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Caito Stewart has a diverse work experience. They started their career in 2006 as an artwork installation assistant at the St. Louis Art Museum. They then worked as a sales associate at Artmart, where they gained knowledge about various art supplies and assisted customers. Caito also worked as a sales associate at A.I. Friedman, providing customer service and sales support.

In 2008, Caito joined ECC Foreign Language Institute as a Native English Instructor, teaching English to adults and children. They later became a Kids' English World Trainer, responsible for developing and conducting training programs for children's English lessons. Caito also worked as a Shinjuku/Yokohama Area Trainer, overseeing teacher training and lesson quality control.

Caito had an internship at Immaculate Conception, Inc Janine Antoni's Studio, where they assisted the artist in creating ceramic sculptures and gained knowledge about the financial and organizational aspects of running an artist studio.

In 2018, Caito established their own art business, Caito Stewart Fine Art. They taught studio art classes and summer camps to children at One River School of Art + Design, where they eventually held positions as Art Instructor, Assistant Director of Education, and Director of Education.

They also had a brief experience as an Assistant Operations Manager at Ichiran and facilitated an art healing grief workshop.

Caito completed their graduate studies at Pratt Institute, where they worked as a Graduate Teaching Assistant and Graduate Assistant, managing the Sculpture Shop.

Overall, Caito has a strong background in art education, teaching, and administrative support.

Caito Stewart attained a Master of Fine Arts degree in Sculpture from Pratt Institute, starting in 2018 and completing the program in 2020. Prior to that, Caito pursued a Bachelor of Fine Arts degree in Painting at Washington University in St. Louis from 2003 to 2007.