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Kerry Calderwood began their work experience in 1994 at The BaaN Company, where they served as the Senior VP Channels until 1999. After that, they joined PeopleSoft in 2001 as the Regional Vice President until 2004. In 2005, Kerry joined SAP as a Senior Account Executive, but their tenure ended in 2006. Kerry then worked at Rootstock Software from 2017 as the Regional Vice President. Currently, Kerry is working at Rimini Street since February 2019, serving as a Senior Account Executive.

Kerry Calderwood attended Brigham Young University from 1988 to 1990, where they earned a Bachelor's Degree in Communication and Media Studies.