Board chairs from three classical Christian schools in different geographies with different challenges and opportunities will talk about how their boards are being flexible in the face of unexpected upheavals while still keeping a disciplined eye on their schools’ long term strategic goals. They will discuss how they’ve given their heads of school support and where they’ve drawn the line between their work and their Heads’. Attend, listen, and bring your real world questions.

John A. Riley

John A. Riley founded Legacy Fund in 2006 for the purpose of investing in privately held businesses and commercial real estate. Prior to Legacy Fund, Mr. Riley was Co-Founder of PlanSource in 1997. PlanSource is a technology company providing flexible and intuitive software and services for benefits administration to over 4.5 million consumers in the US. Under the PlanSource umbrella, the company also founded and operated CoAdvantage and ZeroChaos. CoAdvantage, one of the largest Professional Employer Organizations in the United States, services over 4500 clients and 90,000 worksite employees. ZeroChaos, with annual revenues exceeding 3.8 billion dollars, pioneered a new staffing model changing the way Fortune 200 companies source, manage and administer their contract labor workforce. PlanSource was sold in 2019.
He serves on several boards of private and non-profit organizations including Rollins Crummer Center for Advanced Entrpreneurship, ABC Fine Wine & Spirits, Edyth Bush Charitable Foundation, Sighthound, Alterna Capital Solutions and The Geneva School.
Mr. Riley received his bachelor's degree in liberal arts from Rollins College in 1982 and a bachelor's degree in chemical engineering from Georgia Tech in 1984. He lives in Winter Park with his wife of 30 years and has two daughters.