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Raymond Gillespie has a diverse range of work experience. Raymond started working at Juice Bar of the Future, LLC in 2019 as a Marketing Consultant and worked there until March 2023. In 2019, they also became a Marketing Director at Elevator Studio, where they still hold the position. From February 2020, Raymond joined 100MillionAcademy as a Social Media Director and is currently employed there. In May 2021, they joined ClickUp as a Social Media Coordinator and later transitioned to a Partnerships Coordinator role. Since March 2023, Raymond has been serving as the Director of Operations at The Money Mondays.

Raymond Gillespie attended Landmark in 2012, where they studied Ontology. It is unclear when their education at Landmark concluded, as no end year is provided. Additionally, Raymond achieved an Associate's degree in Business, Management, Marketing, and Related Support Services from the University of Pittsburgh. The exact dates of their enrollment at the University of Pittsburgh are unknown.