Cynthia Bertolini

Since the day that she graduated college, Mrs. Cynthia Bertolini says that her heart has been in education. 

“Whether I was working as a teacher or volunteering when I was growing my family, my heart has always been as an educator,” she says. 

When her daughter Luisa ‘20 started school at Oakcrest, Mrs. Bertolini was eager to get involved in the school community and throughout the last eight years, she has served in a wide variety of roles - from Director of Admissions to now as the Associate Head of School, as well as a Middle School mathematics teacher. In her new added role as Middle School Director, Mrs. Bertolini is excited to be working with the Middle School faculty. 

In her early years at Oakcrest, Mrs. Bertolini learned a lot about the school as a whole and she “quickly became an expert on all areas of the school and how it works,” she said, adding that her experience as a parent as well allowed her to “live the parent experience and hear about the student experience” from her daughter at home. 

“I gained a great appreciation for the faculty and curriculum and the entire formational program at Oakcrest, from the experience that the students have and the formation the parents receive,” Mrs. Bertolini said.

After four years in various administrative roles at Oakcrest, Mrs. Bertolini was eager to get back into the classroom, but she says that at first she was a little unsure where would be the best fit. When there was an opening for a Middle School mathematics teacher, Mrs. Bertolini was the perfect person for the job. 

“This was a big turning point because I had been very eager to be more engaged with the students, to flex my teaching muscle again,” she said. “The last time I had been formally in a classroom was 1995 but it was so great to be back in the classroom.” With her graduate degree in economics, Mrs. Bertolini was aware of her aptitude for math and numbers, and to apply these things in the classroom once again, she was confident it was a great place for her to be. 

She sees her return to the classroom as a great way to “remain connected with the classroom in this role and in the roles of academics.” 

“It is key for me to be a member of the faculty as I lead the faculty,” she added. 

In her current roles, Mrs. Bertolini says, “It’s been a real pleasure to work with the team and get an even deeper understanding of and appreciation for the excellence of our academic vision, program, curriculum, and the absolute star-nature of our faculty.” 

“I’ve learned a lot over the last six months in this position,” she explains. “It’s exciting to collaborate with the directors and faculty and carry the vision of continuous improvement forward.”

Having seen Oakcrest through many years, Mrs. Bertolini says that one of the biggest things she has seen is the school “thrive through growth in numbers.” Going from around 150 students to now over 300, and in a brand new space, “the school has been given a different stage where Oakcrest can carry out their mission that has been lived out beautifully since 1976.” 

“Oakcrest has really stayed true to its mission through substantial growth,” Mrs. Bertolini said. “That hasn’t been easy and it hasn’t been linear, but Oakcrest has taken its mission very seriously in an uncompromising way.”