Stephanie Santos spends her mornings in the lobby, greeting the athletes headed to the locker room and the scholars en route to the library. There’s 878 students at DHS, and she’s still learning all their names. However, after working in education for 15 years, Santos knows connecting with students is her strong suit.
Santos was hired as the new associate principal in July, six months after Rachel Chavier resigned from the position. Her primary responsibilities include test coordination (specifically AP, MCAS, and SAT), running lead teacher meetings, and professional development planning. But Santos also brings experience, enthusiasm, and local ties to the school’s leadership team.
The daughter of Portuguese immigrants, Santos was born and raised in New Bedford. She hopped between her parents’ house in the West End and her grandparents’ in the South End. She became close with the kids from both neighborhoods.
“One thing I took for granted as a kid, but really appreciate now, is how diverse the Southcoast is,” Santos said. “I’ve always been surrounded by rich traditions and communities, many different from my own. I was fortunate to learn from and experience the customs and perspectives of people from all walks of life. That blend of influences shaped who I am as a person and as an educator.”
Santos attended New Bedford High School from 2002 to 2006. She was a dedicated member of the lacrosse team, as well as the concert and marching bands. As a senior, she auditioned—and was ultimately chosen—to be one of two drum majors.
Her aspiration to rise in the ranks wasn’t necessarily surprising. “I always knew I was going to end up in a leadership position my whole life,” Santos said. “I always wanted to move up in any kind of group I was in or any job that I had. I want to bring my ideas to the table.”
In 2005, Santos led the Whaler Marching Band to victory at the New England Scholastic Band Association Championships. New Bedford hadn’t won the Championship since her freshman year.
After high school, Santos studied English and Secondary Education at Bridgewater State University. From there, she accepted a job as an English teacher at Wareham High School in 2010.
That wasn’t the only hat she wore, though. Santos had a stint with the yearbook club, became a class advisor, and tutored students in English. With funds from a grant, Santos established Wareham High’s SAIL program, an after school and summer enrichment initiative.
“I’m happy to say it grew over the years into a really successful program that lived on after I left Wareham,” Santos said.
Additionally, Santos served as one of Wareham’s four deans of students. She oversaw discipline and attendance—her first experience in administrative-type responsibilities.
“That position really showed me I like being part of decision-making,” Santos said. “Although it’s not so much affecting kids face-to-face every single day, I like being able to make decisions that are for kids and for their learning.”
By the time the COVID pandemic died down, Santos had been teaching for over a decade, earning her master’s degree from UMass Dartmouth along the way. She was ready to shift gears.
Thus, she went back to school, this time at the American International College. She received a Certificate of Advanced Graduate Study in school leadership. Soon after, in 2022, she took a job as assistant principal at Easton Middle School, half an hour upstate.
Her proudest accomplishment there, she said, was expanding Easton Middle’s restorative justice program.
Instead of punishing students for poor behavior with suspensions, expulsions, and typical disciplinary actions, restorative justice programs encourage students to develop social-emotional and conflict resolution skills while building relationships with staff members and peers.
“I was definitely a go-to [person] for a lot of kids,” she said. “That meant the most to me.”
Santos, however, never deleted her account on SchoolSpring—a job board for Massachusetts educators. Her inbox would fill up with job openings while she was working with Easton students. On the one day she didn’t ignore the emails, she saw the DHS position being promoted.
“I was like, ‘I’d love to work in Dartmouth,’” Santos recalled. “I really liked the position, because it was a step-up, and it involved a little more decision-making, which I was looking for.” Not to mention it was a much shorter commute for the New Bedford resident.
Moreover, her time at Easton Middle was a valuable precursor to becoming an associate principal. “I learned so much in my three years there that really prepared me for this position now,” she said. “Before that position, I wouldn’t have been ready for this.”
The relationship building aspect of administration that Santos enjoys is more challenging as an associate principal. When she was dean of students and an assistant principal, Santos was in charge of discipline and attendance, so she met with students regularly. The responsibilities of associate principal, conversely, reduce the amount of direct interaction with students.
“In this position I plan to do the same thing; it’s just in a different way,” Santos said. “So I have to figure that out.”
She added, “I’m glad to be back [working] in high school. I think that’s where my heart’s always been. At the end of the day, middle school and high school are just a different age group. They’re not that different as far as relating to kids.”
When she’s not at 555 Bakerville Road, Santos enjoys being active, reading, watching New England sports, and attending a wide variety of concerts, from country to rock to R&B. She also spends time with her four-and-a-half-year-old American Bulldog, Lady.
“I spoil her like she is my child,” Santos said. “She’s extra special to me because of how she came into my life. She sort of fell into my lap on the first anniversary of my mother’s passing from cancer. I was struggling a bit at the time, and she appeared at just the right moment. I named her Lady because my mom always playfully called me and many others senhora. Senhora in Portuguese translates loosely to ‘lady.’”
Santos travels to Portugal at least once every five to eight years. Her 89-year-old grandmother owns a house in the city of Figueira de Foz. Santos is planning a visit for next summer; until then, she’s back home in Bristol County, with the school year ahead of her. But she’s up to—and excited about—the task.
“I’m really happy to be working in the Southcoast again,” Santos said.
