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Bailey Sherlin began their work experience in 2006 as an Instructional Assistant at Bullis Charter School. From 2007 to 2012, they served as a Lead Teacher at Aspire Public Schools. In 2012, they worked as an Instructor at Mad Science Group. In 2013, Bailey held various roles including Graduate Student Fellow at Education Pioneers, STEM Analysis and Advocacy Fellow at Education Trust West, and Systems Advocacy/Planning Intern at Treehouse. From 2014 to 2020, they worked at Achievement Network (ANet) as Manager, Network Support and Analysis and later as Director, Support & Operations. Since 2020, Bailey has been employed by KIPP Texas Public Schools, initially as the Regional Manager of School Operations and currently as the Senior Director, Operations Strategy.

Bailey Sherlin holds a Master of Public Administration (MPA) degree in Non-Profit/Public/Organizational Management from the Evans School of Public Policy & Governance, University of Washington, which was obtained between 2012 and 2014. Earlier, Bailey earned a Master of Science (MS) degree in Education-Curriculum from California State University - East Bay in 2009. Bailey also holds a Multiple Subject Credential from Cal State Monterrey Bay, acquired in 2007. The education journey began at Stanford University, where Bailey completed a Bachelor of Arts (B.A.) degree in English Language and Literature/Letters in 2006.