School Principal

ChanceLight Programs•Chicago, IL

5d•$90,000

About The Position

Ombudsman Educational Services , a growing, dynamic organization with a social mission to offer hope, is seeking a School Principal to join our award-winning Alternative Education team and perform meaningful work in a culture that welcomes innovation, encourages creative expression and offers limitless potential for personal and professional satisfaction! If you thrive in a fast-paced, student-centered, outcomes-driven environment, enjoy leading teams and strengthening instructional quality, and bring a solutions-first mindset, a sense of humor, and a rock-solid work ethic — We Should Talk! As the School Principal , you will serve as the instructional driver and operational leader of the site — owning High School student achievement by ensuring high-fidelity implementation of Ombudsman’s endorsed instructional practices, expectations, and procedures. You will coach and develop staff, set a clear vision for teaching and learning, and use data to strengthen instruction, accelerate growth, and remove barriers to success. In parallel, you will oversee day-to-day site operations — staffing, scheduling, safety, compliance, and facilities — creating a structured, supportive environment where students and staff can thrive.

Requirements

Master's degree or higher in education or a closely related field of study.
Licensed currently or in the process of obtaining a valid state teaching credential.
Licensed currently or in the process of obtaining an IL Administrative Endorsement.
Prior experience and/or knowledge in alternative educational services for at-risk youth and working with students with diverse needs at various levels.
Effective management skills and comprehensive knowledge of administrative and school operations, functions, and compliance requirements.
Prior experience and highly knowledgeable in the development, assessment, and management of curriculum, content areas and instruction.
Well-versed in effective teaching strategies, classroom management systems, data-based decision making, differentiated instruction and working with students with individualized education plans (IEP's).
Prior experience and highly skilled in providing professional development and/or coaching to teachers and education staff.
Proficiency in providing motivation and having critical conversations with students that help move them toward realistic goals.
Prior experience and highly skilled in crisis management systems and intervention.
History of success building credibility, effectively managing multiple projects and collaborating effectively across all organizational levels.
Highly skilled in building relationships with students, parents, teachers and community and/or district partners.
Advanced oral and written communication, organization, conflict resolution, multitasking, problem solving, and decision-making ability.
Knowledge of relevant technology including experience with instructional technology, Microsoft Office Suite, database entry and basic office equipment.
Skilled leader who exhibits the characteristics of servant leadership, looking to the needs of the team and seeking to help solve problems and promote personal development.

Responsibilities

Driving student achievement by ensuring consistent, high-fidelity implementation of Ombudsman-approved instructional practices, strategies, and site expectations.
Leading as the site’s instructional anchor by supervising staff, strengthening daily instruction, and ensuring policies and procedures are executed with consistency, urgency, and care.
Overseeing all site operations while serving as the primary liaison to school district contacts, building positive, interactive relationships that support shared student success.
Setting a clear vision for instructional excellence and efficient operations by developing performance plans, identifying professional learning priorities, and modeling a continuous-improvement mindset.
Delivering individual and group counseling supports to address barriers to learning, including crisis intervention consultation and/or family-focused support as needed.
Participating in hiring and selection processes to build and retain a high-performing, student-centered site team.
Guiding teachers in developing schedules, maintaining student data systems, and executing transition plans aligned to each student’s goals and services.
Coaching teachers in classroom-based strategies that build student social skills, problem-solving abilities, and conflict resolution competencies.
Supervising staff through clear work direction, individualized development planning, ongoing feedback, and consistent evaluation focused on growth and results.
Recognizing team accomplishments and addressing performance or operational gaps promptly to sustain a productive, positive, and accountable site culture.
Ensuring a safe, supportive learning environment by maintaining strong site and classroom operations and following required incident response and reporting procedures.
Maintaining compliance with contract and state requirements by ensuring staff understand performance criteria, implementation expectations, and accountability measures.
Managing core operational functions—including staffing, scheduling, technology, and facilities—to keep the site running smoothly and student-focused.
Representing Ombudsman with professionalism and credibility at community, district, and local levels to strengthen partnerships and program impact.
Communicating consistently and collaborating effectively with families, district partners, and community stakeholders to align supports and reinforce student success.
Analyzing professional development needs and aligning training to the instructional vision, Ombudsman priorities, and district goals.
Demonstrating strong leadership, team-building, and communication skills to inspire performance, clarity, and collaboration across the site.
Instructing staff and monitoring implementation of learning materials and instructional tools to ensure fidelity, student engagement, and measurable progress.
Observing and evaluating staff and student performance while documenting outcomes and reinforcing growth plans through actionable coaching.
Maintaining accurate student records and progress documentation in alignment with legal requirements, Ombudsman policies, and district procedures.
Compiling and analyzing assessment data to measure growth, guide instruction, and inform academic interventions for students and the broader site.
Modeling and reinforcing Ombudsman instructional practices that promote active learning, engagement, and alignment to the site’s instructional vision.
Managing student behavior using Ombudsman philosophy and policies while delivering proactive supports, academic counseling, and student encouragement.
Participating in quality assurance, accreditation, and performance review processes to ensure the site meets or exceeds required standards.
Staying current on research-based practices and organizational initiatives (including CPI) to strengthen safety, instruction, and student outcomes.
Providing and soliciting constructive feedback to build transparency, accountability, and a culture of continuous improvement.
Collaborating across site, field, and national teams to share best practices, solve problems quickly, and advance organizational goals.