Little did she know how much more red she had in her future.

O’Brien, who has spent much of her adult life working at and serving St. Andrew’s, was honored by the school on October 18 at Homecoming and Reunion when she was presented with the Thomas Shaw Award for Service to St. Andrew’s.

In 2011, two years after earning her bachelor’s degree from College of Charleston, O’Brien returned to St. Andrew’s as Director of Special Events. In 2015, in conjunction with her 10th-reunion, she moved into the role of Director of Alumni Affairs. In that role, she recruited and built the modern Alumni Council and worked tirelessly to build connections across the world with St. Andrew’s alumni. 

In 2018, O’Brien and her husband moved across the country. Their family grew but her connection to St. Andrew’s never wavered, as she continued to serve as a class agent and member of the alumni council - and always a superb ambassador for the school. In the summer of 2024, they returned to Maryland and O’Brien to a red-adorned environment, now in a part-time role as Events Coordinator.

“As both a professional and volunteer leader, Madeline has been a catalyst of the spirit, pride, and connection that our alumni have with their alma mater,” said Head of School Robert Kosasky at the Alumni Awards Brunch where she was honored.  “We have no better servant leader or cheerleader in our Lion Pride.”

O’Brien’s Lion Pride was more than just an “at school” thing. It was around every dinner table and family gathering from before she enrolled until after she had begun working at the school. Her older brother, Jake ’04, was already at St. Andrew’s when she began in sixth grade and her sister, Abbey ‘08, joined a few years later. When she returned to work at St. Andrew’s, her brother Sam ’12 was a senior and her mother, Anne Wallace, was Chair of the Board of Trustees. 

“Having my family at St. Andrew’s made it really feel like home,” O’Brien said. “And it gave us a bond that’s still strong today.”

O’Brien saw first hand the power of service in the work her mother did as both Board Chair, a force behind the partnership with Christ Roi, St. Andrew’s partner school in Haiti, and establishing the Anne Wallace Fund for Service Learning. 

“What I’ve come to realize — and what I hope to encourage for everyone — is that giving back to this community isn’t just meaningful, it’s energizing,” O’Brien said. “Whether it’s through volunteering, donating, or mentoring — contributing to St. Andrew’s not only supports the next generation, but it feels really, really good. St. Andrew’s — and my parents — instilled in me a deep culture of service. My mothers’s example as Board Chair has always pushed me to lead with service first. That’s why I’m passionate about giving back to a place that has given all of us so much.”

In her time as a student, one teacher who left an impact on O’Brien was Gregg Ponitch, who she had for math her junior year.

 

“Gregg Ponitch always emphasized effort,” O’Brien said. “I wasn’t a strong math student, but he encouraged me and made a class I never expected to enjoy genuinely fun. He also has a passion for service — I still have so many great memories from our service trip to Chicago.”

 

In her time as an alumna and employee, what O’Brien has found most rewarding has been the Alumni Council, which she was a catalyst in creating.

 

“The Alumni Council has really grown and evolved,” said O’Brien. “It’s exciting to see the impact it’s making and to imagine where we’re headed next.”

 

With O’Brien involved, it is sure to continue its impactful work in helping shape the alumni experience.