10 Boston School Principals Worth Following in 2026

Jonno White
Aug 4
10 min read

Last updated: August 2026

This directory introduces ten current school leaders whose schools sit inside the City of Boston. It spans a district exam school, several charter schools, an arts academy and a Catholic work-study high school, making it a useful starting point for anyone exploring Boston school leadership.

As of August 2026, Boston's school landscape is unusually varied for one city. It holds the oldest public school in the United States, a growing cluster of charter schools built around single missions like music or sustainability, and Catholic schools built around work-study models found in only a few American cities. The ten people below lead schools across that whole range, from a nearly four century old exam school to a charter school that opened within the last fifteen years.

The names are presented alphabetically by surname for easy navigation, not in any order of importance. Some lead a school founded before the American Revolution. Others lead a school that opened much more recently. Each brings a different path into school leadership, from long service within one community to experience across several parts of Boston education.

This is not a ranking or a claim that these are the only Boston school leaders worth knowing. It is a practical starting point for readers interested in district exam schools, mission-built charter schools, arts education and Catholic work-study schools.

Why Boston school leadership matters right now

Boston school leadership matters right now because the city's schools face real pressure on staffing, funding and public trust at the same time as a wave of relatively new leaders have taken over long standing institutions, so knowing exactly who is in charge of which school is genuinely useful.

Several of the schools on this list changed leaders within the last two years. A new head of school at a 390 year old exam school inherits both a strong tradition and real expectations to keep improving it. A new executive director at a charter school inherits a specific mission, whether that is music education, sustainability or a Catholic work-study model, and has to keep that mission intact while running daily operations.

Boston is also unusual in how many different school types operate inside one city boundary. A reader trying to understand Boston education needs to know the difference between a citywide exam school, a neighbourhood charter school and a Catholic work-study high school, because the leadership challenges in each are genuinely different.

Knowing who leads a specific school, and what they have done, is more useful than a general sense that Boston has good schools. The ten profiles below offer a specific starting point.

1. Jason Gallagher

Head of School, Boston Latin School

Jason Gallagher is the 29th Head of School of Boston Latin School, the oldest public school in the United States, founded in 1635. He moved into the role in July 2022 after leading the Harvard-Kent K-6 School in Charlestown for 11 years, moving from a neighbourhood K-6 school to the city's historic exam school within the same district.

He is himself a Boston Latin School graduate, which gives his leadership of the school a personal dimension beyond the job title. For anyone exploring how a historic exam school is led, his move from a smaller neighbourhood school to the city's oldest institution is the relevant fact.

2. Matt Holzer

Head of School, Boston Green Academy

Matt Holzer has been Head of School of Boston Green Academy in Brighton since 2014, after joining as a founding staff member when the school opened in 2011. That gives him more than a decade of continuous leadership at one Boston school built specifically around sustainability education.

Under his leadership, the school has won the National Green Ribbon School award from the US Department of Education, which recognises whole school sustainable practices. For a reader interested in how environmental education actually operates inside a public school, that sustained, single school tenure is the useful detail.

3. Derrick Ciesla

Head of School, Codman Academy Charter Public School

Derrick Ciesla became the third head of school in the 23 year history of Codman Academy Charter Public School in Dorchester in 2024, after previously leading Russell Elementary School, also in Dorchester. He holds a doctorate in educational leadership from Boston College and spent 24 years across teaching, administration and mentorship roles before taking the position.

He moved into a school built around a strong academic standard for students from under resourced backgrounds. For a reader comparing leadership paths into Boston's charter sector, his move directly from one Dorchester public school to a nearby charter school is a distinctive route.

4. Edverette Brewster

Executive Director, Neighborhood House Charter School

Edverette Brewster leads Neighborhood House Charter School in Dorchester, one of the first charter schools founded in Massachusetts, established in 1995. He was chosen unanimously by the school's board from a pool of more than 70 applicants for the role, starting in July 2024.

Before this role he served as principal of the Holmes Innovation School in Dorchester and as a leadership coach with the Lynch Leadership Academy. For a reader tracking how Boston's oldest charter schools bring in new leadership, that unanimous selection from a large applicant pool is a useful signal of how the search was run.

5. Nicole Mack

Executive Director, Conservatory Lab Charter School

Nicole Mack leads Conservatory Lab Charter School in Roxbury, a Pre-K through 8 school built around music education. Before this role, she served as Boston Public Schools' district-wide Director of Literacy and Curriculum Design, alongside earlier work as a district-level Inclusion Specialist.

That combination of literacy and curriculum specialism now leads a school where music is the organising idea rather than an elective. For a reader interested in how a district-trained curriculum leader applies that background inside a mission-specific charter school, her career path is the relevant detail.

6. Jenna Ogundipe

Executive Director, Boston Collegiate Charter School

Jenna Ogundipe has spent her entire career at Boston Collegiate Charter School in Dorchester, joining as a history teacher in 2002 and rising through History Department Co-Chair, Dean of Administration, High School Principal and Chief Academic Officer before becoming Executive Director.

That single school, more than two decade career path is unusual even inside the charter sector, where leadership often moves between schools or networks. For a reader wanting to understand how internal leadership pipelines work inside one Boston charter school, her path is the clearest example on this list.

7. Thomas Ryan

Principal, Cristo Rey Boston High School

Thomas Ryan has led Cristo Rey Boston High School in Dorchester since 2019, after 19 years at Catholic Memorial School, most recently as Head of Middle School and Vice Principal for Mission and Integration. He holds a doctorate in interdisciplinary leadership from Creighton University and has spent his entire 24 year career in Catholic education.

Cristo Rey Boston belongs to a small national network of Catholic high schools built around a work-study model that helps fund tuition. For a reader comparing leadership models across sectors, his move from a Catholic prep school into a work-study school is a distinctive contrast.

8. Tyrone Sutton

Head of School, Boston Arts Academy

Tyrone Sutton has been Head of School at Boston Arts Academy since 2022, after working at the school in various teaching and leadership roles since 2008. He founded the school's award-winning Spirituals Ensemble, which won the 2015 WGBH Sing That Thing choir competition and helped earn the school a GRAMMY Signature School award.

That founder-to-head-of-school path, built entirely inside one arts focused exam school, gives him a level of institutional knowledge that an external hire would not have. For a reader interested in Boston's arts education pipeline, that direct link between his own programme and the school's national recognition is the relevant fact.

9. Zach Meisner

Principal, KIPP Academy Boston K-8

Zach Meisner is Principal of KIPP Academy Boston K-8 and joined KIPP Massachusetts in 2014 as a seventh grade reading teacher. He worked in the same hallway as the founding kindergarten class during the school's opening year, giving him a long view of the community's growth.

He later moved into school leadership and now leads the K-8 school. For a reader interested in continuity inside a relatively young charter school, his connection to the community from its opening year is the distinctive detail.

10. Richard Chang

Head of School, Josiah Quincy Upper School

Richard Chang leads Josiah Quincy Upper School in Chinatown, one of only a small number of International Baccalaureate-designated public high schools in Boston. Under his leadership, the school won the district's 2025 Green Building of the Year award and the associated People's Choice Award for its facility.

That combination of an academically distinctive IB programme and a nationally recognised building gives the school two separate, clear points of distinction. For a reader comparing citywide public high schools, that dual recognition in a single year is a useful marker.

What these leaders show us about Boston school leadership

Read together, these ten careers point to a few clear patterns about how Boston schools are actually led. Several leaders moved into their current role from another leadership position inside the same district or the same neighbourhood, rather than arriving from outside the city entirely. Jason Gallagher moved from one Boston Public Schools building to another. Derrick Ciesla did the same, moving from Russell Elementary School directly into Codman Academy nearby in Dorchester.

A second pattern is how often a school's specific mission, whether that is sustainability, music, the arts or a Catholic work-study model, shapes what leadership actually looks like day to day. A head of school at a mission-specific charter school is not doing the same job as a head of school at a large, long-established exam school, even though both titles sound similar on paper.

A third pattern is longevity within one institution. Several of these leaders spent years, sometimes decades, working inside the same school or the same district before taking the top role. Jenna Ogundipe's two decade climb through every leadership rung at Boston Collegiate is the clearest example, but Zach Meisner's path from founding teacher to Principal at KIPP Academy Boston follows the same shape on a shorter timeline.

The practical implication for a reader is that Boston school leadership is not one job description. A district exam school, a mission-specific charter school and a Catholic work-study high school each need a genuinely different kind of leader, and the strongest match usually comes from understanding that specific school's mission first, rather than assuming one leadership style transfers cleanly across every school type in the city.

How to use this list

Start by identifying which type of Boston school actually matters for your purpose, whether that is a district exam school, a neighbourhood charter school, an arts-focused school or a Catholic work-study school. The leadership challenges and priorities differ meaningfully between these categories, so a generic approach will miss what actually matters at a specific school.

Once you have identified the relevant school, use the role and organisation listed next to each name as your starting point. The school's website is a useful place to learn about current programmes, community priorities and contact details before reaching out directly.

If you are a Boston principal yourself, working through how your own leadership team functions is often the more useful next step than looking at other schools. A practical framework like Working Genius can help a school leadership team see where work is stalling, where energy is being drained, and where the principal is carrying too much alone rather than sharing it.

Finally, remember that leadership roles change. Several people on this list moved into their current role within the last few years, reflecting the steady movement that shapes school leadership across the city.

Frequently Asked Questions

What is the oldest public school in Boston?

Boston Latin School is the oldest public school in the United States, founded in 1635. It is currently led by Jason Gallagher, its 29th Head of School, who moved into the role in 2022 after 11 years leading the Harvard-Kent K-6 School in Charlestown.

Are Boston charter schools different from Boston Public Schools?

Yes. Charter schools like Codman Academy, Neighborhood House Charter School, Boston Collegiate Charter School and Conservatory Lab Charter School are independently operated public schools with their own boards, while schools like Boston Latin School and Josiah Quincy Upper School are run directly by Boston Public Schools.

How many schools does Boston Public Schools operate?

Boston Public Schools operates over 100 schools across the city, ranging from elementary schools to exam schools like Boston Latin School and specialised schools like Boston Arts Academy and Boston Green Academy. Each school has its own principal or head of school.

What is a Cristo Rey school?

A Cristo Rey school is part of a national network of Catholic high schools built around a work-study model, where students work one day a week in a corporate job to help fund their tuition. Cristo Rey Boston High School in Dorchester is led by Principal Thomas Ryan.

Do all Boston school leaders use the title Principal?

No. Titles vary by school type and sector. Boston Public Schools generally uses Principal or Head of School, some exam schools use Headmaster or Head of School, and several single-school charter organisations use Executive Director for the person who leads that one school.

Conclusion

Boston's school leadership landscape is more varied than a single word like "principal" suggests. The ten people on this list currently lead a nearly four century old exam school, a growing cluster of mission-specific charter schools, and a Catholic school built around a distinctive work-study model, each requiring a genuinely different kind of leadership on a daily basis.

Together, these ten leaders offer a useful view of Boston education across school types and neighbourhoods. Their careers show how teaching, curriculum work, programme leadership and long service within one community can all lead to the top role in a school.

If you are exploring Boston school leadership, start with the school type that matters for your purpose. Then use the people and organisations here to understand how leadership looks different across exam schools, charter schools, arts education and Catholic education.

Bring a practical leadership conversation to your Boston school

Jonno White helps school leadership teams build the kind of trust and communication that makes everything else easier. For a practical keynote, workshop or facilitated leadership session for your Boston school or district, email jonno@consultclarity.org.

About the Author

Jonno White is a Brisbane-based leadership consultant, keynote speaker and Certified Working Genius Facilitator, and the author of Step Up or Step Out. He works with schools, organisations and leadership teams around the world. To enquire about a keynote, workshop or facilitated leadership session, email jonno@consultclarity.org.

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