Assistant Superintendent for Curriculum, Instruction & Accountability
Winthrop Public Schools
Ms. Gallivan is a strong advocate for professional learning among Assistant Superintendents.
Lori A. Gallivan has travelled a winding road through a variety of roles and communities to her current position as Assistant Superintendent for Curriculum, Instruction & Accountability for the Winthrop Public Schools. As she reflects on the journey, she is grateful for the experiences, colleagues, and lessons that have shaped her along the way.
Like several other district leaders in this series, Lori said that her original career goal was not to become an educator. After graduating from Easthampton High School and Westfield State University, Lori planned to go to law school, but with the popularity of television shows like L.A. Law at the time, the job market was flooded with aspiring attorneys. As Lori considered other options, an unexpected opportunity arose: One of her favorite high school teachers told Lori she was going on leave and asked if she would substitute for her.
Fresh out of college, Lori got the temporary job and quickly immersed herself as the newest faculty member at Easthampton High School. She taught sections of World History, Economics, and Junior Achievement Business Basics, managed the school store, advised the senior class and Mock Trial Team, and chaperoned a class trip to Disney World.
“I just fell in love with the whole thing,” Lori recalled, “not just being in the classroom and teaching, but what it meant to be an educator and what role you had in the lives of kids.”
The experience marked the beginning of a career in public education spanning more than 30 years. After the long-term substitute position, Lori went on to work as a physical education teacher and the first 504 Education Plan coach at Westfield High School. She later taught incarcerated boys in a maximum-security facility in Springfield through the Robert F. Kennedy Children’s Action Corps.
Becoming a School and District Leader
Eventually, her aspirations to become an administrator brought Lori to Eastern Massachusetts, working in various school and district leadership roles in Lynn, Newburyport, and Saugus. During that time, she earned a Master’s degree from Cambridge College. While she was serving as Executive Director of Curriculum, Instruction & Accountability for the Saugus Public Schools, Lori was contacted by her former colleague, Lisa Howard, who had recently been hired as Superintendent of the Winthrop Public Schools. In July 2018, Lori accepted Lisa’s invitation to join her in Winthrop as Assistant Superintendent.
“It’s been a great ride,” said Lori. “All along the way, I’ve had great mentors, great leaders who have not just mentored me and helped me become a more well-rounded leader and educator, but they’ve also given me opportunities, and they’ve opened doors for me to be a part of the bigger picture.”
Like many Assistant Superintendents, Lori has a broad range of responsibilities related to teaching and learning, curriculum, assessment, professional development, certification, information technology, and much more, including extensive reporting and compliance obligations. Lori said she is proud of the team she has helped build and support over the past seven years, and together with Superintendent Howard, they are charting a successful course for the Winthrop Public Schools.
Lori said she has grown as an educator and leader during her career in part by developing active listening skills. She said she has learned that when adopting a new curriculum or other significant change, it is critical to listen to the questions, concerns, and ideas of everyone involved – “but not to listen with your mind already made up,” she said.
“The hardest part is that change is pain,” said Lori. “I always want to support teachers as we’re making these changes. It’s always on my mind to put myself in the place of these teachers, because that’s important to the success of these initiatives.”
Engaging at the State Level
Lori is passionate about giving Assistant Superintendents meaningful opportunities for professional growth and development. For more than a decade, she has been active in M.A.S.S., including participating in the Assistant Superintendent Mentor Program and Affinity Groups.
She said, “The leaders I’ve worked with had have not just allowed me but encouraged me to get out and be part of these things. I really hope that more Superintendents continue to do that. There are a lot of people who love this role and have a lot to offer.”
For the past 11 years, Lori has served on the M.A.S.S. North Shore Roundtable, a group she described as “incredibly inclusive of Assistant Superintendents – always making us active participants, never second-class citizens.” Lori has also served for eight years on the M.A.S.S. Professional Development Committee, and she is deeply involved in planning the Paul J. Andrews Executive Institute each summer.
The addition of a M.A.S.S. listserv for Assistant Superintendents, she said, has been a “game-changer,” especially for her colleagues newer to the role to be able to get critical guidance and advice from more veteran leaders.
In 2020, Lori participated in the Rennie Center’s Massachusetts Education Policy Fellowship, which she described as “an eye-opening experience,” in part because of the engagement with a cross-section of leaders from the public and private sectors in learning about education policy.
In recognition of her work, M.A.S.S. presented Lori the 2023 Assistant Superintendent Leadership Award.
Looking Ahead
Lori cherishes her time at home and traveling with family and friends. She and her wife Sharon live in Saugus, and Lori has two grown stepchildren. Last month, the couple welcomed their first grandchild. Lori said she has a large group of friends she met playing softball many years ago, and they remain part of her extended family today.
So what is next professionally?
“For a long time I had aspirations to be a Superintendent, and participated in a few searches, but then I got to a point where I said, I really love what I do here,” said Lori. “When I was younger, I felt like I was missing out by not taking that next step, but there’s so much to be said for really knowing that you’ve found your place.”
She said she would consider the Superintendency only if she were asked to succeed Lisa Howard after her retirement.
“Consciously, I’ve made the decision that I’m going to stay in Winthrop,” she said, “And if it becomes that I step in for Lisa after a couple of years, then great, but I believe in what we’re doing and the track that we’re on.”
Shortly before the holiday break, while reading Frosty the Snowman to elementary students, Lori said she felt a strong sense of being in the right place.
“You’re looking out at those faces and seeing the excitement,” she said. “That’s when I know I’m where I’m supposed to be.”
