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Cal Thompson's work experience includes various roles in different companies. Cal started their career as an intern at the National Basketball Retired Players Association in 2011. Later, they worked as a basketball coach at Orangewood Christian School from 2009 to 2012. In 2012, Cal had internships at the Florida Basketball Association and Rogers Benefit Group. Cal also served as the General Manager at Florida Flight from 2012 to 2013. Cal joined Principal Financial Group in 2016 as a Financial Representative, where they provided advisory services and sold insurance products until 2023. Cal then worked as the President of Sync Insurance from 2014 to the present. Currently, Cal is the Vice President of Employee Benefits at Sihle Insurance Group, starting in 2023.

Cal Thompson attended the University of Central Florida from 2009 to 2013, where they earned a Bachelor of Business Administration (B.B.A.) degree with a focus on Finance, General. In addition to their degree, they obtained certifications in Series 6 from the Financial Industry Regulatory Authority (FINRA) in May 2016 and in 215 - Health, Life and Variable Annuities from the Florida Department of Financial Services in October 2013.