Dr. Gregory J. Pilewski began his career in 1998 as a classroom social studies teacher working in schools in Maryland (Harford County Public Schools and Baltimore County Public Schools), Ohio (Shaker Heights City Schools), and in London, England (Westminster Educational Authority). Dr. Pilewski was the Harford County Public Schools First Year Teacher of the Year recipient being selected among 800 new teachers also in 1998. While with the Baltimore County Public Schools (BCPS) from 2000 to 2006, Dr. Pilewski worked as social studies teacher then as a professional development trainer in the area of new teacher mentoring and support of teachers in challenging secondary schools and two alternative high schools. He finished his work with BCPS as the district Coordinator of Smaller Learning Communities (SLC) and College Board Programs supporting the expansion of specialized career academies and developing partnerships with local businesses and higher education institutions while increasing Advanced Placement (AP) courses.

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In 2006, he moved to the Anne Arundel County Public Schools (Maryland) where he held the positions of Director of Curriculum, supervising 20 district curriculum coordinators, and then as the Director of Humanities expanding instructional program and offerings for students Prek-12. In 2012, Dr. Pilewski was elevated to the position of Executive Director of Curriculum Innovation and Design providing leadership and direction for the district’s first innovative Curriculum Management Plan; developing and implementing a system-wide vision for curricula, instructional strategies and assessment models; and managing and evaluating the school district’s digital e-curriculum management improvement model. In 2013, Dr. Pilewski was promoted to the Assistant Superintendent for Curriculum and Instruction where he provided leadership, planning and alignment to the transition of the Maryland College and Career Readiness Standards for 79,500 students, 6,500 teachers, and 129 schools while supervising three executive directors in the areas of Teaching and Learning, Curriculum Innovation and Design, and Special Education.

Dr. Pilewski has also worked as a consultant in the areas of Science, Technology, Engineering, Arts, and Mathematics (STEAM) integration, Common Core State Standards, National Core Arts Standards, transformational leadership, and designing district curriculum management plans. He has worked with school systems and state departments of education in New Jersey, North Carolina and Virginia.

In 2015, Dr. Pilewski became the Queen Anne's County Public Schools' (Maryland) Assistant Superintendent for Instructional Services and School Improvement. Shortly upon his arrival, Dr. Pilewski was credited with narrowing the instructional focus for the school system into five strategic areas to improve student learning to include: (1) Organizational Effectiveness, (2) Early Learning and School Readiness, (3) Curriculum, Instructional Tools, and Assessment, (4) Leadership and Professional Learning, and (5) Monitoring Progress and Performance. Each focus area was organized from the 2016 Curriculum Management Audit in an effort to close gaps in student achievement. Further, Dr. Pilewski was credited with accelerating the school systems work on equity and diversity with an emphasis on building strong relationships with key stakeholders.

Dr. Pilewski was then appointed to Interim Superintendent of the Queen Anne’s County Public Schools on July 1, 2016. Under his leadership during the 2016-2017 School Year the school district showed significant improvement in student performance data. In fact, in 2016-2017 Queen Anne’s County Public School led the state in the percentage of students “Meeting or Exceeding Expectations” in English Language Arts (ELA) in grades 6, 7 and 8. At the high school level, students improved by more than 20 percentage points with 66.5% of English 10 test takers having met or exceeded expectations. At the time, this was the second highest rate in the state of Maryland. In math, students scored in the top quarter of the state in all grades. The percent of students meeting or exceeding expectations increased in 2016-2017 in all grades with the exception of grades 6 and 8.

On July 1, 2017, Dr. Pilewski returned to his role as Assistant Superintendent under the leadership of Dr. Andrea M. Kane, who was appointed Superintendent of the Queen Anne’s County Public Schools on July 1, 2017. Due to his leadership capacity, Dr. Kane reassigned Dr. Pilewski to the position of Deputy Superintendent on July 1, 2018 directly supervising the departments of School Administration, Curriculum and Instruction, Student Service, Accountability and Testing, Special Education, Teacher/Principal Mentoring, and Technology with direct supervision of 14 curriculum supervisors and 14 school principals. In addition, Dr. Pilewski is credited with improving academic programs and achievement of all students through expanded educational opportunities including aligning curriculum, instruction, and assessments, streamlining academic interventions Prek-12, expanding Advanced Placement (AP), Dual Enrollment, Dual Credit, and Early College Academy programs, visual and performing arts, world languages, and virtual learning opportunities through a lens of equity.

Since March 12, 2020, Dr. Pilewski is credited with designing and implementing the QACPS comprehensive district Continuity of Learning Plan in response to COVID-19 and the school systems Roadmap to Reopen Plan ensuring every student (Prek-12) engages in high quality instruction regardless of the delivery model. Further, Dr. Pilewski provided the vision and leadership to implement a unique project management structure through the use of Targeted, Immediate, Group Execution, and Response (TIGER) teams to ensure the district plan included the following state required areas: (a) recovery plan is available on district website, (b) equity plan, (c) recovery plan stakeholder group, (e) identification of gaps in learning, (f) Maryland College and Career Ready Standards, (g) IDEA, Section 504, and ADA, (h) procedures for individuals who test positive for COVID-19, (i) safety protocols for cleaning of facilities, (j) procedures for safe transportation of students, (k) procedures for tracking attendance, (l) communication plan, and (m) a roadmap for interscholastic athletics and activities.

Dr. Pilewski earned a bachelor’s degree in secondary education in the area of social studies from Clarion University of Pennsylvania in 1997. He earned a master’s degree in curriculum, instruction, and administration from McDaniel College in 2006 and a doctoral degree in education from Northcentral University with an emphasis in organizational leadership in 2020. Dr. Pilewski’s dissertation topic and research interest includes: A Case Study of Principals’, Curriculum Supervisors’, and District Executive Leaders’ Perceptions Regarding Implementing District Improvement Initiatives.

Dr. Pilewski and his beautiful wife, Bianca, will reside in the North Little Rock School District with their two Labrador retrievers, Willow and Scupper and their two nearby horses, Luna and Denny.