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Rolanda Stevens began their work experience in 2010 as a Sales Transaction Assistant at Best Buy, where they worked until 2013. Rolanda then joined Teach For America as a Teacher from 2013 to 2015. During this time, they also served as a 5th Grade Teacher at Charlotte Mecklenburg Schools from 2013 to 2015. Rolanda continued their teaching career as a 6th grade teacher at School District of New Berlin from 2015 to 2016. Rolanda briefly worked as a 5th grade teacher at Milwaukee College Prep School in 2016 before leaving due to a family circumstance. In 2017, they joined Management Research Services, Inc (MRS, Inc) as a Telephone Interview Underwriter. Eventually, they transitioned to the role of Human Resources Administrative Assistant in September 2018.

Rolanda Stevens earned a Bachelor's degree in Sociology from the University of Southern Maine, where they studied from 2006 to 2010. Rolanda further pursued their education at the same university, completing a Masters in Teaching and Learning (MTL) degree in Elementary Education and Teaching from 2011 to 2017.