CCDS Names Stephen Jackson as Next Director of College Counseling 

We are pleased to announce the appointment of Stephen Jackson as our next director of college counseling. Stephen will assume the role in July 2026, succeeding Sarah Beyreis following her retirement at the conclusion of this school year after more than two decades of outstanding service to the Country Day community.  
 
“I am excited to join the Country Day community, where college counseling is rooted in authentic relationships and a shared commitment to the full arc of a student’s independent school journey,” says Stephen. “It is a privilege to support students and families through such an important and transformative chapter of growth and discovery.” 
 
Stephen brings more than 25 years of experience in independent school education, including extensive leadership in college counseling, teaching, coaching, admissions, and senior administration. He currently serves as the director of college counseling at Woodberry Forest School in Virginia, where he leads the team that guides boarding school students through the college application process. In addition to his work with students and families, he sits on Woodberry’s Executive Leadership Team, contributing to strategic planning and institutional initiatives across academics and student life. 
 
Prior to his current role, Stephen directed the College Counseling Office at Baylor School in Tennessee for a decade, where he led a team of four counselors and helped shape a comprehensive, student-centered college advising curriculum. 
 
“Stephen’s philosophy aligns beautifully with the work we do every day in the Upper School,” says Head of Upper School Jon Zeljo. “Individualized college counseling is one of the most important components of the Upper School experience. I am excited for our students and families to benefit from his steady guidance, thoughtful partnership with our faculty and staff, and belief in finding the right fit for each student.” 
 
He has counseled hundreds of students, built strong partnerships with colleges and universities nationwide, and maintained active involvement in professional organizations, including NACAC and ACCIS. Throughout his career, Stephen has remained grounded in a philosophy that prioritizes belonging, intellectual rigor, and the developmental arc of adolescence.  
 
“The best schools are not merely places of learning but communities of belonging and joy,” says Stephen. “I am especially drawn to Country Day’s willingness to expand learning beyond its campus and to encourage students to be courageous global citizens who see genius in each of us.” 
 
His individually tailored approach to college counseling encourages students to seek institutions that fit with their individual strengths, values, and aspirations. 
 
“It has been through deliberate practice that I have been able to provide appropriate options for a student when they are unaware of the university opportunities that exist beyond their immediate purview,” says Stephen. “Building a student's trust is paramount when shaping their journey.” 
 
Stephen began his career in higher education as an assistant director of admissions at the University of the South, his alma mater. Stephen received his master’s degree in teaching from Brown University and has taught English at multiple independent schools. He has also served in a variety of roles – from dorm head to tennis coach – which is reflective of his commitment to being involved in the full life of his students. 
 
Head of School Rob Zimmerman `98 expressed confidence in Stephen’s leadership and vision for Country Day’s next chapter.  
 
“Stephen brings a valuable combination of strategic leadership and deep experience. His commitment to student-centered, relationship-focused counseling aligns perfectly with the values that have long defined Country Day. As we build on the strong foundation established under Sarah’s leadership, I have no doubt that Stephen will lead a program committed to ensuring that every student finds success in college and life. We are thrilled to welcome him to our community and look forward to the thoughtful leadership he will bring to our College Counseling Office.” 
 
Please join us in welcoming Stephen and his family to Cincinnati Country Day School as we begin this exciting new chapter for our college counseling program.