Jobs at Cabrini Green Legal Aid (Now Hiring) — 2 open

Position Overview

CGLA seeks a strategic, forward-thinking Fractional CFO with deep experience in nonprofit accounting, cash flow modeling and projection, grant reporting and compliance, organizational budget management, and financial systems integration. This role, reporting to the Executive Director, is critical in ensuring financial sustainability, optimizing financial operations, and supporting strategic growth.

The Fractional CFO will support our existing Senior Accountant and Finance Team, working closely with the Executive Director and Board of Directors to strengthen financial reporting and risk management while aiding leadership to make more informed decisions.

The ideal candidate will provide high-level financial strategy, build upon predictive cash flow models, add support an in-progress transition to an automated payment and reimbursement system, strengthen organizational budget management and internal controls, and provide mentorship and guidance our existing finance team.

CGLA seeks leaders who demonstrate cultural humility, a commitment to justice, and the ability to work effectively supporting communities disproportionately impacted by the criminal legal system.

Key Responsibilities

1. Strategic Financial Leadership & Modeling

• Strategic Advisory: Partner with the Executive Director, Board of Directors, and staff Finance Team to translate complex financial data into actionable, mission-aligned strategy.
• Budget and Cash Flow Architecture: Help refine organizational budgeting structure and management process; improve predictive cash flow forecasting to navigate the timing gaps inherent in institutional and reimbursement-based grants.
• Finance Committee Support: Support the Senior Accountant in creating monthly financial reports for the Board and Executive Leadership. Augment regular reports with predictive and analytical reports, management dashboards, and provide guidance for organizational leadership to help manage budget and expenditures. Attend monthly Finance Committee meetings as appropriate.
• Financial Management: Provide guidance on financial policies and procedures, expense management, and cost reductions. Review cash management strategies and accountability systems for A/R and A/P execution. Support Senior Accountant in strengthening internal controls, ensuring segregation of duties, fraud prevention measures, and financial risk mitigation strategies.

2. Team Leadership, Systems Integration & Operational Overlap

• Systems Oversight: Provide strategic oversight of financial system integrations, ensuring alignment between finance, operations, and development workflows.
• Supervisory Scope: Provide dotted‑line oversight and mentorship to finance staff; collaborate with the Executive Director on performance expectations and capacity‑building needs.
• Migration Leadership: Help support and guide our transition to the Rippling Expense management platform.
• Data Workflow Optimization: Design and implement seamless automated data flows syncing Rippling payroll and expenses directly into QuickBooks Online.
• Banking Systems Transition: Advise organizational leadership on a banking systems transition and support implementation of the process. 
• Team Mentorship: Provide structural oversight, support, and training to our Finance and Operations teams to ensure smooth operational adaptation to new software.

3. Grant Compliance & Accounting Oversight

• Grant Tracking Architecture: Analyze existing set up and help ensure QuickBooks is structured efficiently (using classes, projects, or tags) to track restricted grant funds.
• Reporting & Compliance: Partner with Senior Accountant to create and/or maintain financial reporting deliverables for grant applications, renewals, and general compliance.
• Audit Readiness: Provide support to Senior Accountant to ensure compliance with GAAP and nonprofit regulations, proper year end close functions, and generally ensure a clean annual audit trail.
• General Reporting: Collaborate with Finance, Operations, and Development teams to prepare budget update, financial narratives, and other financial reports.
• Restricted Funds Management: Help monitor and track restricted and unrestricted funding.
• General Compliance: Ensure Compliance with non-profit accounting standards, GAAP, and grant requirements (for State, County, City of Chicago – with federal pass through as well as private foundation grants.

Qualifications & Experience

• CPA, CMA, or MBA in Finance.
• Experience: 10 years of relevant experience with 7+ years of senior financial leadership experience (CFO, VP of Finance, or equivalent).
• Nonprofit Expertise: Proven mastery of restricted fund accounting and compliance for complex grant portfolios ($5M+ budget size preferred); Knowledge of government (State, County, and City) and philanthropic grant reporting.
• Tech Mastery: Deep, practical experience configuring and optimizing payroll & Expense/Spend management; Proficiency in QuickBooks.
• Systems Migration: Demonstrated success leading a team through accounting software or expense system implementation.
• Communication: Exceptional ability to articulate complex financial concepts to non-financial staff, board members, and external donors while exhibiting patience with non-financial staff.
• Data Skills: Strong financial modeling, strategic thinking, nonprofit acumen, and data analysis skills.
• Mission Alignment: Demonstrated commitment to systemic change of the criminal legal system, support for racial and economic justice, and community‑based nonprofit work.
• Board Engagement: Experience preparing and presenting financials with actionable insights and analysis to nonprofit boards and leadership staff.

Compensation & Commitment

This is a part-time, contract-based position with an estimated commitment of 35-45 hours per month (or 8-12 hours per week). This role is structured as a fractional executive engagement and does not include employee benefits. Compensation is $4,500 to $7,500/month, commensurate with nonprofit financial management experience.