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Matthew O'Keefe has worked in various roles in the technology industry since 1998. Matthew began their career as a Senior Implementation Manager at CareTools, Inc., followed by a role as Regional Business Manager at UMS United Medical Systems in 2002. In 2006, they took on a Business Development role at Allscripts, and then moved to Satuit Technologies in 2008, where they were Assistant VP Sales. In 2009, they became Director of Operations and Business Development at Turbo-Leads.com/US Auto Plex. Matthew then worked at AppMatrix Inc. as a Senior Account Executive from 2011 to 2013. From 2013 to 2018, they were VP Business Development at OpenMobile World Wide, Inc. and then Head of Sales and Business Development, North America at Flexion Mobile Plc. Most recently, they have been a Strategic Account Executive at Tipalti since 2020 and an Account Executive at PayEm since 2021.

Matthew O'Keefe attended Silver Lake Regional High School from 1987 to 1991, after which they obtained a Bachelor's degree in Psychology from Saint Michael's College between 1991 and 1995.