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Henry Cleaves has extensive work experience in various roles and industries. Their most recent position was as an Account Executive at Mango Languages, where they began in March 2023. Prior to that, they worked at Wayside Publishing as an Account Manager from September 2021 to March 2023, and also held the position of Bilingual Digital Support from February 2021 to August 2021. In 2020, Henry worked as a Regional Field Director at CADC from September to December. From October 2019 to September 2020, they worked as an Outside Sales Representative at HelloFresh. In June to August 2019, they worked as an Executive Assistant at GVB Biopharma.

Henry Cleaves attended Waynflete School for high school, but it is unknown when they started and ended their education there. From 2015 to 2019, they attended Lewis & Clark College, where they obtained a Bachelor of Arts degree in Spanish Language and Literature, as well as Rhetoric & Media Studies. In 2017, they briefly studied Architecture at the Universidad de las Artes de Cuba, and in 2018, they studied Film/Cinema/Video Studies at Pontificia Universidad Católica de Chile.