Maya Smith started her professional career working in finance and business, but this daughter of educators eventually found her true calling in their world, where she has spent the last 21 years as a teacher and administrator in the Boston Public Schools.

The 45-year-old Dorchester resident, now the associate head of school at Fenway High School in Mission Hill, was named Assistant Principal of the Year by the Massachusetts School Administrators’ Association last month.

“It came out of the blue for me,” said Smith in a recent interview. “Mostly I don’t like awards, and I like to do my thing and avoid being on the radar. I like being behind the scenes and helping our young people thrive.”

Smith, who grew up in Roslindale, makes her home on Waldorf Street in the Ashmont-Adams neighborhood. She has been at Fenway High for six years, and before that, she worked at the now-closed Timilty Middle School, the now-closed Rogers Middle School, and the Condon School.

With the state award in hand, she is a candidate for the national School Administrators Association award, which is currently under review.

“Maya has profoundly shaped the way we do things at Fenway High School through her dedication to eliminating opportunity gaps and her commitment to Fenway’s core values: Work Hard. Be Yourself. Do the Right Thing,” said Head of School Dr. Geoffrey Walker.

“Fenway was a 2024 DESE School of Recognition, and Maya’s leadership in our school and of our Math and Student Support Teams plays a pivotal role in Fenway’s continued success,’ Walker added. “Her leadership is based in integrity and high standards, which she not only sets but also exemplifies through her hard work and passion for the well-being of our students, staff, and families.”

Smith started her career as a substitute teacher at the James Timilty Middle School in Roxbury. By her own admission, she had every intention at the time of steering clear of the education profession. Yet, after a stint at Merrill Lynch, she found that business and finance wasn’t her calling. She was thinking about nursing when her dad suggested she substitute teach to earn some extra money.

“I landed a long-term sub position in a special education class and that’s where I really learned I loved teaching,” she said. “I was learning more from the kids than they learned from me, and they helped me a ton and I loved making sure students were able to be successful and thrive after high school graduation.”

Maya Smith, associate head of school at Fenway High School, celebrates outstanding MCAS math scores this past year with students Miguel Hilario, left, and Camio Mendoza. BPS photo

In addition to that position, Smith has served in other roles over the last two decades, including time as an advanced work teacher. She came to Fenway High as the director of special education and advanced to associate head of school three years ago.

At the high school administrative level, she finds it’s invigorating to guide young people to success and make school-wide impacts. “I feel like middle school will prepare you for everything,” she said with a laugh.

“What I love about high school is we’re able to have conversations. I see students come in at ninth grade not knowing where they will be in four years. I love that I’m able to help them create a pathway in that time to ultimately end up at a four-year college.”

Fenway High has an enrollment of about 390 students in grades 9-12, with most coming from Dorchester and Roxbury. One of the first high schools in Boston to offer “early college,” it is aligned with Wentworth Institute of Technology and UMass Boston for the early college pathway, allowing any student without restriction the ability to take up to 15 college credits while in high school.

Smith noted that 95 percent of students graduate with at least one early college credit at the school.

“I’m very passionate about serving my community and I really think every student deserves an opportunity,” she said. “That is our job, and the work is not easy but very rewarding knowing that students are leaving able to contribute to our society in positive ways. I love what I do.”