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Caleb Stevens has a diverse work experience. Caleb started their career at Walmart in 2017 as an Overnight Dairy Associate. In 2018, Caleb worked as a Mason at JCB Masonry until April 2019. Later in 2019, they joined Collegiate Entrepreneurs as a Branch Manager and was promoted to the position of Operations Manager at Collegiate Entrepreneurs Painting Services in August 2019.

Caleb Stevens completed their education at various institutions. Caleb obtained a Bachelor of Applied Science degree in Marketing from Castleton University, where they studied from 2017 to 2020. Prior to that, they earned a diploma from Lyndon Institute in 2016. Their secondary education began at St. Johnsbury Academy, where they completed their high school diploma from 2012 to 2015.