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.

Overview

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.

Responsibilities

Multi-Entity Strategic Leadership & Enterprise Governance

• 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 authorizers (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.

Financial Operations & Budgeting

• 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 QuickBooks.

• 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.

Compliance, Revenue & Grant Management:

• 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 opinions, and no material findings.

• Payroll Oversight: Oversee payroll process and compliance in partnership with the HR and Talent team, improving accuracy, efficiency, and the employee experience.

• Future Growth: Build working knowledge of new funding and regulatory environments as the network considers future growth.

Team Leadership & Capacity Building:

• Team Management: Directly lead, mentor, and inspire the finance and accounting team to deliver high performance, clear communication, and customer-service-oriented support to campuses, and shape a team structure matched to the network’s current size and direction.

• School Leadership Support: Train and coach School Leaders and operational teams on financial processes, budget management, and efficient resource allocation.

Requirements:

Education

• Bachelor’s degree in accounting, finance, or a related field required; master’s degree (MBA or MAcc) preferred

Qualifications

• Ten or more years of progressive finance and accounting experience, including at least five years in a senior leadership role such as CFO, VP of Finance, or Controller

• CPA or CMA strongly preferred

• A record of leading annual audits to clean opinions, ideally including federal single audits

• Deep knowledge of nonprofit fund accounting, GAAP, restricted funds, and public funding compliance

• Hands-on experience with accounts payable, accounts receivable, procurement, payroll and accounting operations

• Experience reporting to a board or finance committee and leading a finance team through change

• Finance leadership in a charter network, school district, or education nonprofit (preferred)

• Familiarity with Illinois public education funding and CPS charter finance (preferred)

• Experience with multi-entity organizations or shared-services models (preferred)

• Strong ethics, with an ability to manage confidential data

• Technology demands

  • Proficient in Excel, Google Suite and new and existing Accounting software (Intacct, QuickBooks, and ADP)

  • Exceptional/Advanced Excel Budget Modeling experience

  • Excellent analytical and numerical skills

• Travel as needed for meetings and professional development

• Required in person 3-4 days a week

• Chicago-area residency, or willingness to relocate

Physical Demands:

Work is typically performed in an office setting with occasional extended periods of time at computer terminals. Occasional visits to off-site or campus locations is required. Generally, the job requires 60% sitting, 20% walking, and 20% standing.

Benefits

• 20+ paid holidays
• 12 weeks family paid leave
• Comprehensive Healthcare (Medical, Dental, Vision)
• 403b match
  • Fully match up to 3%
  • 50% match up to 5%
• Professional development including tuition reimbursement
• Gym and wellness discounts
• And more

Job Description Disclaimer: Since no job description can detail all the duties and responsibilities that may be required from time to time in the performance of a job, duties and responsibilities that may be inherent in a job, reasonably required for its performance, or required due to the changing nature of the job shall also be considered part of the jobholder's responsibility.

EEO: Distinctive Schools is an equal opportunity employer and does not discriminate against any employee or applicant for employment on the basis of race, color, religion, sex, gender, national origin, age, disability, veteran status, marital status, sexual orientation, gender identity, gender expression, or any other personal characteristic protected by applicable law.

Distinctive Schools is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Distinctive Schools will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact talent@distinctiveschools.org or call 773.828.4191