Excellence in Academia: Meet Our Alumni Leaders in Education

For nearly 45 years, Prep for Prep has proven that access to a quality education can change the trajectory of one’s life. More than 600 alumni who have benefited from the Prep experience are shaping the next generation of learners through their work at primary and secondary schools, colleges and universities, and education-related nonprofit organizations. Meet three Prep alumni — José De Jesús (IX), Xiomara Hall (P9 I), and Ramón Javier (XI) — who were appointed to senior leadership positions at independent schools during the 2021-2022 fiscal year and learn how Prep has influenced additional alumni leaders in education.

During the first summer of Preparatory Component, students are assigned to one of two subschools. For decades, these cohorts were named after Johnny Gunther, Jr. and Anne Frank, two young people whose lives were too short for their full promise to be shared. In the summer of 2022, these groups were renamed to honor two Prep alumni. José De Jesús (IX) is one of them. (Natalie Swaby Hutchinson (XIV) is the other.) “I felt like I was literally flying in so many ways and just blown away by that honor” says José, who received the news while training to fulfill his childhood dream
of becoming a pilot. “I’m deeply humbled. I want to continue to make the program proud and make those kids proud. That’s a big inspiration for me.”

The naming honor reflects José’s professional accomplishments and impact on the Prep community. An educator for more than 20 years, he became the first Prep alum to be appointed head of an independent school when he joined Lake Forest Academy, a boarding school in the Chicago area, in 2019. This July, when he stepped into the head of school role at The Dalton School, he became the first person of color to hold the position in the institution’s 103 years.

“I feel enormous pride, excitement, and energy,” says José of his Dalton appointment. “There is symbolism to it, not only for Prep, which has had such a long and successful relationship with Dalton, but also for people of color in general and Latinos specifically. I’m open-eyed about the particular challenges that will come with that. My failures and successes will translate more broadly.”

At six years old, José came to New York City from Puerto Rico with his mother, an English teacher pursuing a doctorate at New York University. Despite his mother’s best efforts, José spoke very little English at the time. “It’s a lot more complicated teaching your own children,” acknowledges the father of two. “I can empathize with her frustrations with my language acquisition.”

It wasn’t long before José gained a command of English and began to excel as a student at P.S. 75. His strengths in reading and comprehension drew the attention of his fifth grade teacher, who nominated him for Prep for Prep. In the 14-month Preparatory Component, “my inner nerd got to play without fear,” says José. The program also opened his eyes to the impact of disparities. “It was a powerful lesson early on of what happens when you give people with talent an opportunity.”

As one of eight students from the same contingent to enroll at Horace Mann, José had a supportive network to help him navigate the differences that existed between kids like him and his affluent classmates. He recalls having to take the One Train to campus each day, while many of his peers could afford to take an express bus that got them there in half the time. “We needed the support of each other and of Prep to be able to connect to students who had had the privilege of being in independent school environments since kindergarten. The delta was pretty significant.”

José’s childhood experience creates an opportunity for him to have a special bond with Prep students currently at Dalton. At the opening assembly of the school year, José mentioned that he was a proud member of Prep, a statement that garnered a positive reaction from the Prep students in the audience. “After the talk some of the students came and sat down on the couch in my office and we had a chance to talk and connect. That was really lovely.”

It is this type of interaction with students that made José fall in love with the idea of being a school administrator. In his early days as an educator, he imagined a long career as a history teacher. That changed when he was tapped to be a leave-replacement dean while at Poly Prep. “I had this ratty black couch in my office and my students would come through to talk. I just loved that work. That helped me become even more interested in how I could have an impact on a broader level.”

After more than half a decade at Poly Prep, José spent five years as the Head of Upper School at The Packer Collegiate Institute before moving to the midwest to lead Lake Forest Academy. The advent of the Covid-19 pandemic fostered a strong desire to return to his hometown. José describes joining Dalton as a full-circle moment.

He will spend the first year in his new role grounding himself in the culture and traditions of the school, its educational philosophy, and its diversity work. He is also focused on bringing the school community back together. “We haven’t had a lot of time over the last few years as a community to gather,” he says. “One of the biggest pluses of the Dalton experience is the community — the parent community, the faculty community, the staff community, and the student community. It’s a phenomenal collection of humanity that we have here.”


In the Senior Leadership class Xiomara Hall (P9 I) teaches at The Chapin School, she stresses to her students the importance of asking for what you need and going after what you want. When the Associate Head of School position at the school opened up earlier this year, Xiomara knew the opportunity was the ideal next step in her career. But as Chapin’s Director of Enrollment Management at the time, she was concerned about the level of vulnerability that would come with being an internal candidate. As she contemplated whether to apply for the position, she reflected on the guidance she had given her students, thinking, “How am I giving that advice if I’m not following it?”

In April 2022, after a rigorous four-step employee search process, Xiomara was appointed Chapin’s next Associate Head of School. “It’s a huge responsibility and it’s a huge honor to be in this position,” says Xiomara. “I am the first person of color to get to this level on the Chapin leadership team in the school’s history.”

Two decades ago, recognizing a desire and making the decision to pursue it opened the door to a full-time career as an educator. As an undergrad at Hobart and William Smith Colleges, Xiomara took a few education classes, but didn’t view teaching as a professional goal. In the early 2000s, as a full-time student at New York Law School, working part-time as a pre-K teacher at The Episcopal School in the City of New York was initially just a way to pay the bills.

When terrorists attacked the World Trade Center in 2001, lower Manhattan — including New York Law School — shut down. Without classes to attend, Xiomara had time to think about what she really wanted professionally. “I fell in love with the intrigue, the curiosity, the openness of four and five year olds,” says Xiomara. “There was nothing in my adult life that I had done that felt as good as being in
a classroom. I made the brave decision to ignore external pressures and leave law school to devote myself to the learning process of young children.”

Xiomara spent nine years at The Episcopal School, soaking in the wonder of her young students. In many ways, they reminded her of her younger self. As a student at The Lawrenceville School, she was eager to take in all that the school had to offer. Freshman year she signed up for so many clubs that her housemaster had to put her in a school club time out so that her extracurricular activities didn’t negatively impact her schoolwork.

Xiomara has applied this enthusiasm throughout her career. A love of storytelling led her to take on admissions roles at several independent schools. Each position provided opportunities and mentorship that have helped her develop into a senior leader committed to serving her community. During her time as Director of Financial Aid and Associate Director of Admission at George School, she also served as a dorm parent, which allowed her to offer students the same type of support she received during her time at Lawrenceville. At St. Patrick’s Episcopal Day School, she found a mentor in thenHead of School Peter Barrett, who saw her potential to become a head of a school one day and supported her growth through professional development and leadership opportunities. These experiences complemented Xiomara’s previous pursuit of an intensive one-year master’s program in educational leadership and administration at the Klingenstein Center at Teachers College, Columbia University.

Now as Associate Head of School at Chapin, Xiomara is focused on bringing the school community together. “After two-and-a-half tumultuous years of the pandemic where we were deliberately siloed, an important aspect of my role this year is looking at the opportunities where K-to-12 ties can be strengthened both in and outside the classroom.”

In her day-to-day work, Xiomara draws on her time in Prep for Prep. “When I reflect back on my Prep experience I learned that I can belong in and add value to spaces that may not have initially been designed for me.” Through her work at Chapin, as a member of the NYSAIS Diversity Committee, and as a DEI workshop presenter, she wants her colleagues and students to have the same feeling.

Throughout her career, Xiomara has launched programs and initiatives to facilitate inclusion and belonging for others. She knows how instrumental this is to the formation of identity for both young people and adults. “I was able to benefit from a sense of belonging because of the guidance and support of the school leaders in my life when I was a student and an adult,” says Xiomara. “I feel honored to create spaces where others feel the same way.”


Standing in the foyer of George Jackson Academy, Ramón Javier (XI) greets middle schoolers by name as they buzz by between classes. He’s just a few months into his new role as Head of School and he already knows the name of each of the 91 boys. This effort to create a personal connection with his students was inspired by his own student experience. While walking down 91st Street to Preparatory Component at Trinity School one day, Prep for Prep’s founder Gary Simon greeted him by name. “There were 150 of us,” recalls Ramón. “I was so impressed that he knew who I was. That feeling has stuck with me to this day.”

Throughout his 20-plus-year career in education, Ramón has worked to create a similar feeling of importance and belonging for his students. As a first generation Afro-Latino, attending The Hackley School exposed him to a world quite different from what he was accustomed to in his Washington Heights neighborhood. Having a foundation of value and confidence, instilled by Prep advisors and staff, was critical to his development as a student and as an adolescent.

From Hackley, Ramón enrolled in Williams College, where he majored in political science and planned to pursue a career in law. “My mother’s an immigrant; my grandma’s an immigrant,” says Ramón. “For all that schooling, all of that extra work, for them to be able to say ‘He’s a lawyer,’ that felt like a duty I had to give them.” After graduating from college, Ramón took a job at a law firm and eventually enrolled at Manhattan’s Benjamin Cardozo School of Law. His first day of class was September 4, 2001. Seven days later, he watched the Twin Towers fall. “I knew at that moment I didn’t want to be a lawyer.”

This realization created an opportunity for Ramón to identify his true professional passions — psychology and education. He joined the staff of Prep for Prep, where he had worked as an advisor during college, in the admissions office and then as Gary Simon’s special assistant. It was there that he solidified his interest in supporting students. Says Ramón, “I wanted to be able to help address that loneliness that can happen for kids of color in a predominantly white institution.”

Ramón enrolled part-time in a master’s program in psychological counseling at Teachers College, Columbia University while working at Prep and then at The TEAK Fellowship. He expanded his ability to impact the student experience by serving as Director of Diversity, Equity, and Inclusion, first at The Packer Collegiate Institute and then at Trinity.

In 2020, the Covid-19 pandemic and racial uprising following the murder of George Floyd presented another opportunity for Ramón to assess his career direction. “I started to think about leadership in different ways,” he says. Seeing Prep alum such as José De Jesus (IX), Head of School at The Dalton School, and Priscilla Morales (XII), Associate Head of School at The Park School, step into senior leadership roles allowed him to see that as a possibility for himself.

In his first year at George Jackson Academy (GJA), Ramón is focused on “learning the culture so that I can go out and tell the story of our school in a meaningful and authentic way.” GJA is unique in the New York City independent school space. The middle school, located in New York City’s East Village, was founded in 2003 in honor of former Motown CEO George Jackson. Grounded in Lasallian principles, it serves academically gifted sixth-, seventh- and eighth-grade boys, primarily students of color from low-income backgrounds.

The school’s nurturing environment is akin to what Ramón experienced in Prep for Prep. “We were part of something important and that meant that we had a responsibility and a duty to carry that on, not just for ourselves, but for the folks coming behind us,” he says. “I felt a similar sense from the boys [at GJA] when I met them.”

Ramón’s career trajectory has proven that medicine and law are not the only pathways to success. He has contributed to creating a more inclusive environment for Prep for Prep students, and all students of color, who have followed in his footsteps as independent school students. And he has made his family proud. “When I talk to my mother about my work, and I explain what the responsibility is and what it is that I do, she is really proud of me,” says Ramón, “and she’s happy that I’m happy.”

This article appeared in the 2022 Prep for Prep Annual Report. Visit www.prepforprep.org/2022annualreport to read the full publication.
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