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Andrew Tosiello has over 25 years of work experience. In 1996, they began their career as a Gallery Assistant at Boston University Art Gallery. Andrew then worked as an Exhibitions Installer at Harvard University Art Museums from 2002 to 2005. From 2005 to 2012, they were a Local Booking Coordinator, Dispatch, and Art Installer at Ship/Art International. Andrew then worked as a Merchant and Crew Member at Trader Joe's from 2012 to 2014. From 2014 to 2019, they worked at Udemy as a Product Manager, Email Marketing Manager, and Customer Support Associate. Andrew most recently worked as an Email Developer at Varo Money Inc. from 2019 to 2021. Currently, they are a Marketing Operations at ClassDojo.

Andrew Tosiello attended Belmont Hill School from 1992 to 1996. Andrew then went on to Boston University College of Fine Arts, where they earned a Bachelor of Fine Arts (BFA) in Painting in 2000. In 2006, they completed a Master of Fine Arts (MFA) in Painting at California College of the Arts.