Mr. Williamson’s Road to Windward

Stephanie Huie

Windward Welcomes Jamie Williamson as Head of School 

When you step into Jamie Williamson’s office at the Westchester Middle School campus, you get a brief glimpse into who he is—a proud father and husband, avid reader, cycling enthusiast, and a creative thinker. There are smiling photos of Mr. Williamson’s family on his desk and framed pieces of his children’s artwork hanging on the walls. Scanning his bookshelf, you see titles spanning varied genres and disciplines, from Daniel Pink’s Drive about the research of motivation to Simon Sinek’s Leaders Eat Last on fostering an environment of trust. A large, poster-sized print detailing the evolution of bicycle styles sits prominently near his desk, indicating one of his great personal interests. A colorful art deco illustration of the Cincinnati riverfront serves as a sentimental reminder of Mr. Williamson’s midwestern roots and the beginning of his career.  

The personal mementos decorating his office certainly begin to offer some insight into the person who occupies the space, but, when weaved together with the understanding of the values instilled in him during his upbringing, his undergraduate and graduate education, his extensive experience working in schools, and his unmistakable, mission-driven attitude to serve the needs of children, only then does Mr. Williamson’s character crystallize. Mr. Williamson is a leader in the field of education whose heart and bottom-line focus is on being a fierce advocate for children with learning disabilities.  

Beginning his tenure as head of school on July 1, 2019, Mr. Williamson is swiftly integrating into the community and has pushed forward in continuing Windward’s mission of providing the best educational program for the remediation of language-based learning disabilities. Only halfway through his first year, Mr. Williamson will continue to make his mark in delivering upon these ambitious aims and shape his vision of the Windward Way at what is just the beginning of his journey at The Windward School. 

Growing Up with Appalachian Family Values 

Jamie Williamson grew up with his parents and younger brother in a rural coalfield community in the Appalachia region of eastern Kentucky, near the Virginia and West Virginia borders, thirty minutes away from the closest town, Pikeville. His extended family had lived in the community for generations, so the Appalachian culture of connectedness, family, hard work, and putting in one’s best effort was ingrained into him at a young age. Mr. Williamson’s father was an auto diesel mechanic and worked for a coal mining company for most of his career. Other members of the family were similarly in blue-collar jobs as miners, railroad workers, and electricians. “When I was growing up, I remember both my dad and mom having absolutely incredible work ethics,” said Mr. Williamson. “My parents and grandparents taught me to always do my best and put in a good effort, so I’ve never been afraid of a hard day’s work, physically or mentally.” 

Compared to growing up in a metropolitan area of a suburban neighborhood, Mr. Williamson’s childhood community was isolated, so access to educational opportunities proved to be a challenge. To satisfy his natural curiosity about the world around him, Mr. Williamson took it upon himself to read constantly. “In the environment that I grew up in, I couldn’t learn things haphazardly; I had to do my own digging by reading every book I could find,” recalled Mr. Williamson. “From a young age, I had a hunger to understand different perspectives, which was born out of the fact that I didn’t have much exposure to the world, but I wanted it. I always wanted to know more than I did yesterday. I’m proud to be where I’m from, in the hills of Kentucky, as it taught me this great work ethic of perseverance and tenacity.”  

And although Mr. Williamson considers his dad to be one of the best problem-solvers and his mother a voracious reader, his parents did not have the opportunity to go to college themselves. Their lack of educational options motivated them to ensure that Mr. Williamson was able to move further ahead in his education. With great pride and determination, Mr. Williamson was the first person in his immediate family to go to college. 

Searching for Purpose and Autonomy in Psychological Work

Upon arriving at Western Kentucky University, Mr. Williamson did not have a clear vision for what his future might hold—that is, until his sophomore year. “I took a psychology class with Professor Dan Rocker that showed me how insights could be gained through statistical research,” recalled Mr. Williamson. “The process of formulating a research question was extremely interesting to me, and, at the end of the semester, Professor Rocker said he hoped we could be colleagues one day. I never had anyone take an interest in me like that, and it lit a fire in me.” Mr. Williamson probed deeper into his burgeoning interest in experimental psychology by enrolling in more classes to become well-versed in research methods and psychological assessment. He also worked in a gerontological cognitive lab, examining executive functioning and frontal lobe functioning in older adults, and he became enamored with the brain-based focus of the research. Through psychology, Mr. Williamson found an area of interest that blended purposeful work with problem-solving. 

Post-college, Mr. Williamson took his first role as a research study coordinator at a veteran’s hospital for a medication trial for healing crack cocaine addiction for the U.S. Food & Drug Administration. He loved working with study participants, which lead him to the realization that he would rather spend more of his time interacting directly with people. Instead of focusing solely on research, Mr. Williamson desired to have a bigger impact on the lives of others, particularly children. So, he switched to serving as a caseworker for some of the most complex children in Cincinnati, with clients in the delinquency and dependency court system. In this role, Mr. Williamson frequently interacted with the administrators and psychologists of the children’s respective schools. He quickly became frustrated with the systemic indifference towards the children he worked with, many of whom struggled with learning disabilities or foster home instability.  

Mr. Williamson once again reconsidered how he could best make a positive impact on the lives of as many children as possible, and he decided to refocus on school psychology. He earned a master’s and an educational specialist degree from Miami University of Ohio before working as a school psychologist at a public middle school for the next four years. During that same period, Mr. Williamson also received an educational leadership and administration license from Xavier University.  

In the Cincinnati public-school system, Mr. Williamson became known as an impassioned advocate for dyslexics. He initiated conversations about early intervention to teach fundamental reading skills rather than being overly preoccupied with earning high marks on the end-of-year state achievement tests. Above all else, Mr. Williamson valued meeting every child’s needs, especially those with learning disabilities, so he began contemplating whether working in independent schools might be a better fit for him. 

“The Work Found Me”: Shifting to Educational Leadership

Then one day a friend called Mr. Williamson to ask for his advice. His friend was planning to apply for an open position for principal at Springer School and Center, an independent school for students with learning disabilities, and he wanted to draw upon Mr. Williamson’s experience to give him a general overview of the educational landscape concerning learning disabilities. After chatting about the position, his friend eventually said to Mr. Williamson, “Why don’t you apply for this job?”  

A moment of realization hit for Mr. Williamson, as he had always been a systems-level thinker that sought ways to impact more children; this track to becoming a school administrator could be precisely what he had been searching for in his career. Mr. Williamson’s credentials and educational philosophy fit perfectly for a leader of a special needs school, and he “loved every minute” of his next seven years at Springer. During his tenure, Mr. Williamson’s reputation as an effective leader grew, and Marburn Academy, another independent school for students with learning disabilities, recruited him to become their next head of school. Mr. Williamson and his family relocated two hours northeast to settle in Columbus, Ohio, where he followed a 27-year veteran and successfully lead Marburn through a major growth phase over the course of four years.  

“The work found me,” said Mr. Williamson. “I wasn’t seeking leadership opportunities when I discovered the principal position at Springer. Then Marburn called and then Windward called. At every juncture, I evaluated what good systems-level organizational thinking could I bring to this community, and how could I contribute to building something bigger to support more children? At every step of this process, I’m always drawing a line back to the mission and children. As a leader at these educational institutions, I’ve had an opportunity to make a positive impact on the world and support this important work to the best of my ability. 

“What I love about this position is the ability to so positively change the trajectory of a child’s life by teaching them how to read. Our school serves such an important mission. If we didn’t exist, our students would suffer. I know families make a sacrifice to be here—financially, logistically, emotionally—and I feel a huge responsibility to deliver on our promise to take care of our students. As a head of school, I want to make sure the children find joy in learning to read, feel valued, and feel seen.” 

The Beginning of the Road at Windward 

Why Windward? What about Windward made Mr. Williamson realize that this was the school for him? 

“The Windward School’s reading and writing programs are second to none. The commitment to teacher training is unparalleled, and the teachers that reap the rewards of the countless hours of professional development are incredible.”  

“My two core values are growth and impact, and The Windward School’s educational philosophy aligns with mine. We understand what our students need, we follow the research on how to best serve them, and we are always striving to be better. The children are the center of all decisions at Windward, not state policies. Everyone in The Windward School community cares about the whole child, from their experiences before they walk in the door to when they leave for their next school. Windward’s impact on the world is expanding, and I’m incredibly proud to contribute to its work remediating children with language-based learning disabilities.” 

In his first six months as head of school, Mr. Williamson has certainly been contributing to Windward’s endeavors in its research-based partnerships, outreach programs, and ensuring the best educational program for its students. In collaboration with The Windward Institute, the Windward/Haskins Laboratories Collaborative Project has reached the milestones of training Windward faculty to assist in the newly installed EEG labs and beginning the Predicting Literacy Outcomes at The Windward School in-school research study. Mr. Williamson has welcomed international visitors interested in learning about Windward’s curriculum, including Mrs. Brigitte Macron, First Lady of France. This school year also marked a record-high enrollment of 936 students across Windward’s three campuses, an increase of 22 students from last year, including the inaugural class of first-grade students at the Manhattan Lower School. 

Mr. Williamson has also been present at countless school events, and he is frequently accompanied by his family. Mr. Williamson and his wife, Krista, have been married for more than 15 years. Their children are Isaac, a ninth grader, and Etta, a fifth grader. The family also has a beloved dog, Rosa. Over the summer, the Williamsons had a successful move from Ohio, and they settled smoothly into their new home in Irvington. The family has been enjoying exploring the Hudson River towns as well as trips into the city to see Broadway performances and visit art museums. 

The support that Mr. Williamson and his family have received from the Windward community during their first year has been "immense and sincerely appreciated,” and Mr. Williamson has been returning that same degree of warmth as he continues to get to know the entire Windward community—faculty and staff members; parents and guardians; students; alumni; and alumni parents/guardians. The calendar for the second half of the school year is filled with many festivities that Mr. Williamson looks forward to experiencing with the Windward community, including the Winter Ice Skating Party at Bryant Park; each campus’s drama performances; winter and spring athletic games; WPA’s CommUNITY Service Day; the Robert J. Schwartz Spring Lecture; Spirit Week; WPA’s Dream Big; Field Day; lower-school spring concerts; moving-up ceremonies; and graduation and recognition ceremonies. As strategic milestone projects also loom ahead, such as the construction of the new Westchester Lower School campus, Mr. Williamson trusts that he, along with the board of trustees and school administrators, will help lead The Windward School into a robust and promising next chapter. Although the road ahead for Mr. Williamson will be full of great challenges and opportunities, his passion for his work and his purpose-driven approach will steer The Windward School closer to achieving its vision: a world where every child with a language-based learning disability is empowered to achieve unlimited success. DIFFERENCE IS POWER.