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Stephen Gentry began their work experience in 1984 as a Director at Whirlpool Financial Corporation. In 1995, they joined Deutsche Financial Services as a Senior Vice President, holding the position until 2004. From 2004 to 2008, they worked as a Senior Vice President at N-1 Technologies. Stephen then moved to BankDirect Capital Finance in 2008, where they held the role of Sr. Executive Vice President & CFO.

Stephen Gentry attended Central Michigan University from 1976 to 1980, where they obtained a Bachelor of Science in Business Administration with a major in Accounting and a minor in Math. Stephen then went on to pursue a Master of Business Administration (MBA) with a finance concentration at Western Michigan University from 1982 to 1986.