Chief Financial Officer

Job Title: Chief Financial Officer

Location: 910 W. Van Buren St., Chicago, IL 60607

Reports To: President & Chief Executive Officer

Salary: Starting at $200,000, commensurate with experience

Employee Type: Regular Full Time

Start Date: November 2026

Distinctive Schools creates diverse, joyful, welcoming communities rooted in social justice and rigorous learning. We support all learners to be engaged, curious, and to achieve their full potential. Our students become confident advocates, creative problem-solvers, and collaborative leaders.

The Chief Financial Officer (CFO) serves as a key strategic partner to the CEO, the LEAP Board of Directors, and the executive leadership team. Serving as the lead financial executive for Distinctive Schools, the CFO provides total fiscal oversight, strategic direction, and financial leadership for the network, including the accounting and financial services it provides to affiliated organizations.

This executive role safeguards the fiscal health of the enterprise, manages complex multi-entity reporting, ensures strict charter authorizer and non-profit compliance, and aligns resources to the strategic plan, positioning the network for long-term sustainability.

The network needs a leader who delivers timely, accurate information, explains complex tradeoffs in plain language, and builds a finance team grounded in service to schools.

• Lead Financial Executive Oversight:
  Serve as the chief financial officer for Distinctive Schools. Oversee the accounting and financial services the network provides to affiliated organizations, and manage the financial relationship with LEAP, including intercompany transactions and the integrity of separate books and reporting.
• Partner & Authorizer Relations:
  Manage financial reporting, compliance, and strategic alignment with partner organizations, school authorize rs (e.g., CPS/district reps), state agencies, and the LEAP Board and its committees.
• Board Reporting:
  Prepare clear, accurate financial reports and presentations for the CEO and the LEAP Board, translating complex information into plain language that supports sound decisions.
• Network Growth & Capital Strategy:
  Partner with executive teams and on long-term growth opportunities, philanthropic efforts, grant requests, debt management, and reserve strategies across all partner entities.

• Budget Oversight:
  Lead the creation, implementation, and frequent monitoring of annual operating budgets across network departments and school campuses, and build a multi-year financial model with enrollment-driven scenarios.
• Cash Flow & Forecasting:
  Lead the finance team in delivering monthly and quarterly cash-flow forecasts and scenario planning to the CEO and Board.
• Procurement & Vendor Management:
  Oversee procurement processes, vendor contracts, RFPs, leases, and financial systems and E-rate funding, including software such as Intacct and Quick Books.
• Systems Integration:
  Continually audit and optimize banking, accounting software, and data syncs across partners and teams, including integration between finance, payroll (ADP), and HR systems, to ensure seamless auditing and reporting.

• Revenue Optimization:
  Serve as the organization’s primary revenue expert—identifying, advocating for, and securing all eligible federal, state, and local funding sources.
• Grant & Partner Compliance:
  Ensure total operational and financial compliance for grants, title planning, reimbursements, accounts payable/receivable, and related reporting.
• Audit Leadership:
  Lead the annual audit, including the federal single audit, with the goal of on-time completion, clean…