Thomas Milaschewski
Beverly,MA
Summary
Experienced and collaborative educational leader with a proven record of impact across K–12 systems. Currently serve as Superintendent of Schools in a high-performing Massachusetts district, overseeing all instructional, operational, and community-facing initiatives for over 4,000 students and 1,000 staff, and a $60M+ annual budget. Recognized for exemplary performance across all Massachusetts standards for superintendents—Instructional Leadership, Operational Leadership, Family/Community Engagement, and Professional Culture.
Overview
16
16
years of professional experience
Work History
District Reviewer
MA Department of Elementary and Secondary Education
- Served on formal school district reviews to assess and provide recommendations across six key areas: Leadership & Governance, Curriculum & Instruction, Assessment, Human Resources, Student Support, and Asset Management. Reviewed multiple districts across the state, with findings and recommendations publicly released.
Consultant
Clark County School District
- Company Overview: Las Vegas, NV – 320,000 students
- Led district-wide engagement and systems analysis to develop actionable recommendations on increasing school autonomy and coherence across 336 schools.
Consultant
Ferguson-Florissant School District
- Company Overview: MO – 11,000 students
- Supported design and development of a new, equity-centered high school, focusing on inclusive programming, academic rigor, and innovation.
Content Expert
Springpoint Schools
- Provide strategic feedback and design consultation to districts and nonprofits across the country on developing innovative high school models.
Facilitator
Public Education Leadership Project (PELP), Harvard University
- Supported improvement planning for 12 major districts including NYC DOE, LA Unified, and Chicago Public Schools. Coached the senior leadership team from Salem-Keizer (OR – 41,000 students) on systems to improve principal effectiveness.
Doctoral Residency Supervisor
Harvard Graduate School of Education
- Supervised and mentored full-time doctoral candidates, supporting those aspiring to system-level leadership roles (e.g., Superintendents, Chiefs of Schools).
Harvard PZ Facilitator
- Company Overview: Facilitated at the National Institute for Urban School Leaders and Race, Equity, and Leadership in Schools program, working with over 260 superintendents, principals, and teacher leaders nationwide.
Coaching Facilitator
PELP Summer Series 2020
01.2020
- Provided structured coaching to leadership teams from 15 school districts nationwide to design coherent COVID-19 reopening plans aligned to mission and instructional core.
Superintendent
Reading Public Schools
07.2021 - Current
- Instructional Leadership
- Led 8 of 9 schools to achieve the highest state accountability percentile rankings in district history. The only school that did not reach this benchmark was named one of only four middle schools across MA in 2024 as a “School of Recognition” for high growth and achievement.
- Redesigned district-wide literacy approach at the elementary level, resulting in district record highs in elementary literacy growth—4th in the state out of 306 districts in 2023—and highest proficiency/advanced rates in district history in 2024.
- Directed comprehensive math improvement strategies across K–8 (curriculum, assessment, professional development), leading to district record levels in achievement in 2023–2024.
- Secured DESE approval and over $500K in combined state and local funding to launch five Innovation Pathway programs in Computer Science, Engineering, Digital Media, Clean Energy, and Healthcare/Social Assistance. RMHS was selected as the state announcement site and described by the MA Secretary of Education as a “model and leader in innovation career pathways.”
- Expanded college and career readiness programs by launching the district’s first dual enrollment offerings with UMass Lowell, Endicott, and Middlesex CC and creating a new senior internship program that placed over 70% of seniors in quarter-long, real-world internships.
- Built district’s participation in the State Seal of Biliteracy, enabling over 50 students to graduate with this prestigious designation recognizing high functional and academic proficiency in multiple languages
- Operational Leadership
- Reformed district budgeting practices, unlocking funding for 35 new full-time positions over four years without additional state/town funding—including instructional coaches, assistant principals, special educators, and mental health supports.
- Secured $44M in state funding through the Massachusetts School Building Authority (MSBA) and $85M in town funding for a new elementary school. Led the district and community through the multi-year process—from grant approval to feasibility and schematic design.
- Designed and executed multi-year transition to universal, tuition-free full-day kindergarten; prior to this shift, Reading was one of only 24 communities still charging tuition, and had the highest rates in the state.
- Negotiated agreements with all five bargaining units (teachers, paraprofessionals, custodians, secretaries, food service) before contract expiration, resulting in more competitive compensation with peer districts while remaining within existing budget constraints
- Led district to a 70% increase in METCO student enrollment (the largest 1-year increase in program history) with state and local approval. The METCO CEO publicly named Reading as a “leader and model” among METCO districts.
- Partnered with Food Services to improve meal quality, leading to a 41% increase in annual meals served (111K+) compared to pre-pandemic levels. The program was selected as the host site for the statewide “More Than a Meal” tour, showcasing the impact of universal free meals.
- Launched Reading’s first Children’s Cabinet, a cross-sector initiative with town management, police, clergy, and the YMCA to better align and expand services for youth. Initiatives included youth listening sessions with 167 RMHS students (15% of enrollment) focused on belonging and inclusion, and the creation of a Community Family Closet providing free monthly access to clothing and shoes for families.
- Supported implementation of the district’s first-ever Unified Sports programming, introducing basketball, strength/conditioning, and bocce teams. Secured funding through district and community partnerships, resulting in robust interscholastic opportunities for 100+ participants.
- National Leadership, Facilitation, and Coaching
Superintendent Resident (during doctoral residency)
Medford Public Schools
06.2020 - 06.2021
- Co-led district initiatives with the Superintendent during the height of COVID-19, coordinating strategy across academics, health, operations, and family engagement.
- Designed and launched a new leadership development strategy for all 19 principals and assistant principals using coaching cycles and Communities of Practice.
- Chaired the District Reopening Steering Committee with 100+ stakeholders, including the Mayor, School Committee, union leaders, staff and families, to collaboratively develop the 2020 reopening plan.
- Represented the central office on collective bargaining teams, negotiating MOAs for all 11 bargaining units regarding reopening conditions.
Principal, Bates Elementary School
Salem Public Schools
06.2014 - 06.2018
- Led a racially, linguistically, and economically diverse Title I school of 400 students, achieving the highest CPI and MCAS proficiency scores in school history in both ELA and Math.
- Selected to serve as Mentor Principal for colleagues in Salem, supporting principals across all 4 MA leadership standards; rated “Exemplary” on evaluations and significantly above district average in all 8 categories of the Panorama Teacher Survey.
- Named candidate for Massachusetts Elementary Principal of the Year by the MSAA in 2018.
Principal Intern (during Master's studies)
Boston Public Schools
07.2013 - 05.2014
- Supported historic turnaround at the first high school in Massachusetts to exit Level 4/Turnaround status, collaborating closely with the headmaster on all school-wide instructional and operational initiatives.
Teacher
Boston Public Schools, North Shore Technical HS
09.2009 - 06.2013
- Taught special education, ESL, and math in both middle and high school settings. At Frederick, 100% of students passed benchmark math exams, achieving an average of 1.75 years of reading growth annually. At NSTHS, earned the district’s only “Exemplary” rating across all categories.
Education
Doctorate in Educational Leadership -
Harvard Graduate School of Education, Joint Program with Harvard Kennedy School and Harvard Business School
Cambridge, MA01.2021
Master's in School Leadership - undefined
Harvard Graduate School of Education
Cambridge, MA01.2014
Master's in Teaching and Curriculum - Concentration in Special Education
Boston University
Boston, MA01.2011
Bachelor of Arts - Spanish and International Studies
Colby College
Waterville, ME01.2009
Timeline
Superintendent
Reading Public Schools
07.2021 - Current
Superintendent Resident (during doctoral residency)
Medford Public Schools
06.2020 - 06.2021
Coaching Facilitator
PELP Summer Series 2020
01.2020
Principal, Bates Elementary School
Salem Public Schools
06.2014 - 06.2018
Principal Intern (during Master's studies)
Boston Public Schools
07.2013 - 05.2014
Teacher
Boston Public Schools, North Shore Technical HS
09.2009 - 06.2013
District Reviewer
MA Department of Elementary and Secondary Education
Consultant
Clark County School District
Consultant
Ferguson-Florissant School District
Content Expert
Springpoint Schools
Facilitator
Public Education Leadership Project (PELP), Harvard University
Doctoral Residency Supervisor
Harvard Graduate School of Education
Harvard PZ Facilitator
Master's in School Leadership - undefined
Harvard Graduate School of Education
Master's in Teaching and Curriculum - Concentration in Special Education
Boston University
Bachelor of Arts - Spanish and International Studies
Colby College
Doctorate in Educational Leadership -
Harvard Graduate School of Education, Joint Program with Harvard Kennedy School and Harvard Business School
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