Stephen Jackson, a college counseling professional with more than 20 years of experience, has been named Woodberry Forest's new director of college counseling. Mr. Jackson comes to Woodberry from Fountain Valley School in Colorado, where he has spent this past year working as both a college counselor and a dorm head. Prior to that, he was director of college counseling at Baylor School in Tennessee for ten years. 

Mr. Jackson is a graduate of Sewanee: The University of the South, where he was a Division III All-American tennis player. Over his career, Mr. Jackson has held positions as a tennis coach, campaign press secretary, sales coordinator for Prada, and assistant director of admissions at Sewanee before moving into his first role as a college counselor at The Taft School in Connecticut. Mr. Jackson arrived at Baylor in 2006 to serve as associate director of college counseling and English teacher. In 2012, he was named director of Baylor’s college office, a position he held for 10 years. During his time at Baylor, Mr. Jackson served on four university advisory boards: Samford University, the University of Georgia, the University of South Carolina, and the University of Tennessee. 

“I love being a college counselor and helping young people navigate the college process,” said Mr. Jackson. “My time as an English teacher certainly helped sharpen my skills for working with students, but as a college counselor, I get to work with them in an entirely different capacity. It’s incredibly rewarding to be able to give to each student individual attention.”

Mr. Jackson will be moving to the Woodberry campus this summer with his wife, Barbara. The couple have three children: Lucia, who is a junior at Montana State University; Eli, who is a freshman at Wofford College; and Garrit, who is a junior at Baylor School. 

“I’ve spent most of my career working at boarding schools, and I couldn’t be more excited about moving to Woodberry,” said Mr. Jackson. “Boarding is such a wonderful experience for teenagers. In some ways, it's the purest form of a shared experience. It breaks down silos and helps students — because it's the stories and experiences we share that are indelible and invaluable.”

“I am very excited to welcome Stephen and Barbara to Woodberry Forest,” said Headmaster Byron Hulsey '86 P'22. “Over many years, Stephen has established himself as a leader in the world of college admissions. Among his many strengths, Stephen is known in particular for his ability to forge positive relationships with students at an exciting and challenging time in their lives. Most of all, Stephen and Barbara have a deep affinity for boarding schools, and they will make a lasting contribution to the Woodberry community.”

Stephen will start at Woodberry on July 1, 2024.