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Josh Raimondi has worked in various roles across multiple companies. In 2002, they began their career at Xerox Corporation as a Sales Representative. In 2004, they joined Medline Industries as a Post Acute Sales Rep, and then advanced to Regional Vice President - HomeCare Division and Division Vice President. In 2020, they joined WellSky as an Enterprise Sales and Business Development Executive. In 2021, they founded and became CEO of Trustree Consulting LLC. Finally, in 2022, they became the Director of Post-Acute Growth for WellBeam Inc.

Josh Raimondi attended California State University, Chico from 1998 to 2002, where they earned a Bachelor of Science in Business Marketing.