Jobs at Distinctive Schools

The Dean of Students leads school culture, discipline, attendance, safety, and behavioral support initiatives. They supervise the School Culture Team, coach teachers on classroom management, resolve conduct incidents, monitor attendance and discipline data, oversee safety personnel, and collaborate with students, families, teachers, and student services staff. The role also supports IEP/504 meetings, develops behavior plans, prepares reports, and performs additional school-wide operational duties assigned by the Principal.

Provides front-desk, administrative, communications, records, scheduling, data-entry, cash-handling, food-service, registration, supply-ordering, and visitor-monitoring support for a high school campus. Serves families, students, staff, and visitors; maintains records and attendance information; supports the principal and campus operations team; and helps ensure safe, organized school operations.

The Chief Financial Officer leads enterprise financial strategy, budgeting, forecasting, cash flow, audits, compliance, grants, revenue optimization, procurement, payroll oversight, and multi-entity reporting. The CFO advises the CEO and board, manages partner and authorizer relationships, oversees finance systems and controls, and leads a service-oriented finance team supporting schools and affiliated organizations.

Oversee special education compliance across multiple Chicago school campuses, including IEP reviews, reevaluations, documentation audits, data integrity, student progress monitoring, and regulatory adherence. The manager supports principals, case managers, educators, families, and related-service providers; supervises and coaches case managers; coordinates provider staffing; facilitates meetings and training; and serves as a liaison with authorizers, local education agencies, and state officials.