New Milford hires new assistant superintendent and high school principal



NEW MILFORD – The district school board appointed a new principal for New Milford High School and a new deputy principal at a regular meeting on Tuesday evening.

Holly Hollander, the former director of programs and education in Lebanon, has been hired as the next deputy district superintendent. Raymond Manka, former principal of Stamford High School, has been hired as the next high school principal.

They will begin their new roles on or around July 1.

Manka will take over from Greg Shugrue as Shugrue leaves the district to become the new principal of Gilbert School. Hollander will fill a position held by Acting Assistant Superintendent Catherine Calabrese.


“I am delighted to welcome Ms. Hollander and Mr. Manka to the New Milford Public Schools administrative team,” Superintendent Alisha DiCorpo wrote in a press release sent out early Wednesday morning.

She said the two candidates “shape through their actions and express the importance of collaboration and effective communication.”

The press release detailed the two educators’ backgrounds, including Hollander’s work in “program redesign and alignment on assessment review and data management.”

She previously held various administrative positions across the state, including as Director of Educational Programs at the CT Science Center, Director of the Mandell Academy for Teachers, and as Director of Teaching and Learning and Teaching. K-12 common senior supervisor for Cromwell Public Schools.

Hollander’s experience includes serving as an instructor at Central Connecticut State University for elementary education, and as director of student education and field experience for nearly 10 years.

In addition to her administrative roles, Hollander worked as a third and fifth grade teacher.

Hollander holds a bachelor’s degree in education from Illinois State University and a master’s degree in elementary education from Central Connecticut State University.

Manka comes to New Milford from Stamford, where he has been a High School Principal since 2015. During his career he has also served as Deputy Principal of High Schools in several districts including Stamford, Norwalk and Westhill.

Manka’s first teaching roles were as a sixth grade science teacher at Bridgeport and a biology teacher at both Jonathan Law High School in Milford and Ridgefield High School. He holds a bachelor’s degree in elementary education and biology from Western Connecticut State University and a master’s degree in education from the University of Bridgeport.

Hollander’s new position has not been filled for some time, and the board has been looking for a full-time replacement since December 2020.

Previously, DiCorpo served as Acting Assistant Superintendent and then Acting Superintendent in 2020 before being hired as the new Superintendent earlier this year. When she stepped down as Acting Assistant Superintendent, the board chose Catherine Calabrese to fill the position until they could find a new hire.

At the time, Calabrese was deputy principal of Northville and Schaghticoke elementary schools, and her appointment as acting deputy superintendent required a job shake-up to cover the vacancies.

In the press release, DiCorpo went on to describe the new hires as “thoughtful educators who will continue to build on the great work already started in their respective positions.”

“I can’t wait to work alongside them as they begin their work in the district. “



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