Complex sentence: Each year, they will dedicate the yearbook to an educator or administrator who exceeded expectations, or to someone who served at NRHS for a long time and is either retiring or leaving their position.
Split into simpler sentences: Each year, they will dedicate the yearbook to a faculty who exceeded the expectation as an educator or an administrator. Or they will dedicate the yearbook to someone who served as an educator/administrator at NRHS for a long time, and is either retiring or leaving their position.