“Diahann Billings is the ideal leader for Prep at this moment in its history, bringing to the role a dynamic energy, and a deep personal and professional understanding of Prep’s unique role in developing ethical and effective leaders. Over the course of her career, Diahann has established an outstanding track record of advancing similar initiatives across multiple sectors and constituencies,” said Lisa Cashin, Chair of Prep’s Board of Trustees. “We look forward with great excitement to her tenure as Prep’s next CEO.” 

“I could not be more thrilled to return home to Prep—a community that enriched my own life in countless ways and helped shape the person I am today,” said Ms. Billings. “Prep set me on the course to become a results-driven, values-oriented leader, and I believe these skills will serve us well at this unique moment in time. I look forward to working with the Board, and our outstanding team of professionals, talented students and alumni, proud families, dedicated independent school partners, and our many other supporters, as we advance Prep’s vital mission and expand our impact together.” 

Ms. Billings will assume the CEO role in August 2025. At that time, Jackson Collins 
(XII/Saint Ann’s ’96, Amherst ’00) MA, Teachers College ’09, EdD, Penn ’18, who has served as Interim Chief Executive Officer since October 2024, will resume his role as Executive Director of Prep. “We are extremely grateful to Jackson for selflessly stepping up to lead Prep during this interim period,” Ms. Cashin said. “His deep knowledge of the organization as an alum and executive staff member, steady leadership, and thoughtful approach helped ensure that Prep remained on course during this transition period.” 

Prior to RISE, Ms. Billings served as Executive Director of Cultural Investments at Time Warner, Inc. and Vice President for the Time Warner Foundation. For four years she directed corporate philanthropy, led employee engagement, and oversaw the grant making and operations of the Foundation. Prior to that, New York City Mayor Michael Bloomberg appointed Ms. Billings as Chief Service Officer. In that role, she led the mayoral agency, NYC Service, and the Mayor’s efforts to help New Yorkers connect to service opportunities, target volunteers to address the city’s greatest needs, and promote service as a core part of being a New Yorker. Under her leadership, the agency engaged more than 1.3 million New Yorkers in a range of volunteer activities.  

Earlier in her career, Ms. Billings held various roles at Prep, including serving as Director of Leadership Development Opportunities from 2003 to 2005. She has received numerous recent awards and recognitions, including Crain’s Notable Women in Sports and Forbes’ Forty Women to Watch Over 40.