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Richard Paolillo has several years of work experience in various roles. Richard currently serves as the Director of Licensing at Byte Federal, Inc. Richard previously worked as the National Sales and Marketing Director at Landshore Enterprises, LLC from 2017 to 2021. Prior to that, they were a Peer Advising Assistant at State College of Florida-Manatee-Sarasota from 2016 to 2017. Additionally, Richard served as a Contributor for the State of the U, a University of Miami athletics blog hosted by SB Nation and Vox Media, Inc. from 2013 to 2016. In this role, they covered a wide range of sports topics and also assisted in marketing and social media.

Richard Paolillo obtained their Associate of Arts degree in Business, Management, Marketing, and Related Support Services from the State College of Florida-Manatee-Sarasota, where they studied from 2013 to 2017. Richard then pursued a Bachelor's degree in the same field at the University of South Florida Sarasota-Manatee from 2017 to 2021.

In addition to their formal education, Richard Paolillo has obtained several certifications. In June 2021, they became a Certified FlexMSE Installer through Trexiana - Flex MSE. In February 2021, they completed Stormwater Training at the University of South Florida. In September 2020, they received the Florida HOA Director DBPR Certification from the Florida Department of Business and Professional Regulation. In September 2018, they became a Qualified Stormwater Management Inspector through the Florida Department of Environmental Protection. Furthermore, they earned the Inbound Marketing Certified and Inbound Sales Certified designations from HubSpot Academy in October 2019. Finally, in October 2017, they became a Notary Public for the State of Florida.