Chief Financial Officer

Distinctive Schools; Chicago (IL); On-site; USD 180,000 - 220,000; Full time

Benefits offered by this job

20+ paid holidays

12 weeks family paid leave

Comprehensive Healthcare (Medical, R&D

403(b) match (fully up to 3% and 50%/5

Tuition reimbursement

Gym and wellness discounts

Job summary

Distinctive Schools is seeking a Chief Financial Officer to serve as a strategic partner to the CEO and LEAP Board, providing financial leadership for the network of affiliated organizations. The CFO will oversee accounting, reporting, and compliance while guiding multi-entity operations and long-term sustainability.

The role requires leading a finance team, ensuring accurate budgeting and forecasting, and optimizing revenue through government funding, grants, and partnerships.

Qualifications

• Bachelor’s degree in accounting, finance, or related field required; MBA or MAcc preferred.
• Ten or more years of progressive finance and accounting experience, including at least five years in a senior leadership role.
• CPA or CMA strongly preferred; record of leading audits to clean opinions, ideally including federal single audits.
• Deep knowledge of nonprofit fund accounting, GAAP, and public funding compliance.
• Hands-on experience with accounts payable/receivable, procurement, payroll and accounting operations.
• Experience reporting to a board or finance committee and leading a finance team through change.
• Familiarity with Illinois public education funding and CPS charter finance (preferred).

Responsibilities

• Lead multi-entity strategic leadership and enterprise governance for the network.
• Oversee budgeting across network departments and campuses; build multi-year models.
• Manage cash flow and forecasting; deliver monthly/quarterly projections to CEO and Board.
• Oversee procurement, vendor contracts, and financial systems integration (Intacct, QuickBooks, ADP).
• Drive revenue optimization across federal/state/local funding sources.
• Ensure grant & partner compliance and timely reporting; lead annual audit.
• Oversee payroll in partnership with HR; improve accuracy and efficiency.
• Build finance team capacity and train school leaders on budgets and resource allocation.
• Support future growth through new funding opportunities and regulatory changes.
• Travel as needed; in-person work 3–4 days a week; Chicago-area residency or relocation.

Skills

Financial leadership

Board reporting

GAAP knowledge

Nonprofit fund accounting

Audits & compliance

Multi‑entity governance

Excel modeling

Communication

Education

Bachelor’s degree in accounting or finance

MBA or MAcc preferred

Tools

Intacct

QuickBooks

ADP

Excel (Advanced)

Job description

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.

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.

• 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 [e-mail] or call 773.828.4191