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Kelley Masters has a diverse range of work experience in the education field. Kelley started their career as a Year-long Elementary Teaching Intern at International School Manila in 2011. Kelley then worked as an Associate Teacher in Kindergarten at The Nueva School from 2012 to 2013. Kelley continued their role at The Nueva School as an Associate Teacher in 1st Grade from 2013 to 2014. Kelley also served as a Lead Counselor at The Nueva School and Nueva Summer Camp during the summers of 2013 and 2014. Kelley gained further experience as a Student Teacher in 4th/5th Grade at Henry J Kaiser Elementary School in 2014. Kelley then took on the role of a Student Teacher in 1st Grade at Berkeley Arts Magnet Elementary School from January to June 2015. Following this, Kelley worked as a 1st Grade Lead teacher at The New School of San Francisco. Currently, they hold the position of a Second Grade Head Teacher at Town School for Boys since July 2019.

Kelley Masters earned their Bachelor of Arts (B.A.) degree in American Studies and Educational Studies from Carleton College in 2011. Kelley went on to complete their Master's Degree in CA Multiple Subject Credential and Masters in Education at Mills College from 2014 to 2017.