degree in Business Administration (BBA) from Georgia State University, which they obtained in 2012. In 2018, they earned a Certificate in Digital Marketing from Columbia Business School and is currently pursuing a Master of Business Administration - MBA in Marketing from Southern New Hampshire University, which they expect to complete in 2020.