Shaker Lane Building Project Update
Superintendent Search
Superintendent Finalist Interviews
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Superintendent Search Updates
After 15 years of service to our town, Littleton Superintendent Kelly Clenchy has announced his intent to retire. The Littleton School Committee has been tasked with finding a suitable replacement before the 2026–27 school year begins. In November 2025, the School Committee appointed members Sean Aherne and Elaine Santelmann to the Superintendent Search Subcommittee. In December 2025, Littleton engaged the Massachusetts Association of School Committees (MASC) to ensure an efficient hiring process for all involved.
In January 2026, after receiving overwhelming public interest, the School Committee appointed a Screening Committee, which represents many stakeholder groups. The Screening Committee is tasked with interviewing semi-finalists from the applicant pool and recommending a slate of three to four candidates to the full School Committee.
The Subcommittee surveyed Littleton residents to gauge the town’s priorities for a new superintendent. The results of this survey are shown below. Overwhelmingly, Littleton residents shared they’d like a strong collaborator who builds relationships and trust. They’d like the district to prioritize student well-being and mental health first, then student achievement and instructional leadership and DEI. Experience level is less important to them than leadership qualities, but prior superintendent experience, assistant superintendent, or central office leadership experience is a plus. Additionally, the town is looking for a strong communicator, someone who can lead by example to shine a light on our schools.
The Superintendent Search Subcommittee held a public forum on January 15, where residents were invited to share their thoughts on what is going well in the district, what needs to change, leadership qualities, and other comments.
In partnership with MASC, Littleton created a brochure for applicants to better understand our town and the community’s expectations for the next superintendent. Applications for Littleton Superintendent opened February 2nd and closed February 27th.
The Screening Committee met four times in March to screen applicants, agree on questions to be asked of all candidates, and conduct semi-finalist interviews. Please note that these deliberations were held in executive session out of respect for applicants.
On March 23rd, a list of four finalists were presented to the School Committee. After a full School Committee vote, the four finalists were accepted and advanced to final round interviews. One of the finalists withdrew before public interviews commenced.
Finalists will each had a “Day in the District” where they met with Littleton’s stakeholder groups during the day, held a community forum in the afternoon, and then had a public interview with the School Committee at 7 PM.
Charles Caliri
He is currently an Assistant Superintendent in Ayer-Shirley. Mr. Caliri holds a Bachelor of Science from Boston College, a Masters of Education from the University of Massachusetts, and is currently in progress on a Doctorate of Education from the University of Massachusetts. He also holds multiple leadership certificates as well as licensure from the Commonwealth in Assistant Superintendency and Superintendency.
Michael Caira
He is applying from Ashland, where he is the Assistant Superintendent of Curriculum, Instruction, and Assessment. Dr. Caira holds a Bachelor of the Arts from Assumption College, a Masters of Education from Fitchburg State University, and a Doctorate of Education from Boston College. He also holds multiple additional leadership certificates as well as licensure from the Commonwealth in Assistant Superintendency and Superintendency.
Kate Guziejka
She is currently the Principal of the Spaulding Memorial School for the North Middlesex Regional Public Schools. Ms. Guzeijka holds a Bachelor of the Arts from the University of Massachusetts, a Masters of Education from the University of Massachusetts, and a certificate of School Management and Leadership from the Harvard Business School. She also holds multiple additional leadership certificates as well as licensure from the Commonwealth in Assistant Superintendency and Superintendency.
The School Committee is expected to appoint the next Littleton Superintendent on Thursday, April 9th. This meeting will take place at the Center on Shattuck, beginning at 7 PM. The public is welcome to attend. The new Superintendent will begin their service on July 1, 2026.
Questions? Get in touch with the Superintendent Search Subcommittee:
Email Sean Aherne