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Jeffrey Leman has a diverse range of work experience. Jeffrey began their career as an Assistant Vice President at Crum & Forster Managers Corp. in 1981 and remained in the role until 1986. From there, they joined INEX Insurance Exchange as Vice President of Operations & Treasurer, where they worked until 2000. In 2000, they became the Chief Operating Officer at The Cochlan Group, Inc., and held the position until 2006. That same year, they joined Prime Insurance Company as Chief Operating Officer, E.V.P. of Underwriting, and Corporate Secretary. In 2010, they became a Director at Resolution Horse Company and continued in that role until 2015. From 2014 to 2017, they also served as a Board Member at Intermountain Christian School.

Jeffrey Leman pursued their education starting in 1978, when they enrolled in the Gies College of Business at the University of Illinois Urbana-Champaign. Jeffrey obtained their Bachelor's Degree in Finance, with a specialization in Banking and Investment in 1981. Following this, from 1983 to 1985, Jeffrey attended DePaul University, where they received their Master of Business Administration (MBA) with a focus on Finance.