Inspire, illuminate, lead.

Meet Jay Rainey, our  Head of School at MICDS.

The MICDS Board of Trustees appointed Jay Rainey as Head of School in the fall of 2018. Since embracing his role in July of 2019, he has, in partnership with our Board of Trustees, overseen our 100-acre campus of 1,250 students across the Lower, Middle, and Upper Schools while supporting parents, faculty, staff, and alumni.

At MICDS, Mr. Rainey thoughtfully guided the School’s pivot to synchronous learning through the pandemic. He subsequently facilitated the return to in-person learning, all while positioning MICDS as a leading, adaptable, digitally-savvy institution with full enrollment in both pandemic and non-pandemic times. He supported the development of our now annual Arts Fest, a spring celebration of our arts students and faculty. He launched Winter Term in 2024, a two-week period between the fall and spring semesters where our students experience specialized classes, global learning trips, senior internships, and job shadowing opportunities outside of the traditional school structure. He developed the Joint Statement to Parents and Guardians on Smartphones and Social Media, which 48 schools endorsed, and he led MICDS in implementing a research-based cell phone, headphones, and social media policy in the fall of 2024. Most recently, Mr. Rainey helped create a new Strategic Plan in January 2025. 

Currently, Mr. Rainey is overseeing substantial campus projects, including the Beasley Lower School renovation and the construction of The Michael W. and Quirsis V. Riney Family Tennis Center. 

Mr. Rainey transitioned the school from trimesters to semesters and developed a more inclusive cultural and religious holiday calendar for the school. He also led the Middle School’s transition from a single-gender coordinate model to co-educational.

Beyond campus projects and overarching policies, Mr. Rainey’s equally impactful moments have been through his daily interactions with the MICDS community. He brings laughter as a mystery reader in Senior Kindergarten, a club advisor in Upper School, and he often plays piano at various concerts or Parents Association luncheons. Much to the delight of students, Mr. Rainey and his wife, Ruth, are often seen with their dog Nelson greeting MICDS Rams across campus. He dresses up for Halloween, leads silly competitions at all-school assemblies, and invites first graders to interview him, where he imparts his wisdom, stating, “Happiness is treating other people like they are the center of the world.” He’s even been spotted serving Brussels sprouts in the Middle School cafeteria.

Mr. Rainey came to MICDS from Randolph School, a K-12 independent school with 950 students, where he served as Head of School since 2014. Prior to Randolph School, he spent 12 years at Norfolk Academy, where he served as a math and English teacher, coach, and college counselor before being promoted to Director of Studies and ultimately, Assistant Head for Academic Affairs.

Mr. Rainey shares, “I am thrilled and humbled every day by the opportunity to lead a school established by the vision of William Greenleaf Eliot in 1859, advanced by previous school leaders and sustained by the dedication of faculty, administrators, and trustees today. I am committed to furthering educational opportunities for individual students in consonance with the MICDS Mission and current Strategic Plan, and I am equally committed to prioritizing a collective spirit of compassion, selflessness, and love of School during my tenure as Head of this proud and thriving School community.”

Mr. Rainey also has eight years of entrepreneurial and business experience. He earned an undergraduate degree from Princeton University and a master’s degree from the College of William & Mary. He is an avid reader and also enjoys playing piano, riding his bike, and taking walks with Ruth and Nelson. The Raineys have two children.