2026-2027 Administrative Promotions, New Hires, and Changes 

Leadership update as of June 8, 2026, for the 2026-2027 school year. 

Interim Chief Academic Officer

 

Dr. Jennifer Thomason will serve as the interim chief academic officer, effective immediately. 

 

Dr. Thomason began her career with Hampton City Schools in 2010 as an elementary teacher, serving students at both Tarrant Elementary School and Bryan Elementary School. In 2020, she was promoted to digital learning specialist and later advanced to coordinator of innovation and digital learning in 2023. For the past two years, she has served as the director of curriculum, instruction, and assessment, providing leadership for teaching and learning initiatives across the division.

 

She earned both her bachelor's and master's degrees from Old Dominion University, as well as an Educational Specialist degree in Educational Leadership and Policy Studies from Virginia Tech.

 

She later returned to Old Dominion University to earn her doctorate in educational leadership.

Interim Director of Curriculum, Instruction, and Assessment

 

Michele Vinnie will serve as the interim director of curriculum, instruction, and assessment, effective immediately. 

 

Vinnie brings nearly two decades of experience in Hampton City Schools. She began her career as a mathematics teacher, spending 10 years teaching at Syms Middle School, Kecoughtan High School, and Hampton High School. She later joined the Curriculum, Instruction, and Assessment team as a mathematics teacher specialist, where she served for four years before being named the school division’s mathematics curriculum leader, a role she has held for the past four years.

 

She earned a bachelor's degree in mathematics from Christopher Newport University and a master's degree in education from Regent University.

 

Interim Math Curriculum Leader

 

Ashley O’Malley will serve as the interim math curriculum leader, effective immediately. 

 

O’Malley began her career in education at Syms Middle School in 2011 as a math teacher. Her leadership roles have included but not limited to assistant principal, math coach, and most recently as a secondary math teacher specialist. 

 

She earned her bachelor’s in secondary education from Kutztown University and her master’s in administration and supervision from Old Dominion University.

 

At the June 3, 2026, meeting of the School Board, the Hampton School Board approved the following administrative promotions, effective July 1, 2026:

Principals

 

Sandra Taylor has been promoted to an elementary school principal, location to be determined.

 

Taylor has six years of service as an assistant principal in Hampton City Schools. She most recently served three years as assistant principal at Machen Elementary School and, prior to that, spent three years as assistant principal at Cooper Elementary Magnet School for Technology.

 

Before joining Hampton City Schools, Taylor began her career as a Freshman Academy and English teacher in Suffolk Public Schools. She also taught in two other school divisions before joining Hampton City Schools as a literacy support specialist at Syms Middle School, where she served for two years.

 

Taylor earned a bachelor’s in English from Washington & Jefferson College, a master’s in education from Regent University, and a post-master's certificate in educational leadership and administration from The George Washington University. 

 

Sierria Ware has been promoted to an elementary school principal, location to be determined.

 

Ware has served the past three years as an assistant principal at Phenix PreK-8. Prior to Phenix, she served as an assistant principal at Andrews PreK-8 for two years. 

She began her career in education at Hampton High School where she served in the roles of an English teacher, the Academies of Hampton Maritime Academy team lead, an English instructional leader, and a credit recovery coordinator.

 

Ware earned both her bachelor's and master's degrees from Old Dominion University and holds a postgraduate professional license in administration and supervision.

 

 

At the May 6, 2026, meeting of the School Board, the Hampton School Board approved the following administrative promotions, effective July 1, 2026:

Assistant Principals

 

Maurice Horton has been promoted to a high school academy principal, location to be determined. 

 

Horton has served as a middle school assistant principal at Syms Middle since 2023. He joined Hampton City Schools in 2019 as a special education teacher at Bethel High School. Prior to coming to Hampton, he worked with Newport News City Schools as an instructional assistant and later as a special education teacher at both the elementary and middle school levels.

 

His leadership experience includes serving as interim dean of students at Bethel High School, lead facilitator for the HCS math department collaborative learning team, an HCS induction mentor, and leader of the Boys 2 Men Mentorship program. He is committed to supporting student achievement and building a positive, collaborative school environment for both students and staff.

 

Horton earned a bachelor’s degree in recreation and leisure studies from the University of Mount Olive, a master’s degree in special education from Grand Canyon University, and a certificate in administration and leadership from the Virginia Department of Education.

Heather Woodruff has been promoted to the role of academy principal at Phoebus High School.

 

Woodruff has served as interim academy principal at Phoebus High School since November 2025. Prior to Phoebus, she was at Bethel High School as a CTE teacher since 2013. During her time at Bethel, she held several leadership roles, including Academy lead for Transportation, Analytics, Information, and Logistics; CTE instructional lead; and summer school site coordinator. She also facilitated and engaged students in the Chick-fil-A Leader Academy, a national leadership development program. She began her career with Hampton City Schools in 2002 at Jones Magnet Middle School, later serving as an instructional technology resource teacher from 2007 to 2010, and then supporting both Phenix and Andrews from 2010 to 2013. Before joining HCS, she taught high school business education in Westmoreland County Schools.

 

Woodruff holds a bachelor’s degree in business education and a master’s degree in curriculum and instruction with a focus on instructional technology, both from Virginia Tech, as well as a master’s degree in educational leadership from William & Mary.