Principal Taylor Henderson

Principal Henderson is proud to be the seventh principal of Countryside High School and is a product of Pinellas County Schools, graduating from Dixie M. Hollins High School in 1996.  He is in his seventh year as principal at Countryside High School, and has 21 years of large high school administrative experience in Pinellas County Schools.

Prior to entering administration, Principal Henderson taught English and coached cross-country and soccer at Boca Ciega High School and Dixie M. Hollins High School.  He received both his Bachelor of Arts in English Education ('00) and Master's Degree in Educational Leadership ('05) from the University of South Florida. 

Assuming the role of principal of the historic Countryside High School in 2020, Principal Henderson embraces the great traditions of the garnet and gold.  He strives to be visible at all times at school, listening to all stakeholders, and supporting all the Cougars.  He strives to be a "student-first" principal and focuses on building strong and enduring relationships to support a positive school climate.  

During his administration, Countryside High School has consistently increased teacher and staff retention rates, student academic performance and acceleration, and achieved national recognition through the Magnet Schools of America.  Principal Henderson has been recognized as an "Administrative Hero" by the Pinellas County Parent Teacher Organization, and an Administrator of the Year by the Pinellas County Art Teacher Association. 

Principal Henderson is a proud father of two sons, Taylor Jr. and Aaron, three grandchildren, Seraphima, Ezra, and Nectaria Jane, and is married to the former Jennifer Gil.  

Assistant Principal Robert Murphy

Students Last Name K-T

murphyrobe@pcsb.org; ext. 2017

Robert Murphy is a proud product of Pinellas County Schools, having graduated from Dunedin High School in 2009. He received a degree in secondary math education from St. Petersburg College in 2014 and a master's degree in educational leadership from Florida State University in 2022. 

Mr. Murphy started with Pinellas County Schools in college as a plant operator at Safety Harbor Middle School. Mr. Murphy began teaching in 2014 and taught mathematics at Dunedin High for 10 years. Mr. Murphy is excited to be part of Countryside High School! Go Cougars!

Assistant Principal Erin Overall

Athletic Director

Students Last Name A-J

overalle@pcsb.org; ext. 2016

Mrs. Erin Overall is both our Assistant Principal and Athletic Director here at Countryside High School. She has a Bachelor of Science in Mathematics from Lambuth University in Jackson, Tennessee, where she captained the Women’s Soccer Team for four years. She also has a Master of Arts in Teaching from Grand Canyon University, and a Graduate Certificate in Educational Leadership from the University of North Florida. 

Mrs. Overall taught mathematics at her alma mater Mosley High School in Panama City, Florida, for 14 years before becoming an administrator there. She has been an Assistant Principal at both the middle and high school level, where her primary responsibilities ranged from curriculum, assessment, professional learning communities, and athletics. Her heart for education and creating a student-centered environment for learning is what drives her to help grow students at Countryside into successful citizens of Pinellas County! 

Assistant Principal Cynthia Ramos-Gonzalez

iSTEM Coordinator and Assistant Principal for Curriculum

Ms. Cynthia Ramos-Gonzalez grew up in Puerto Rico and began her journey with Pinellas County Schools in 2006. She earned her Bachelor of Science in Teaching English as a Second Language (K–12) from the Inter American University of Puerto Rico.

In 2015, Ms. Ramos-Gonzalez completed her master's degree in educational leadership from Saint Leo University, where she is currently pursuing a Doctorate in Educational Leadership.

Throughout her career in Pinellas County Schools, she has held multiple instructional and leadership roles, including ESOL, Reading, Gifted, and World Languages teacher, Reading Coach, Assistant Principal, and World Languages Specialist. She currently oversees curriculum and is proud to be a Countryside Cougar!