Rachel Skerritt Named Headmaster of Boston Latin School

Boston, March 23, 2017 – Boston Public Schools (BPS) Superintendent Tommy Chang announced today that he has chosen veteran school leader and former BPS chief of staff, Rachel Skerritt, as Boston Latin School’s 28th headmaster. Ms. Skerritt, who graduated from Boston Latin School (BLS) in 1995 and taught English at her alma mater, will become the first person of color and the third woman to lead the institution in its 382-year-history.

Ms. Skerritt, a Dorchester native who is currently the deputy chief of leadership development for the District of Columbia Public Schools (DCPS), was selected by a school-based screening committee that unanimously recommended her to Superintendent Chang.

“We would be hard pressed to find another educator better suited to lead Boston Latin School than Rachel Skerritt. Rachel’s passion for her alma mater, her deep familiarity with its traditions, and her commitment to equity make her uniquely qualified for this role,” Mayor Martin J. Walsh said. “We are grateful she has chosen to return to Boston and serve the students of our city.”

Superintendent Chang said Ms. Skerritt is the ideal school leader to advance the mission of Boston Latin and the ongoing work to make BLS a welcoming and inclusive learning environment.

“Rachel’s life and professional experiences are tailor-made to lead Boston Latin School into its next chapter of excellence and equity for all,” Dr. Chang said. “She is a champion of providing rigor and opportunities for every single student in her care, and she is someone who will not compromise when it comes to the education of young people.”

Michael O’Neill, chairperson of the Boston School Committee and a BLS alumnus, hailed the appointment of Ms. Skerritt, describing her as an “immensely qualified” lifelong educator who will move Boston Latin School forward.

“The entire Boston School Committee applauds the Superintendent’s appointment of Ms. Skerritt. We thank the work of the search committee, the BLS community and the Superintendent in finding this exceptional leader,” Mr. O’Neill said. “Ms. Skerritt, whose passion for education was instilled in her as a student at Boston Latin School, has succeeded at every step of her extensive career due to her focus on building a great culture, hiring and supporting a strong team, connecting with students and families, and being an excellent instructional leader. We are delighted that she is returning home to her city and her alma mater.”

After graduating from Boston Latin School, Ms. Skerritt attended the University of Pennsylvania, where she earned a bachelor’s degree in three years and received a master’s degree in education the following year.

In 1999, she returned to BLS as a 7th-grade English teacher, a role she expanded to include instructing English literature each year to 150 students in 7th, 10th and 12th grades. In 2006, she received the Crystal Award for excellence in teaching, an honor given out by the school’s students.

During her seven years teaching at BLS, she co-chaired its Faculty Steering Committee during a two-year strategic planning and self assessment process for accreditation from the New England Association of Schools and Colleges. The committee authored the school’s current mission statement. She also headed a subcommittee of “Optimizing Student Outcomes,” a group that worked to recruit and retain more Boston Public School students, particularly students of color.

Following a one-year principal fellowship in which she received administrative training and interned at Another Course to College (ACC), Ms. Skerritt was appointed headmaster of ACC in July 2007. While leading the BPS pilot high school for two years, ACC’s graduation rate increased by 11 percent, earning it a bronze medal from U.S. News and World Report.

In August 2009, then-BPS Superintendent Carol Johnson appointed Ms. Skerritt chief of staff. In addition to serving as the primary liaison between the central office, the Mayor’s Office and the School Committee, she also co-authored the district’s “Acceleration Agenda,” a five-year strategic plan.

Ms. Skerritt left Boston Public Schools in November 2010 to become principal of Eastern Senior High School. One of the oldest high schools in Washington, D.C., Eastern was significantly underperforming and had cycled through 13 leaders in 12 years before it was gradually phased out and reopened. Ms. Skerritt relaunched the turnaround school, recruiting a talented instructional team that instituted a new academic program for 300 9th-graders in August 2011.

Under her leadership, the school, which added one grade level of students each year and 40 additional staffers each spring, earned the second highest proficiency rate among comprehensive high schools in the District of Columbia Public Schools. By 2016, the school’s graduation rate soared to 79 percent – 10 points higher than the district average. That June, 85 percent of Eastern’s graduates enrolled in postsecondary institutions. Ms. Skerritt, who re-started the school’s theater program and launched study-abroad service-learning trips for students to Africa and the Caribbean, ultimately helped lead Eastern out of the equivalent of turnaround status in 2015.

While serving as the full-time leader of Eastern, Ms. Skerritt participated in the “Principal Ambassador Fellowship” with the United States Department of Education for two years. She was among a group of full-time principals chosen to be part-time advisors to Secretary Arne Duncan, convening focus groups to assess how the department can better support school leaders in an era of high-stakes accountability, and speaking nationally on the department’s behalf regarding turnaround schools, Common Core standards, and other key initiatives.

In June 2016, she was appointed deputy chief of leadership development for DCPS, overseeing the district’s professional development programs for school leaders and aspiring principals.

“I am incredibly excited to serve as headmaster of my alma mater, an institution that has shaped me as a learner and a leader,” said Ms. Skerritt. “I look forward to collaborating with staff, students, parents, alumni, partners, and the community at large to ensure that Latin School’s mission of college preparedness, and responsible and engaged citizenship is realized for all of our students.”

Michael Contompasis, interim headmaster of BLS, praised Ms. Skerritt as a talented, dedicated educator and skilled bridge builder.

“I was headmaster at Boston Latin School when I first met Rachel Skerritt as a newly enrolled 7th grader. Even at that young age, Rachel demonstrated extraordinary promise,” said Mr. Contompasis, who later, as BPS superintendent in 2007, appointed Ms. Skerritt to lead Another Course to College. “Exceptionally brilliant, passionate and thoughtful, Ms. Skerritt earned the reputation in Boston as someone you could always rely on for insight, vision, and good sense.”

Mr. Contompasis, who served as BLS headmaster from 1976-1998, said Ms. Skerritt’s ability to engage and inspire diverse constituencies sets her apart.

“She is masterful in bringing people together. But above all, she puts the needs of her students first,” he said. “As proud as I was to have appointed Rachel Skerritt to her first school leadership position, I am even prouder and more gratified today to turn the reins over to this exceptionally accomplished and dynamic educator – one who will undoubtedly have profound and lasting impact on the entire Boston Latin School community.”

BLS 10th-grade student Perrin Price, who served on the headmaster screening committee, lauded Ms. Skerritt for her student-centered approach. “Her beliefs and values in bringing direction to Boston Latin is just what this community needs,” she said. “I love how dedicated and committed she is. Just knowing that she wants to listen to students is so important. I believe that she will listen to us, and put our needs first. I am so excited to get to know her.”

Peter G. Kelly, president of the Boston Latin School Association, said Ms. Skerritt’s steadfast service to public education, her exceptional educational and professional experience and her longstanding devotion to the students and alumni of BLS make her an outstanding choice to lead the historic institution.

“A more successful preparation for the headmastership of Boston Latin School you will not find than in Rachel Skerritt’s extraordinary career. She is the right leader for this time and she would be an outstanding leader at any time for Boston Latin School,” Kelly said. “Rachel is a quintessential Latin School success story. She continues the strong tradition of exceptional leadership at the school and will no doubt elevate not only BLS but also the entire district through vision, aspiration, and confidence in the children of Boston.”


The Boston Public Schools (BPS), the birthplace of public education in the United States, serves nearly 57,000 pre-kindergarten through grade 12 students in 125 schools. BPS is committed to transforming the lives of all children through exemplary teaching in a world-class system of innovative, welcoming schools. We partner with the community, families, and students to develop in every learner the knowledge, skill, and character to excel in college, career, and life.