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Sheila Jepson - Principal


Sheila started her career in 1986 as a high school Special Education teacher at Bonny Eagle.  In 1995 she worked for 2 years at the district office - one year in Curriculum and one year as the Asst Special Education Director.  She returned to BE as an assistant principal then became the principal in 1999.  She served as principal at BE until 2006. 

In the Fall 2006 Sheila became an Asst Principal at Deering HS and worked there until 2015.  She then worked at the district office in Academics for a year and a half.  Sheila became the interim principal at PHS in the Fall of 2016 and was approved as the principal in 2017.  

Sheila has a Bachelor's degree in education from UMF and a Masters in Education from Plymouth State University, Keene State College and Gallaudet University.  

Sarah Obare - Co-Assistant Principal


Sarah joined the Portland Public Schools in 2009 as a mathematics teacher at Deering High School. For the past nine years, she has served as a teacher leader at Portland High School, leading the ninth-grade team and teaching mathematics. Before joining the district, she taught at both the middle and high school levels in Baltimore and throughout Maine.

Sarah has served on many Portland Public Schools’ committees focused on equity, teacher evaluation, and the transition from middle to high school. She holds a bachelor’s degree in mathematics from the University of Maine at Farmington and a master’s of arts in teaching: secondary mathematics from Johns Hopkins University. She was recommended by PPS for the Leaders for Tomorrow’s Schools cohort at the University of Southern Maine and in 2017 earned a certificate of advanced study in educational leadership. She is passionate about creating more equitable schools by analyzing data and systems to ensure all students have access to opportunities and success.

Sarah lives in Portland with her husband and sons, who have attended Rowe, Talbot, Lincoln, and Portland High School. She is honored to have been chosen as an assistant principal by Portland High staff, students, and parents.

Caitlin LeClair - Co-Assistant Principal


Caitlin started her career in 1997 as a middle school social studies teacher in Maryland. In 2002 she moved to Maine and began working for the Portland Public Schools at King Middle School. She was a social studies teacher until 2016 when she became the principal.  In the fall of 2023, Caitlin became an Assistant Principal at Portland High School. She loves working in schools with students and teachers.

Caitlin has a bachelor’s degree in education from the University of Maine in Orono and a master’s degree in education from USM.  She lives in Portland with her husband, who also works at PHS, and daughter, a graduate of Portland schools. Outside of PHS she enjoys  spending time with family and traveling. She is honored to be an assistant principal at Portland High.

Lance Johnson - Co-Curricular/ Athletics Director


Lance has spent the last 25 years working in the Alternative Education and Math Departments at Portland High School.  He also spent 21 years as an assistant football coach at Portland High, and the last 10 years as the head football coach at Scarborough High School.

Lance holds a bachelor of science degree in Sport Management from the University of Southern New Hampshire. He has worked closely with local Athletic Administrators and leaders at the MPA as a member of the MIAAA. He was born and raised in Portland, one of 6 siblings who all graduated from Portland High School. He and his wife, Tara, have a daughter Hannah. Lance is passionate about working with high school students, and is excited to work with all students in pursuing their interests in the extended classroom of Co-Curricular activities. In his free time, he enjoys spending time with animals on his farm, fishing and family trips to York Beach.