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Josh Rainey has worked in various roles and companies throughout their career. In 2002, they began their career at Ernst & Young, where they worked in Assurance and Advisory Business Services until 2004. From 2004 to 2008, they worked at HSI as a Manager. In 2008, they joined NextGen Healthcare Information Systems as a Sr. Account Manager for NextGen RCM Services, where they stayed until 2017. In 2018, they joined Experity as the Director of Client Success and later became the Vice President of Client Success in 2023.

Josh Rainey earned a Master of Business Administration (M.B.A.) degree in Accounting from Indiana University Bloomington in 2001-2002. Prior to that, they obtained a Bachelor of Science (BS) degree in Accounting from the same university, which they completed in 1997-2001. Additionally, Josh Rainey also obtained the Certified Public Accountant certification in September 2006.