Evening School Principal

YouthBuild Philly • Philadelphia, PA

5d • $125,000 - $135,000

About The Position

The Evening School Principal will lead the launch, development, and long-term implementation of YouthBuild Philadelphia’s new Evening School Program, a central component of our organizational growth strategy. This leader believes deeply in the potential of opportunity youth, excels at building new systems, and is committed to fostering a warm, rigorous, community-centered school experience. From January 2026 through August 2026, the Evening School Director will focus on planning for the program launch, ensuring the program is fully enrolled, designing and leading onboarding, hiring all evening staff, and collaborating closely with the Principal/Head of School and Chief of Staff & Strategy. The primary responsibility for this role will be leadership of the evening program. However, we are seeking a leader eager to grow over time and serve our full school community, including providing seamless school-wide leadership support when the Principal is out of the building. The Evening School Director will also spend intentional time immersed in our day program prior to the launch, both to provide support, as needed, and to internalize the YouthBuild way through direct exposure to our culture, instructional systems, and leadership practices. Beginning September 2026, the Evening School Director will assume full leadership of the evening program and serve as a member of the broader school leadership team.

Requirements

• Invested in our core values - Respect, Excellence and Perseverance.
• Equity-focused and believe that all students can achieve.
• Passionate about community service and civic engagement.
• Excited to mentor students and support them throughout their time at YouthBuild and beyond.
• Collaborative and dedicated to personal and professional development.
• Demonstrated experience affecting positive organizational change and leading staff to accomplish ambitious goals in the face of challenging obstacles.
• Demonstrated values that align to restorative practices.
• A relentless work ethic, perseverance, a high degree of patience, and grit to push through challenges.
• High energy with the ability to multi-task and execute quickly.
• Strong judgment, initiative, and decision-making.
• Ability to deliver a direct and difficult message while remaining warm and supportive.
• Exceptional oral and written communication skills as demonstrated by the ability to communicate effectively and respectfully with principals, teachers, colleagues, and diverse community members.
• Excellent leadership, analytical, interpersonal and communication skills, strong customer service orientation, including expectation setting.
• The ability to influence through listening, writing, and presenting.
• A Bachelor’s degree from an accredited college or university is required (Master’s Degree strongly preferred).
• A current PA Issued Principal Certification.
• A minimum of 10 years of educational experience, 5 of which must have been in a school leadership role (current or previous experience as a principal or assistant principal, strongly preferred).

Responsibilities

• Lead the full planning process for the Evening School Program from January–June.
• Set academic, culture, and enrollment priorities and monitor progress toward goals.
• Collaborate with the Principal to ensure evening program instruction and culture mirror YouthBuild’s core model.
• Develop a comprehensive student onboarding and orientation process for all new evening students.
• Create systems for staff coaching, evaluation, and instructional development.
• Integrate restorative practices across instructional and community spaces.
• Spend structured time in the day program to learn YB’s instructional model, policies, culture systems, and community agreements.
• Collaborate with Human Resources to hire, onboard, and supervise all evening program staff.
• Lead ongoing coaching, feedback, and professional development for the evening team.
• Build a supportive, accountable, mission-aligned staff culture.
• Support staff in developing trauma-informed and equity-centered practices.
• Serve as the instructional and cultural leader of the evening program starting September 2026.
• Ensure clear, fair, and consistent school wide policies for the evening program.
• Lead culture-building experiences that promote student belonging and leadership.
• Gather and use student, staff, and community feedback to strengthen programming.
• Maintain a visible presence for students and staff and participate in community experiences across both programs.
• Lead evening school recruitment, outreach, and enrollment to ensure full evening program enrollment annually.
• Build partnerships that expand program capacity and support student success.
• Collaborate with Operations, Workforce, and Program teams to meet recruitment and placement goals.
• Partner with the Chief of Staff & Strategy to ensure operational readiness, safety, and compliance.
• Contribute actively to the school leadership team and schoolwide planning.
• Manage program budgets with strategic stewardship.
• Represent YouthBuild as an evening program leader, when needed.
• Mentor students and alumni and engage regularly with young people.
• Provide seamless coverage and schoolwide leadership support when the Principal is out of the building.
• Perform other duties as assigned by the Principal or Leadership Team.

Benefits

• Generous time off
• Medical, dental, and vision insurance
• Flexible spending accounts
• 401(k) savings plan with an employer match
• Employer paid parental leave, life insurance, short-term disability and long-term disability
• Educational assistance and professional development opportunities to enhance skills and career growth
• Supportive and collaborative work environment
• Strong community support and involvement

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Number of Employees: 101-250 employees