Words and photos by Linda Conner Lambeck

WESTPORT–The 2026-27 school year kicked off for teachers on Monday with a convocation program held in the newly renovated Staples High School auditorium.

The only time the lion’s share of the district’s thousand-plus staff members are in the same place at the same time, it was an opportunity to 

• Introduce staff members – some 62 individuals
• Announce the district’s 2027 Teacher of the Year, literacy coach Jessica Carey, and 
• Hear Superintendent of School’s Thomas Scarice lay the groundwork for what to expect in the new school year.

He predicted it will be a year of change driven largely by district work to adapt to the evolving impact of Artificial Intelligence.

What’s Coming

Scarice, who just sent his youngest child off to college, gave staff the same advice he said he gives his own kids:

• Figure out your focus,
• Figure out what it means and then,
• Figure out how to do it.

“It’s about frame of mind,” Scarice said.

The focus for the school district, according to the superintendent, will be preparing students for change that is still evolving.

“We are kind of in the middle right now,” Scarice said. “We have a moral imperative to prepare kids for that world.”

AI, more than a year ago, was made part of the district’s strategic plan.

Scarice calls AI a force multiplier, something that can radically increase effectiveness, but added that it must be pursued with caution.

Part of the work of staff involved in the district’s AI model involves building guardrails to ensure technology is serving the district and not the other way around.

“We have to balance it out,” Scarice said. “My focus here is to increase capacity.”

Teacher of the Year

Chosen from among two dozen nominees, Westport’s 2027 Teacher of the Year, Jessica Carey, entered the district as a brand new teacher in 2005.

Carey told the crowd she did not get to this point in her career alone and that if she’s learned anything, it is that teaching is not about having all the answers.

“What I know for sure is this: teaching is an art,” said Carey, a literacy coach based at Saugatuck Elementary School. The first part of her career was spent as a classroom teacher at Kings Highway Elementary School.

She described her job as more than helping to improve reading skills but also making sure colleagues and students feel seen.

“Eleven years ago, when I interviewed for my role as a literacy coach, I told the committee that I had a dream about what schools could look like,” she said. She envisioned classrooms where curiosity drives teaching and learning and growth is continuous.

“That dream still energizes me every morning,” Carey said.

She described working with fifth graders to help them become fantasy writers. They took to it so well they lined up after recess in hopes of getting more time to write.

Two summers ago, when district climate survey data suggested students weren’t telling their parents what they learned at school, Carey decided to do something about it.

“I wanted our classrooms to create the kind of excitement that spilled into dinner conversations,” she said.

She said she leaned into curiosity, had third graders write the principal asking for more books and suggesting topics to explore.

As a result, classroom libraries were restocked with an array of nonfiction books. Some of those books found their way home because students wanted to share them with their families.

Great schools are not about finding a perfect formula, Carey said, but noticing what is working and helping it grow.

The best teachers, she added, are those who remain open to revising, listening and wondering.

“Twenty-one years ago, I stared at a blank page and wondered what I believed in. I thought my job was to fill it in. Now I understand that the page was never meant to be finished,” Carey said.

Saugatuck Principal Beth Messler said Carey’s vision is very clear and credited her with helping the district become a beacon of literacy in the state. The percentage of Westport students achieving proficiency in literacy is among the highest in the state.

Carey is also a responsive classroom trainer, helping Westport integrate social-emotional learning principles into how classrooms are run, according to Messler.

Another colleague said Carey doesn’t just teach, but builds a stage and then hands the microphone over to kids and to staff.

She also mentors new teachers and is a social-media influencer, posting a daily Instagram post called EyeOnLiteracy.

“She works each day to make our school a place where every student feels like they belong,” Messler said.

 Carey will go on to represent the district at the state level.

What’s new

Treated like a pep rally, the opening event included a warm up by Staples jazz band members during a courtyard breakfast, cheers by the Staples cheer team, and the National Anthem sung by Staples choral students. Scarice called 44 district custodians and maintainers in attendance up to the front of the stage to a standing ovation.

Assistant Superintendent John Bayers not only introduced 62 new staff members but listed scores of district employees who have served 20 years or more with the district. Four have been with the district 35 years or more. They include: Laura Blair, Barbara Ellertsen, Enia Noonan and Kathryn Sicbaldi.

The new staff members include 31 teachers and roughly the same number of non-certified staff.

Linda Conner Lambeck

^{_{Linda Conner Lambeck covers education for Westport Journal. She was a reporter for more than four decades at the Connecticut Post and other Hearst publications. She has covered education throughout Fairfield and New Haven counties. She is a proud member of the Education Writers Association.}}