Administrative Team
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Mr. Florio started his education career as a Social Studies teacher at Clearwater High School in 1997, where he coached Track, Cross Country, Football and Flag Football. He left Clearwater after three years and spent the next ten years as a Social Studies teacher at Tarpon Springs High School. Mr. Florio received both his undergraduate and graduate degrees from the University of South Florida and both he and his wife are proud Bulls Alumni.
Mr. Florio became an Administrator in 2011 and worked at Boca Ciega High School and John Hopkins Middle School. While at Boca Ceiga, Mr. Florio served ninth through 12th grade and was the Athletic Director. At Hopkins Middle School, Mr. Florio served as the Assistant Principal over the Arts Magnet Program. In 2015, Mr. Florio was named Pinellas County Music Educators Administrator of the Year. In 2017 he was named Outstanding Administrator by the Suncoast Football Coaches Association.
He was named the eleventh Principal of Hollins High School in 2015. Currently, he serves as the Principal of Clearwater High. He believes in teamwork and that when teachers, staff, parents, and students work together there is nothing they cannot accomplish. Mr. Florio has set a high bar as our mission is to be the best public high school in the state of Florida by developing leaders for careers and jobs not yet imagined.
Jennifer Chenier
Assistant Principal
Email: chenierje@pcsb.orgMs. Jennifer Chenier, grew up in Pumpkin Center, Louisana, about 40 miles from the French Quarter in New Orleans. She graduated from Ponchatoula High School, and started her secondary educational career at LSU and finished her Bachelor's Degree at Louisiana Tech in Speech Communications and Social Studies Education. She received her Masters plus 30 in Educational Leadership at Southeastern Louisana University. Prior to moving to Clearwater, FL, Ms. Chenier worked in the Louisiana Public School System serving as a teacher, assistant principal, and district facilitator over twenty-four years.
Subsequently, she transitioned into Pinellas County Schools teaching Social Studies at St. Pete High for 2 years, before taking her current position at CHS. She serves as the administrator of Athletics and Activities, and oversees our Language Arts department. She feels privileged to be a part of the Clearwater High School family and excited to support the amazing traditions of the crimson and gray. Go Tornadoes!
Cynthia Ramos-González
Assistant Principal
Email: ramos-gonzalezc@pcsb.orgMs. Cynthia Ramos-González grew up in Puerto Rico and began her journey with Pinellas County Schools in 2006. Before that, she served as an ESOL teacher in Puerto Rico for two years. 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-González 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 ESOL and Mathematics and is proud to be a Tornado!Janeen Watkins
Assistant Principal
Email: watkinsja@pcsb.orgMs. Janeen Watkins is a product of Pinellas County Schools, having graduated from Gibbs High. She graduated from Saint Petersburg College with a Bachelors in Elementary Education, with Reading & ESOL Endorsements, as well as ESE and PE certifications. She earned her Masters from St. Leo University in Educational Leadership and earned her Board Certification in Behavior Analysis from the Florida Institute of Technology.
In her previous role, she worked with various ESE Departments District-wide, supporting various programs and initiatives at all levels. She is currently serving Clearwater HS as the administrator over Discipline, Attendance, Technology, and oversees our Science and ESE departments and our CAICC and AICE Program. She loves her role at Clearwater High. Go Tornadoes!
Mason Woodside
Assistant Principal
Email: woodsidem@pcsb.orgMr. Mason Woodside grew up in Southern Illinois and graduated from Pinckneyville High School. Mr. Woodside received his Bachelor’s Degree from Southern Illinois University and his Masters Degree in Educational Leadership from St. Leo University. Following the start of his career in education as a teacher and a baseball and basketball coach, Mr. Woodside stepped into an administrative role in New Berlin, IL in which he served for 3 years as an assistant principal and principal. Prior to his current position at Clearwater High School, he served as an Assistant Principal at Palm Harbor University High School.In 2023, Mr. Woodside was named the Outstanding Athletic Administrator by the Suncoast Football Coaches Association. Additionally, he oversaw the Palm Harbor University High School Athletic program that won both Pinellas County Schools Superintendents Cups for the top overall team GPA and top overall Athletic Program during the 2023-2024 school year.He is currently serving as the Assistant Principal over Curriculum, administrator over School Safety, and Social Science. He loves being a Tornado!
