Dr. Maestas embarked on his career in education after graduating from New Mexico Highlands University and teaching in the Longmeadow (MA) Public Schools. During that time, he also worked as Program Coordinator at Mount Holyoke College. After earning a Master’s Degree in Education from Springfield College, Dr. Maestas began his administrative career as assistant principal at North Brookfield Junior/Senior High School in North Brookfield, Massachusetts. Dr. Maestas’ tenure in the Plymouth Public Schools began after a three-year stint as principal in the Old Rochester (MA) Regional School District. Serving as Plymouth’s Coordinator of Media and Technology Services, he worked with all K-12 schools in implementing hardware, software and technology standards into the district curriculum. It was during this period Dr. Maestas served as an adjunct professor at Endicott College in Beverly, Massachusetts and Framingham State College, and as a senior visiting lecturer at Bridgewater State College. Following a brief tenure as principal of Plymouth South Middle School, Dr. Maestas was promoted to Assistant Superintendent in 2003. During that time, he received a Certificate of Advanced Graduate Study from Regent University. He later earned his Ed.D. from Regent University in 2010. Dr. Maestas became superintendent of the Plymouth Public Schools in 2008.
During his seven years at the helm, Dr. Maestas has worked extensively with school committees and local boards to develop innovative programs to benefit the youth of the community. Dr. Maestas has also been a facilitator in the construction of the new, $84 million Plymouth North High School, and $107 million Plymouth South High School project slated to open in September of 2017. Married, Dr. Maestas resides in Marion, MA with his wife Ruby and their children Martin, Gary and AJ.