Administration
Carlie Frederick - Assistant Principal
Carlie Frederick began her professional career in 2004 working with teens in non-profit mental health at Sweetser and Preble Street. She has served as an educator in Portland Public Schools since 2010, starting as a math teacher and moving into roles as a Chapter 104 Math Consultant, Math Coach, Teaching Strategist/Instructional Coach, and, as of August 2025, Assistant Principal at Deering High School. Carlie is passionate about making learning accessible, rigorous, meaningful, and enjoyable for all students. She is a strong advocate for restorative practices and fostering inclusive, supportive school communities. A lifelong math enthusiast and lover of the arts, Carlie enjoys making pottery, painting, and exploring creative projects. As a parent of two high school students, she deeply understands both the complexities and the joys of the high school experience — and brings that empathy to her leadership.
Caitlin Miller - Interim Assistant Principal
Caitlin Miller brings over 18 years of experience in public education, including 9 years in special education leadership. Caitlin spent the majority of her career working in Philadelphia Public Schools before moving to Maine. She is currently in her third year with Portland Public Schools and is excited to join the Deering High School community as Interim Assistant Principal, where she is committed to student-centered leadership, creating engaging learning environments for all students, and building supportive school communities.
Caitlin earned her Bachelor of Arts in Sociology and Philosophy from Villanova University, a Master’s degree in Multicultural Education from Eastern University, and post-master’s degrees in Educational Leadership from Indiana University and in Special Education Law and Policy from Drexel University. Her professional work is grounded in equity, collaboration, and advocacy for all learners.
Outside of school, Caitlin enjoys spending time outdoors with her two energetic boys, Finn (5) and Henry(3), as well as kayaking, hiking, skiing, yoga, travel, live music and art—activities that keep her grounded, active, and creatively inspired.
Melissa Labbe - AdminTeacher Leader
With over 30 years of experience in education—spanning vocational, middle, and high school levels, she has been a mainstay of the Deering High School community since 2001. Her leadership journey includes five years at the district’s central office as a District Math Leader and Summer Programs Coordinator, grounding her work in both classroom instruction and administrative strategy. Melissa earned her Bachelor of Arts in Mathematics and Computer Science from the University of Maine at Farmington and her Master of Science in Education in Curriculum, Instruction, and Assessment from the University of New England. Currently pursuing her ESOL certification, she is focused on creating inclusive learning environments where both staff and students are supported in exploring their passions and discovering their true purpose.