Ruth is a passionate education and nonprofit leader. Prior to joining Prep for Prep as CEO in July 2020, Ruth was Associate Principal at Francis W. Parker School in Chicago, overseeing educational programs and operations, and before that, High School Principal at LREI (Little Red School House and Elisabeth Irwin High School), an independent, progressive school in New York City’s Greenwich Village.
Ruth earned her undergraduate degree in English Literature from Connecticut College and has a master's degree in English and American Literature from Brown University. She founded the Administrators of Color in Independent Schools Conference and serves as a trustee on the boards of the Brooklyn Museum, Moorestown Friends School, LREI, Kura Labs (a nonprofit that offers free training and a job placement academy for students from underserved communities interested in Infrastructure Computing, DevOps, and Site Reliability Engineering), and The Dovetail Project (a nonprofit that helps young African-American and Hispanic men with fatherhood).
Sharon Madison joined Prep in 2015. She came to us from the Federation of Protestant Welfare Agencies where as Chief Operating Officer she oversaw the $50-million sale of the Federation's landmark building and staff's relocation to new headquarters while also overseeing finance, facilities, IT, and human resources. Prior to the Federation, Sharon held several executive roles at Sports & Arts in Schools Foundation including Director of Administration, Director of Development, and Business Director. Her corporate experience includes marketing and account management work at Saatchi & Saatchi, Time Warner, and Verizon as well as serving as the COO/CFO who helped to turn around a unionized commercial cleaning company with Fortune 100 clients. A native New Yorker, Sharon is a graduate of Hamilton College where she serves as a Charter Trustee. She has also served for more than a dozen years on the Board of the Children's Aid Society.
A member of Prep's Contingent XII, Jackson Collins, Ed.D., served as Prep's Director of Counseling before assuming his current role as Executive Director. He came to us from The Shipley School in Bryn Mawr, Pennsylvania, where he most recently served as the Upper School Dean of Students and Associate Head of the Upper School. A member of the Upper School Admission Committee, Jackson also chaired the Upper School History Department. Prior to Shipley, he worked at The Episcopal Academy where he served as Upper School Form Dean, history teacher, and basketball coach. Jackson began his professional independent school career at his alma mater, Saint Ann's School in Brooklyn, where he was the Coordinator of Interscholastic Athletics.
Jackson graduated from Amherst College and earned a Masters in Education Leadership from the Klingenstein Center at Teachers College Columbia University and an Ed.D. in Education Leadership from the University of Pennsylvania. Jackson serves on the Board of Managers for the Oakwood Friends School and on the Board of Directors of LEADERSHIP Philadelphia. He also founded and operates Nine Nickels, a nonprofit organization inspired by his grandmother to promote socioeconomic progress through education and opportunity.
Director of Development and Strategic Partnerships
Rebecca Ervey first joined Prep for Prep in 2006 and now has the role of Director of Development and Strategic Partnerships, where she oversees fundraising and designs partnerships with mission aligned organizations. Previously, she served as Prep’s Director of Professional Advancement where she led the development of over 4,500 paid internships with several hundred companies in close collaboration with Prep’s Alumni, Board of Trustees, and Associates Council. Rebecca’s prior experiences include serving as Senior Director of Strategic Initiatives for Leadership Enterprise for a Diverse America (LEDA), where she raised funds and built partnerships to launch their career and alumni programming, and managing technology programs across CUNY schools, where she developed internships with early stage start-ups and helped build a tech incubator. She also spent years in Seattle, Washington, where she focused on workforce development initiatives including managing federal and state grant programming at the community college level. Rebecca is a graduate of New York University and lives in Brooklyn with her husband and two children. She volunteers as class parent and serves on the IAC Foundation Scholarship Committee.
As the Director of Post-Placement Counseling, Roberta Osorio oversees the department that supports Prep for Prep students once they have enrolled in their respective independent schools. She brings two decades of academic and administrative experience to the role. Before joining Prep she served as Middle School Academic Dean at the Convent of the Sacred Heart. She has also held positions at Ethical Culture Fieldston School, Worcester Academy, the Swift School, The Galloway School, and Nobles and Greenough School.
Roberta has a bachelor’s degree in English Language and Literature/Letters from Columbia University and a Master of Education from Harvard Graduate School of Education. In addition to her full-time position, she volunteers as the Co-Director of the New York City chapter of People of Color in Independent Schools, an affinity support and networking group for staff, faculty, and administrators of color.
Roberta is married to a Prep alum, Eric Osorio (VIII), and is a former Preparatory Component faculty member.
Cindy has been developing close relationships with Prep students, independent school partners, college personnel, and colleagues for over two decades. She originally joined Prep in 2000 as an Undergraduate Affairs Officer before transitioning to the role of College Counselor four years later. When she left to obtain her master’s degree, Cindy returned during the summers to teach Psychology in the PREP 9 Preparatory Component. After serving as Executive Coordinator for George Washington University’s study abroad programs, she returned to Prep in 2010 as Director of College Guidance and in 2018 joined the executive leadership team as Director of Leadership Development Opportunities. Cindy has also taught and served as an academic advisor at CUNY's Guttman Community College.
Cindy is a graduate of Hamilton College, where she is a member of its Alumni Council and serves as Vice Chair for the Committee of Equity and Inclusion. She holds a Master’s Degree in Higher Education Administration from George Washington University and a certificate in Human Resources Fundamentals from Baruch College.
As Prep for Prep’s Director of Admissions, Johanna oversees the recruitment, testing, and admissions process for nearly 4,000 annual inquiries for the program. Johanna came to us from New York’s Poly Prep Country Day School where she was Director of Enrollment Management and Financial Aid. A Brooklyn native, Johanna is an alumna of Poly, which currently enrolls over 40 Prep students. Having returned to the school in 2009 to work full time, Johanna held positions of increasing responsibility in the Admissions Office focusing on the middle and upper schools. In addition to serving on Poly's Administrative Council, she coached JV Softball and co-taught Senior Leadership, a senior elective class which a number of Prep students have taken over the years. Johanna earned her undergraduate degree from Williams College, where she led the Varsity Softball team.
Nikole Smith became the Director of the Prep for Prep Preparatory Component in 2004. Prior to joining Prep for Prep on a full-time basis, she served as Dean of the junior class and Diversity Coordinator at Poly Prep Country Day School, where she was a member of the history department for eight years and coached championship volleyball teams. Her association with Prep for Prep began in 1989 when, as a student at St. Andrew's School, she became acquainted with PREP 9 students. From 1989 to 2004, she served as a PREP 9 advisor, chaperoned college trips, and taught both Prep and PREP 9 students. In July 2014, Niki assumed her current role of Director of Academic Programs and now oversees both the Prep for Prep and PREP 9 Preparatory Components. Nikole holds a BA in Psychology, Education, and African American Studies from Mount Holyoke College and has completed work towards her MA in Sociology and Urban Education from Columbia Teacher’s College.
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LEADERSHIP PROGRAMS & ADMINISTRATION 328 West 71st Street New York, NY 10023 P: 212.579.1390
We envision a nation guided by ethical and effective leaders that reflect our diverse society.
Prep for Prep's mission is to develop future leaders by creating access for young people of color to first-rate educational, leadership development and professional opportunities.