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Shay Lea Strain has a solid background in the education sector, with experience in various roles and school districts. Shay Lea began their career in 2006 as a Vice Principal at Boerne ISD, where they worked until 2013. Shay Lea then joined Comal Independent School District as an Administrator, where they remained until 2019. In 2017, they took on a position at Texas Connections Academy in the field of Education, before transitioning to their current role at Boerne ISD in 2019.

Shay Lea Strain has a diverse education history. Shay Lea attended Edna High School, where they completed their secondary education, but no specific degree or field of study information is available. Shay Lea then pursued their Bachelor of Science degree in Health Information/Medical Records Administration/Administrator at Texas State University. Later, they earned their first Master of Education degree from the University of Houston, specializing in Educational, Instructional, and Curriculum Supervision. Shay Lea Strain continued their educational journey by completing a second Master of Education degree at the University of Houston-Victoria, focusing on Curriculum and Instruction with Principal Certification.