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!
R.J. Denton
Assistant Principal
Email: dentonr@pcsb.orgMr. R.J. Denton grew up in St. Petersburg, FL and went to high school locally in Pinellas County, attending Keswick Christian School. Upon graduation, he attended the University of South Florida, graduating Cum Laude in 2011 with a Bachelor of Science in Secondary Social Science Education. In 2016, he completed his Masters program at the University of South Florida, graduating with a degree in Educational Leadership.Prior to joining the administrative team, Mr. Denton spent 8 years teaching various Social Studies courses at Clearwater High School, and coached Football, Cross Country, and Track & Field at the school. He was nominated for Teacher of the Year by Clearwater High School in 2016, and was the Cross Country Coach of the Year in 2016-17, after having won a Conference Championship earlier that year. He also oversaw the Freedom Ambassadors Civil Rights program, and has worked on many of the initiatives currently in place at the school. He currently serves as the administrator of Curriculum, Testing, Graduation, and our Mathematics department. He is a Tornado through and through and is proud to be a member of this amazing administrative team!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 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 administrator of Facilities, Transportation, Safety, and oversees our Support Staff, our Social Science and ESOL Departments and our AICE Program. He loves being a Tornado!
