Leadership in Philadelphia

Meet Our Executive Leadership Team

Darryl Bundrige
Senior Vice President and Executive Director

Darryl Bundrige is the Senior Vice President and Executive Director of City Year Philadelphia. He began his career with City Year Philadelphia in 2009 as Managing Director of Impact and assumed his current role in 2015. As Executive Director, Darryl maintains strategic relationships with the School District of Philadelphia, City Year Philadelphia’s site board, corporate and philanthropic partners, and the wider Philadelphia community.

Darryl graduated from Pennsylvania State University with a Bachelor’s degree in journalism and a minor in business. A native of Pittsburgh, Darryl moved to Philadelphia to enthusiastically serve with the National School and Community Corps during the 1997-98 and 1998-99 school years, where he mentored and tutored elementary school students. Prior to joining the City Year staff, Darryl worked as Dean of Students for Belmont Charter School and Director of After-School Programs at the Center for After-School and Community Education at Foundations Inc.

Since becoming Executive Director of City Year Philadelphia, Darryl has increased public and private funding, expanded the staff from 35 to 50 employees, and reached an operating budget of $10 million, up from $8 million. Each day, he inspires, challenges and supports staff along with diverse teams of AmeriCorps members, ages 18-25, who serve as mentors and tutors in schools across Philadelphia. He has also led the execution of City Year’s Whole School Whole Child school-based service model, and launched the first ever School District Leadership Summit—an opportunity for local education leaders to meet and discuss impact.

For Darryl, service is a lifestyle. He remains a steady advocate for mentorship and youth education both at work and outside of the office. Among his many civic engagement activities, Darryl has served on Penn State’s Alumni Council, is the former co-chair of the National Service Task Force in Philadelphia, a current member of the Cedar Park Neighbor Association Scholarship Committee, and member of the Fast Start mentoring program. Likewise, he is active in the Philadelphia African-American Leadership Development Forum sponsored by the Urban League, of which he was an inaugural member.

Throughout all his roles, Darryl takes pride in connecting people to build networks and get things done. He has received numerous accolades for his work, including being named 2010 Outstanding Alumni Council Member awardee, 2015 Brothers Network honoree, the K. David Weidner Diversity Award recipient, a 2018 “Made Man” honoree, and a 2019 Philadelphia Business Journal Minority Business Leader award recipient.

Kyle Casey
Managing Director, Development

Kyle Casey began her career with City Year Philadelphia in 2008, serving as an AmeriCorps member at Olney High School. As Managing Director of Development, Kyle builds and maintains strategic relationships with corporate, foundation and individual donors to ensure City Year Philadelphia has the funding and resources needed to implement its service model with fidelity.

After Kyle’s first service year, she served as Team Leader at Feltonville School of Arts and Sciences Middle School with the Diplomas Now project. She first joined the City Year Philadelphia staff in September 2010 as Special Projects Assistant to the Managing Directors. She would go on to join the Development Department as a Development Associate and then move up in the department from Development Manager, Individual Giving Manager, Individual Giving Director, then to Senior Director of Individual Giving. A few of Kyle’s achievements include launching the Red Jacket Society major gifts program, establishing a robust individual giving program, raising almost $2 million through individual giving activities, and creating the infrastructure for City Year Philadelphia’s Women’s Leadership Luncheon, Associate Board of young professionals, and event committees. Thanks to Kyle, Philadelphia was the first site to obtain the Edgerley Family National Challenge by generating $800,000 in new, multi-year major gift commitments.

Kyle received her Bachelor of Arts degree in Business Administration from Muhlenberg College. She is also a City Year LEAD program graduate. Kyle is proud to represent the City Year alumni community as a member of the Executive Leadership team, and deeply believes in the power and impact of having City Year AmeriCorps members serving in Philadelphia schools.

Dana DiNatale
Managing Director, People and Operations

Dana DiNatale began her career with City Year Philadelphia in 2011, serving as an AmeriCorps member at Benjamin Franklin Elementary School. She returned to serve for a second year as Team Leader at Frederick Douglass Elementary School. As Managing Director of People and Operations, Dana maximizes alignment of the site’s human, financial and physical capital to ensure City Year Philadelphia provides operational excellence to its staff, AmeriCorps members and school communities.

Prior to joining staff at City Year Philadelphia, Dana served as founding Operations Manager at Young Scholars Kenderton Charter School, managing all non-instructional operations, including maintaining the school’s student data and financial systems. Dana joined City Year Philadelphia in May 2015 as Finance and Operations Manager in the People and Operations Department. She would go on to serve in a range of escalating leadership roles in the department.

Dana received her Bachelor of Science in Biology and International Relations from Syracuse University and her Master of Public Administration from Syracuse University, Maxwell School of Citizenship and Public Affairs. Dana’s passion for Philadelphia students and school communities is fueled by the City Year value “service to a cause greater than self” and the belief that regardless of background or circumstance, all youth should have access to quality education.

Dawn McCray
Managing Director, Impact

Dawn McCray is a passionate, mission driven youth advocate who has been serving youth and families throughout the five-county region for 26 years. Dawn joined City Year Philadelphia in February 2019, serving in the capacity of Managing Director, Impact. In this role, Dawn leads the development, implementation and strategy to formulate and actualize the overall vision for the Impact Department. Dawn provides oversight for more than thirty staff members. The Impact Department is responsible for deepened AmeriCorps member impact, experience and Whole School Whole Child services.

In her capacity of service as President & CEO at Communities In Schools of Philadelphia, Dawn provided fiscal, programmatic and strategic leadership for initiatives serving over 10,000 young people yearly. Throughout her 17-year career at CIS of Philadelphia, Dawn remained committed to developing her staff and serving young people through excellent service delivery in the areas of Out of School Time, Pregnant & Parenting, Aging Out of Foster Care and Apprenticeship programs. Her portfolio also included Career & Technical Education, Alternative Education, Workforce Development training and an AmeriCorps Information Technology Pre-Apprentice program. Prior to joining CIS of Philadelphia in 2001, Dawn served as Site Director for Girls and Boys Town of Philadelphia and directed oversight of more than 50 staff members. During her six-year tenure with Girls and Boys Town, Dawn’s career led her from the organization’s Greater Washington, DC, affiliate back to her hometown of Philadelphia, PA.