Alumni Spotlights

Founders' Day marks 100 years of Dexter Southfield.

Chief Marketing Officer at Dunkin’ reflects on the significant impact of Dexter Southfield on her life.  

Campus came to life as we celebrated Reunion 2025.

Jordan Mason ’19 returns to campus to spend time with Boys’ Varsity Basketball during workouts.   

Director of Translational Science at Factor Bioscience found his passion for life science at Dexter Southfield.  

Recent graduates share their excitement for moving to college. 

Congratulations to Liza DeCaprio ’21, who has received the Lindsay Roemmich Sport Management Achievement Award at Rice University.

Congratulations to the Class of 2025! 

Entrepreneur James Morelli ’92 pays credit to his early education and lessons learned at Dexter Southfield.

Diksha Thach ’17, co-founder of GiveCard, credits Dexter Southfield for instilling strong values that have supported her entrepreneurial journey. 

Filmmaker and screenwriter Matt Brown ’85 spoke with Ms. Martin’s Upper School British Imperialism class about his movie, The Man Who Knew Infinity.

Will Vincent ’20 shared his passion for building electric guitars with Middle School students.

Alex Zook ’01 visited the Dexter Southfield Upper School Theater Department to assist in the Winter One-Act production of Nellie.

Over the course of her college years, Caoilinn has returned to campus during her breaks to assist the Admissions Office.

Addie Faggas ’18 studied business at the University of Alabama and now works for PROCEPT BioRobotics, a medical technology company. 

Brendan Walsh ’89 P ’28 is a Boston Police Detective, a former hockey player, and now a Dexter Southfield parent.

Kaity ’09 was drawn to Dexter Southfield after just one visit. She admired all that the School had to offer and immediately felt it was the perfect place for her to finish her Upper School years. 

Pat Daly ’16 is prepared for his future thanks to his Dexter Southfield experience. 

From preschool teacher to travel blogger, Caroline ’08 has had quite an interesting career path. Caroline turned her hobby into a full-time career that has led her to many global opportunities and partnerships.

Throughout his college experience, Sam '19 held close the lessons he learned at Dexter Southfield. Sam leveraged the resources available to him at School to kickstart his dream of pursuing a career in sports management.

Meghara '16 attended University of New Hampshire where she played on the Division 1 Women’s Ice Hockey Team for four years and served as captain her senior year.

Dylan Hayre '00 aspirations led him to a career in political campaigns and issue advocacy, working with candidates, coalitions, and communities to advance progressive ideas at the local, state, and national levels.  

Isabel Lord '15 attended Dexter Southfield for 13 years. Isabel's passion for journalism began as a student at the School. From there, she attended Georgetown University and now is the Assistant Editor for Forbes Magazine. 

Connor Bowman ’19 dedicates much of his success at Tufts University to being a student at Dexter Southfield.

Bissy Riva '14 is an oil painter and textile artist who creates abstract expressionist work consisting of painting, fabric manipulations, and pattern design. Bissy is currently practicing art in Nairobi, Kenya.

Annie Reardon ’11, co-CEO of Glow Labs, was recently listed in Forbes 30 under 30. The New York City-based company has climbed its way to success behind Annie’s leadership and her lessons learned at Dexter Southfield.

Jim Stamatos '82 grew up just down the road from Dexter Southfield. Jim is the proud parent of Zack '21 and Marcus '23.

Before becoming a part of the Vancouver Canucks organization, Jack ’18 proudly wore the shield for the Dexter Southfield varsity hockey team.

After attending Dexter Southfield through Class 8, Sitarah '22 attended Boston University Academy (BUA). While at BUA, she had a vision to create a mural on a building directly next to the BU Bridge.

For many Dexter Southfield athletes, their legacy continues well beyond their time at the School. Courtney Turner '12 is no exception.