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Kevin Sullivan started their career in 2005 as the owner of RuckingInsurance.com. Kevin then co-founded the Try Donation Program in 2010, collecting used rugby gear and jerseys for youth teams in need. In 2014, they became a professional advisor and owner at Connor, Alexander and Sullivan Insurance Services, where their mission was to ensure clients' insurance needs were met. In 2016, they took on multiple roles, including PNP Insurtech Advisor at Plug and Play Tech Center, advising members on insurance monetization and reaching decision makers, and VP of Insurance at Safesite - Real-Time Risk Intelligence.

Kevin Sullivan obtained a Bachelor of Science degree in Physics & Math from the University of Scranton from 1988 to 1990. In addition, they attended the University of Oklahoma at some point, but no specific information regarding their degree or field of study is provided.