WESTPORT — On her last day as a high school English teacher, Jennifer Allen said goodbye to her students and burst into tears — not because she was leaving, but because she was promoted to assistant principal and knew how dearly she would miss classroom teaching.

Allen joined the Westport Public Schools as the new director of secondary education last month. After earning a B.A. and a M.A.T., both in English, from the University of Vermont, Allen moved to Connecticut to teach the language she studied at Cheshire High School. She steadily rose her way up the ladder to assistant principal at Cheshire High School and then went on to be principal at Dodd Middle School and then Dr. Robert Brown Middle School.

When she went back to school to work on her doctorate at Columbia University’s Teachers College, Allen became a consultant for Engaging Schools. Upon completion of her coursework at Columbia, Allen worked for Hartford Public Schools, first as executive director of professional learning and most recently as chief talent officer where she restructured the human resources department into the office of talent management for a school system with 22,000 students and 2,000 employees.

Despite never having worked in Westport Allen has ties to both Superintendent of Schools Colleen Palmer and former Staples High School Principal John Dodig. Allen worked under Dodig when he was principal of Cheshire High School; one of Palmer’s sons attended Dodd Middle School when Allen was the principal there.

Dodig was a mentor for Allen and encouraged her to apply to work directly under him as the assistant principal at Cheshire High School.

"The new principal who said, ‘you really should think about becoming an administrator’ was John Dodig. We got this new principal and I didn’t know what I wanted to do and he said to me ‘you need to be thinking about being an administrator’," Allen said.

"So I did that for a year and a half and we had a wonderful time. He taught me a lot and he’s a fun person. We enjoyed the work," Allen added.

Adapting to change and taking on challenges is not something new for Allen. Less than two years into her job as assistant principal, the superintendent asked her to take over leadership of Dodd Middle School, halfway through the school year, after the principal was put on leave.

"The superintendent asked me on Thursday if I would be acting principal of the middle school on Monday," Allen said. "At first I was quite taken aback at the difference between standing in a middle school and working with high school students. Then I came to fall in love with middle school."

"I knew where they (middle school students) needed to go and John (Dodig) and I really worked hard on the transition to help kids move from a more protected environment to a more independent environment and we worked really hard at that…It was a magical time in terms of our working together," Allen said.

Looking forward, Allen expressed her support for the implementation of an advisory period — an initiative that her predecessor and current Staples High School Principal James D’Amico has been considering.

Ideally, Allen said groups of 10 to 12 students would meet a set period of time per week with an advisor in a more informal environment than class. Allen said this process would increase the chances for students to feel as if they are able to confide in that advisor. Moreover, she believes it would enhance the school’s understanding of individual students.

"There needs to be the niche for the personal contact," Allen said. "This is not going to solve all the ills, it just increases the likelihood that a student feels connected and I think that affective climate piece is really critical—it keeps people in the mix."

Allen feels her experience at all levels of secondary education and her Westport connection has thoroughly prepared her to take on the new job.

"I feel as if I’m coming home. I’m following John Dodig, I know his work. I know the commitment of this district to having high expectations and providing adequate support at the same time," Allen said.

I’m very familiar with issues related to school climate and culture. Middle school students are my peeps and high school is certainly my background. It just seemed like such an important fit for the next piece of the work that I am going to be doing and it just feels like a tremendously appropriate fit," Allen said.

@chrismmarquette/ cmarquette@bcnnew.com