James E. Rainey Jr. joined the Randolph community in the summer of 2014, to serve as the ninth Head of School in Randolph’s 55-year history.
Rainey’s appointment was the culmination of a nationwide search in which he emerged as the candidate with the values and experience to guide the School in the next phase of its growth and development as an excellent independent school. “When we heard Jay eloquently describe his philosophy for 21st century education, we realized that we had our man,” said Board Chair and member of the Search Committee Matt Fowler ’83.

A highly principled educational leader with great vision and a keen intellect, Rainey is known for his ability to forge deep and meaningful connections with students, faculty, parents and school leaders, as well as with the broader community. Rainey joined Randolph from Norfolk Academy, in Virginia, where he had served since 2002 and was most recently the Assistant Head for Academic Affairs.

Rainey holds degrees from Princeton University (A.B., Religion) and the College of William and Mary (M.A., American Studies). Prior to Norfolk Academy, Rainey spent several years in Chicago and Richmond, where he founded and directed businesses providing educational software and services for educators and students. This entrepreneurial experience provided Rainey with unique perspectives and opportunities to understand the needs of 21st century students.

“Great schools are deeply and authentically connected to their cities,” says Rainey. “A great school should invest in local assets and relationships, both within and beyond the schoolhouse, while at the same time taking advantage of the ‘technologies of ubiquity’ (e.g., cloud computing, flipped instruction, distance learning) on behalf of its students. The former shape the character, our understanding of which is timeless and grounded; the latter shape the mind, our understanding of which is ever expanding and untethered. Each is essential to the education of a child, and I believe that Randolph is well positioned to continue its work on both fronts.”

Randolph’s “growth mindset” was very appealing to Rainey during the Head of School search. “The School has grown, and continues to grow, not merely in terms of enrollment or even program offerings, but more substantially in terms of its aspirations to enrich and advance the lives of the students it serves, and its willingness to 'stretch' and challenge long-standing assumptions and practices, such as the daily schedule and the use of instructional technologies, toward the realization of those aspirations. Randolph is a forward-looking school in a forward-looking city, and I cannot imagine a more exhilarating story to be a part of as an educator, nor a better opportunity for Ruth and me to provide to Jed and Elizabeth as they grow into adulthood."

Jay and Ruth, native Virginians, have two children, Jed ’20 and Elizabeth ’22.