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Jesse Spear has worked in a variety of roles in the marketing and sales field. From 2010 to 2015, they worked as an Assistant Tennis Shop Manager at the Piping Rock Club during the summer months. In 2015, they took on a Summer Intern role at Boyarski Fritz, LLP. In 2016, they worked as a Digital Marketing Intern at Leviton. In 2017, they worked as a Social Media Marketing Consultant at MYX Beverage, LLC. In 2018, they worked as a Sales and Marketing Intern at Morph Hospitality Group and held various roles at redpepper, including Marketing Apprentice, Media & Content Marketing Strategist, Marketing Manager, and Senior Marketing Manager.

Jesse Spear obtained a Bachelor of Arts in Media Studies and Spanish from the University of Virginia in 2017. Prior to that, they were an International Baccalaureate Diploma Recipient from Locust Valley High School in 2013. Jesse then went on to pursue a Master's degree in Marketing from Vanderbilt University - Owen Graduate School of Management in 2018.