Executive Director, Youth Sentencing and Reentry Project

The Organization

Salary: $125,000 annually plus benefits and support for relocation

Location: Philadelphia Office (hybrid)

The Youth Sentencing & Reentry Project (YSRP) is inviting nominations and applications for the role of Executive Director.

Reporting to the Board of Directors, the Executive Director will be a visionary leader who will inspire the team, client-partners, and stakeholders to build on their current success and chart a new and exciting path forward. More specifically, they will oversee operations and serve as the senior thought-leader across all programs, including mitigation and reentry support, policy reform, and development in accordance with YSRP’s two-year strategic plan. They will also engage the sector as they maintain and build relationships that will support YSRP’s growth and goals.

The ideal candidate will be deeply committed to YSRP’s assertion that children should not be in adult jails and rely on YSRP’s values, including justice, integrity, wellness, and client-partnership to drive toward success. In fact, we are particularly interested in meeting candidates who were incarcerated as children, who spent time in adult jails, or have proximity to those who have spent time in adult jails. Additionally, the ideal candidate will also have at least 7 years’ experience managing people, leading programs, and overseeing operations in small to medium-sized organizations. Their expertise will be in reentry, juvenile justice, criminal justice policy reform, mitigation, legal defense and advocacy, or a related field. They will also have a deeply nuanced analysis of Pennsylvania’s legislative landscape with the understanding that the current criminal justice system is rooted in the legacy of chattel slavery and white supremacy.


The Youth Sentencing & Reentry Project (YSRP) is a Philadelphia-based nonprofit organization that uses direct service and policy advocacy to transform the experiences of children prosecuted in the adult criminal justice system and to ensure fair and thoughtful resentencing and reentry for individuals who were sentenced to life without parole as children (“Juvenile Lifers”).

Our Core Work includes:

  • Mitigation – During the court process in individual cases, YSRP presents prosecutors and judges with mitigation reports, or humanizing narratives of a person’s experience.
  • Reentry Planning – As close to a child’s arrest as possible, YSRP creates individualized reentry plans that connect youth with critical supports and services in housing, employment, education, and health and mental health care.
  • Juvenile Lifer Support – YSRP continues to support Juvenile Lifers who were resentenced pursuant to Miller v. Alabama and Montgomery v. Louisiana through parole assistance and reentry, including applications for clemency.
  • Training for Legal Defense and Advocacy – YSRP creates tools and provides trainings for defense attorneys, as well as trainings for law students and social work graduate students at U Penn to provide mitigation and reentry support for young people and their families.
  • Advancing Policy Reform – YSRP aspires to end the practice of charging youth in adult courts. In the interim, YSRP’s policy advocacy chips away at the harmful impacts of adult incarceration on people and their families.

Position Overview


Provide Visionary & Strategic Leadership

  • Lead YSRP with a unifying, synthesizing view of the organization’s current strengths and how those strengths can be leveraged to elevate YSRP into its next era.
  • Work collaboratively with the Board of Directors to ensure all YSRP programs and operations align with the strategic plan and support the long term growth of the organization.
  • Oversee the development of annual program plans and budgets for approval by and in collaboration with the Board.
  • Provide the Board with the information needed to responsibly exercise their fiduciary duties, govern the organization and engage in strategic decision-making, be apprised of major events at the organization on a regular basis, and serve as partners, where applicable, in fundraising, communications, and policy efforts.

Oversee Operations

  • Oversee all operations, ensuring that all programs and practices align with the strategic plan and long-term goals for YSRP.
  • Direct all hiring and personnel processes, including the creation of relevant, human-centered recruiting, onboarding, performance evaluation, and retention processes.
  • Inspire team, client-partners, and stakeholders to build on their current success across all programs by
    • Supporting the development team as they maintain current funding relationships while expanding the portfolio to introduce new funding opportunities.
    • Collaborating with the policy director to learn the nuances of the legislative landscape and work strategically to advance YSRP’s policy goals in collaboration with programs.
    • Empower the advocacy team to maintain strong relationships across the sector and continuously refine the mitigation, reentry, and legal training programs.

Curate a working culture that embodies YSRP’s values

  • Incorporate anti-racist, human-centered management practices that challenge the norms of nonprofit culture.
  • Lead with transparency by modeling interpersonal communication styles and relying on multiple modes to listen to and learn from staff, stakeholders and client-partners.
  • Use change management strategies to support the team as they grow while navigating the founder transition.

Maintain & build sector partnerships

  • Partner with the senior leadership team to connect with existing sector partners in community leadership, advocacy, policy reform, and criminal defense and reentry
  • Nurture ongoing relationship building with client-partners, relying on their lived experience to inform the work of YSRP.
  • Initiate new relationships across the sector to support the long-term growth of YSRP’s programs and development goals.


While no one person will embody all of the qualifications below, the ideal candidate will bring most of the following:

  • At least 7 years’ experience leading diverse teams, projects and/or programs in a nonprofit setting
  • Experience building alignment between mission and vision and driving buy in from different teams and stakeholders on the organization’s goals.
  • Experience maintaining team cohesion and stability during periods of transition and/or and rapid growth.
  • Lived-experience with, or proximity to, Philadelphia’s justice system and its treatment of youth.
  • Excellent written and public communication skills with experience centering multiple ways of knowing and working.
  • Demonstrated alignment with and a commitment to lead according to anti-racist theories, values and practices.
  • Experience working alongside and within criminal justice systems with a lens of working toward large-scale social and racial justice.
  • Experience managing the fiscal priorities of an organization.
  • Experience partnering across teams (development, programming, outreach, communications, etc) to align goals, timelines and priorities.
  • Experience leading or partnering on the recruitment, hiring, onboarding and evaluation of team members.


  • Demonstrated alignment with YSRP’s mission and values as a racial justice organization.
  • The ability to balance nonprofit leadership with the critical hope necessary to work within a system that continues to inflict harm upon Black, Brown, poor and disabled bodies. This means maintaining a long term vision of abolition with the short term actions needed to mitigate the harms of the current carceral system.
  • Ability to get up to speed quickly, and develop relationships with staff, Board members, funding partners, donors, consultants, and other partners and stakeholders.
  • Outstanding, demonstrated organization and critical-thinking skills; attention to detail.
  • Ability to prioritize competing projects with a range of partners.
  • Situational and organizational awareness during periods of transition.
  • Commitment to handling sensitive information with confidentiality.
  • Commitment to curating a kind, compassionate, trauma-informed, and productive working environment that respects and values diverse ways of knowing and working
  • Experience with piloting and implementing workplace innovations and technology that drive success and collaboration.
  • Please review YSRP’s list of organizational values to ensure alignment with the organization’s guiding principles


$125,000 annually. This is a full-time, exempt position. YSRP offers a comprehensive benefits package, including 100% employer-paid health and dental insurance, and retirement benefits.


YSRP has partnered with Monday Morning Consultants to lead this search. Please send questions or nominations to or  Given the nature of YSRP’s mission, Black, indigenous, and other people of color, disabled people and those who are directly impacted by incarceration – or who have a loved one who has been impacted – are strongly encouraged to apply.

To apply for the position, please submit your resume, and a brief statement responding to the following questions, to: Be sure to include the name of the role in the subject line of your email.

  1. How do your skills and background align with this job?
  2. In what ways do you prioritize racial justice and/or ending mass incarceration in your personal and professional life?
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