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Kevin Flanigan has worked in a variety of roles since 1998. Kevin began their career as an Advertising Director at Scene Magazine, where they sold print advertising to local businesses and managed a staff of sales executives. In 2002, they were an Account Executive at Village Voice Media, selling print advertising to Cleveland businesses. From 2003 to 2007, they held two roles in the City of Avon, Ohio: Councilmen at Large and Board Member of the Zoning Review Board. In 2007, they were a Market Development Executive at Raycom Media WOIO/WUAB TV Stations Cleveland, producing commercials, web, mobile, and social media campaigns. In 2013, they were a Medical Sales and Marketing Executive at ScleroTrainer® by Nelson Medical Enterprises, selling medical devices to hospitals, physicians, physician assistants, distributors, and nurses. In 2015, they were a Personal Banker at Huntington National Bank. From 2016 to 2017, they were a Sales Executive at Contempo Communications and a Partnership Development Manager at Cyrid Media.

Kevin Flanigan has a Communications degree from Baldwin Wallace University, obtained between 1991 and 1995. In 2016, they obtained a Health, Life & Accidential Ohio Insurance Licenses degree from Hondros College of Business. Kevin also holds a Real Estate License in the state of Ohio, obtained from Hondros College of Business in 2006. Additionally, Kevin holds seven certifications obtained from Google and The Trade Desk, obtained between 2020 and 2022.