'A difficult situation.' Pittsfield schools looking to fill two principal jobs, interim superintendent role

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On Monday, the district advertised for a principal at Herberg Middle School, with the goal of a multiyear contract, and reposted an opening for director of special education.

PITTSFIELD — The city school district is looking to fill at least four key leadership positions by this summer, including two principal slots at schools undergoing significant changes and challenges. On Monday, the same day Pittsfield High School Principal Maggie Harrington-Esko announced she plans to step down , the district advertised for a principal at Herberg Middle School and reposted an opening for director of special education. And the district is in the middle of hiring an interim superintendent to replace Superintendent Joseph Curtis who announced that he will resign as of June 30.

While Curtis noted that all building principals are important, PHS and Herberg both face significant challenges. Pittsfield High is working to restore its reputation following the arrest of a dean of students on cocaine trafficking charges, and a bruising series of allegations alleging inappropriate conduct by two additional administrators and two former educators. Yet, PHS remains one of the city’s best-regarded schools for its wide variety of advanced placement offerings and electives.



Herberg, meanwhile, is awaiting a significant citywide middle school restructuring, proposed to take effect in the 2026-27 school year. A committee has proposed changes in grade levels and curriculum to improve Herberg and Reid’s academic performance and address concerns about problem behaviors. The district will hold public meetings on the plan at 6 p.

m. April 29 at Herberg, and 6 p.m.

May 5 at Reid. School officials say much of the district’s outmigration through school choice has come in the middle grades, with some students returning to PHS or Taconic for high school. In a letter to families, Curtis said the district’s goal for Herberg is “to identify a strong leader who is aligned with the vision and needs of the Herberg community and to offer that individual a three-year contract that promotes sustained progress and stability.

” Herberg Principal William Wood, who has served since 2023 under a pair of one-year contracts, told The Eagle he plans to reapply for the position. The posting for Herberg 's principal seeks “an adaptive and innovative educator to close the opportunity gap, empower educators and maximize learning for all students.” It seeks applicants with “a proven track record in instructional leadership resulting in strong academic gains,” and “demonstrated experience in diversity, equity and inclusion practices.

” In a letter to Pittsfield High School staff, Curtis widely praised Harrington-Esko for serving the high school for 18 years “with incredible dedication, passion, and integrity,” and for stepping up to the principal’s office in 2022, when a search for former Principal Henry Duval’s successor proved unsuccessful. “We are incredibly grateful for her unwavering commitment to our school community, and we look forward to continuing to work alongside her as she finishes the year strong and helps support a thoughtful and smooth leadership transition,” Curtis said. “As I have shared with Maggie personally, she is truly one of the most courageous and resilient leaders I have had the privilege of working alongside," he said.

"She has faced recent circumstances and challenges, alongside all of you, that many — if not all — would consider impossible, and she has done so with unwavering strength, grace, and integrity.” Harrington Esko, who stepped down of her own accord, did not return a message seeking comment. The district had earlier advertised for a special education director to succeed Stefanie Wondriska-Clark, and appointed a committee of staff and community members to review applicants for that position and for a district director of social and emotional learning.

Wondriska-Clark was appointed on Aug. 23 of last year after serving six years as Pittsfield’s out-of-district special education coordinator. Before that, she was the director of student services for the Central Berkshire Regional School District.

She succeeded Jennifer Stokes, who is now assistant superintendent for school transformation and accountability. While the committee has closed in on a candidate for the social and emotional learning position, it has also decided to keep the special education position open, Curtis said. That hiring will require School Committee approval.

“They did one round of interviews and didn’t feel comfortable bringing anyone forward, so they asked we repost the position until it is filled,” he said. Meanwhile, the School Committee has received five applications from persons interested in serving as interim superintendent when Curtis steps down on June 30. The next step in hiring a new interim leader for the district is reviewing the applications to verify the candidates’ qualifications and licensure, School Committee Chairman William J.

Cameron said. “Then we have a couple steps we have to go through,” Cameron said. “We have to decide whether to interview all five candidates, assuming they’re all licensed.

We also have to publicly develop questions for the candidates.” As the School Committee does not have a regular meeting scheduled until April 30, and has two-and-a-half months before Curtis steps down, Cameron expects special meetings will be needed to accomplish the work. The responsibility for hiring principals lies with the superintendent’s office.

Curtis said two of the district’s assistant superintendents will oversee the hires — Matthew Bishop at PHS, and Jennifer Stokes at Herberg. Curtis told PHS faculty members that Bishop would reach out to staff and families on forming a Principal Hiring Committee, saying it "will play a vital role" in selecting a new leader. Neither Curtis nor Cameron are certain that an interim superintendent will be on board in time to provide input on the hires.

But Curtis said guidance from hiring committees made up of PHS and Herberg families and staff will "100 percent” be reflected in his decision. “This is a difficult situation,” Cameron said. “Replacing principals is a very significant move and the short time that remains between Mr.

Curtis’ leaving the district and new the interim superintendent coming on will not leave a lot of time to do a great deal of work on this." “I’m hopeful that we will find strong candidates and that we will have leadership teams at those schools that are effective for the new school year,” he said..