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Greg Flanagan's work experience begins in 1999 at SAIC, where they served as a Sr. Program Manager until 2000. From 2000 to 2006, they held the position of President at InfoAdvantage, Inc. / Xebec IT. Following that, from 2006 to 2007, they worked as a Chief Information Officer in Independent Consulting. Then, from 2007 to 2010, they served as Sr. Vice President & CIO at APS Healthcare. In 2010, they joined RegionalCare Hospital Partners as Vice President & CIO, a position they held until 2013. From 2013 onwards, they have been the Chief Operating Officer at AP Health, overseeing non-clinical functions. In 2014, they also had a brief stint as the Chief Information Officer at Coordinated Health.

Greg Flanagan received their Bachelor of Arts degree in Economics from Duke University in 1986. Greg then pursued a Master's Degree in Hospital Administration at the same institution, which they completed in 1988. Additionally, in 2011, they obtained the certification of Certified Healthcare CIO from CHIME.