A look back at 16 years of Heart and service


Claire Moore '22

Mr. David Olson’s 16 years at Sacred Heart Greenwich come to a close.

Mr. David Olson will say goodbye to the Sacred Heart Greenwich community at the end of this academic year.  After 16 years of service as Head of Middle School, he will assume a new leadership opportunity as Executive Director at Waterside School in Stamford, Connecticut.  Senior lifers Dominique Prato and Yvestlana Lafontant reflected on their time with Mr. Olson and his greater impact on the school community.  Additionally, Mrs. Samantha McCoy, Middle School History Teacher and Department Chair, who worked alongside Mr. Olson to promote a welcoming school environment, spoke about his devotion to his students.

Mr. David Olson speaking at Middle School Prize Day.  Courtesy of Sacred Heart Greenwich Communications

Mr. Olson attended John Jay High School, located in Katonah, New York.  He graduated from Gettysburg College, where he earned a Bachelor of Arts degree in Sociology and Anthropology.  Following his undergraduate education, Mr. Olson received his Master of Arts in History from Western Connecticut State University.  Mr. Olson began his teaching career as a History Teacher and Eighth Grade Dean at Hackley School in Tarrytown, New York, where he worked for 13 years.  He then served as Head of School at Applewild School, a boarding school in Fitchburg, Massachusetts.  In 2005, Mr. Olson joined the Sacred Heart community.

Throughout his time on King Street, Mr. Olson dedicated himself to enhancing all aspects of Sacred Heart education.  He especially focused on making students feel heard, known, and safe while at school.  In addition, he wanted students to develop their writing, public speaking, collaborative, analytical, and innovation skills in Middle School.  Alongside the Middle School faculty, Mr. Olson strove to create the best possible school-wide writing process outline for all students to follow, implemented a Middle School musical, and expanded the arts programs and athletics offerings.  He also formed a Robotics Team and furthered the computer science and programming curriculum for Middle School students.

Dominique has been a member of the Sacred Heart community for 15 years.  She recalled a memory that embodies Mr. Olson’s enthusiastic and welcoming personality as an educator.  

“As a rising fifth grader, I was nervous about entering middle school,” Dominique said.  “I expected that on the first day of classes, none of the Middle School faculty would know my name, Mr. Olson approached me in the hallway, and to my surprise, addressed me by my name and then began to ask me about my first day in middle school.  It was a moment like this that truly emphasized Mr. Olson’s desire to make all his students feel welcomed and included in the Middle School community.”

It was a moment like this that truly emphasized Mr. Olson’s desire to make all his students feel welcomed and included in the Middle School community.”

— Dominique Prato '21

Yvestlana expressed her gratitude for Mr. Olson’s genuine care and concern for each of his students.  

“For years, Mr. Olson has continually lived by his motto ‘never worry alone’ and it has been deemed true when students would feel stressed or overwhelmed about their school work or their personal lives,” Yvestlana said.  “Personally, Mr. Olson has been there for my family and me.  He always saw to it that he did everything he could to support us, and we will never forget the things he has done for us.”

Mr. David Olson welcomes a student at the beginning of this academic year.  Courtesy of Sacred Heart Greenwich Communications

Mr. Olson further supported his students through monitoring Sacred Heart’s Diversity, Equity, and Inclusion efforts for many years, along with expanding wellness initiatives and participating in the 2019 Civil Rights Pilgrimage and a Network Summer Service project called “Hearts Fighting Hunger.”  For two years during his time at Sacred Heart, Mr. Olson served as Assistant Head of School.  

After 16 years of working together, Mrs. McCoy spoke about Mr. Olson’s strengths in many aspects of his career. 

“Mr. Olson’s impact on Sacred Heart in general, and our Middle School specifically, is really difficult to quantify or summarize because it’s so wide-ranging,” Mrs. McCoy said.  “From his first day on our campus, it was clear that he took our mission seriously and was willing to do whatever he needed to do ‘for the sake of a single child.’  He has also been a master at hiring excellent teachers and building a strong set of faculty.  I can say for certain that he helped shape me into the successful teacher that I am today, always encouraging me to try new strategies and methods for my classes.  He will be dearly missed in our community.”

Mr. Olson made a special impact in Yvestlana’s life, just as he did for many other members of the school community.  Yvestlana expressed her gratitude for Mr. Olson and all that he has done for Sacred Heart.

“The Sacred Heart community will definitely lose one of its best,” Yvestlana said.  “I wish you and your family all the best, Mr. Olson.”

Featured Image by Claire Moore ’22