
By John Schwing
WESTPORT — The new principal of Coleytown Middle School is not new to the Westport school district.
Parthena “Penny” Proskinitopoulos, an assistant principal at Staples High School for the last two years, was unanimously appointed the new Coleytown Middle principal by the Board of Education at a special meeting Wednesday morning.
She succeeds Kris Szabo, who retired at the end of the last academic year.
Proskinitopoulos was chosen after a “rigorous” selection process, Supt. of Schools Thomas Scarice told the online meeting. “For the past two years,” he said, “she has done remarkable work” at Staples, “developing relationships with faculty, but really with students and families.”
Scarice added that Proskinitopoulos also struck “an incredible balance” between being an instructional leader and “someone who truly subscribes to the type of culture that we are working to continue to establish in our schools.”
Board Chairwoman Lee Goldstein said that she and other board members who interviewed Proskinitopoulos for the Coleytown post were impressed with “your warmth and your genuineness and your real commitment to students, families and staff.”
Officials are confident the new principal will make the Coleytown community “even better than it already is,” Goldstein said.
Proskinitopoulos, in brief remarks to the meeting, said, “I’m so thankful and appreciative of this opportunity,” and promised to “continue to do due diligence and work really hard for the students and families at Coleytown.”
Proskinitopoulos began her career in 2006 as a middle school social studies teacher in Fairfield. In 2014, she became a technology integration specialist, and in her final year with the Fairfield school district, was the interim assistant principal at Roger Ludlowe Middle School, according to a statement from Westport school officials.
She was hired in 2021 as a Staples assistant principal, where the officials’ statement cited “her exemplary work as the administrator in charge of the Response to Intervention program.”
Proskinitopoulos holds a bachelor of arts degree in psychology from St. John’s University, a master of arts degree in teaching and a sixth-year diploma in educational leadership from Sacred Heart University.
She also has a doctorate in educational leadership from the University of Bridgeport.
John Schwing, the Westport Journal consulting editor, has held senior editorial and writing posts at southwestern Connecticut media outlets for four decades. Learn more about us here.


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