Executive Director, Cabrini Green Legal Aid

Candidate Profile
Executive Director, CGLA

About Cabrini Green Legal Aid (CGLA)

CGLA was established in 1973 to serve legal needs arising from the lack of opportunity, criminalization  of poverty, and racial inequity experienced within Chicago’s Cabrini Green community. Since then, CGLA has grown beyond a single neighborhood to become a recognized citywide and statewide leader in supporting low-income individuals negatively impacted by the criminal justice system.
 

CGLA envisions a more just and equitable criminal legal system led and informed by those directly impacted. CGLA seeks to accomplish this vision through a three-pronged approach: providing holistic legal and social work services; advancing justice-focused policy and advocacy efforts; and building community and peer supports. 

Since its founding, CGLA has helped more than 170,000 people stabilize their lives by removing barriers to economic opportunity, strengthening families, and preventing homelessness. It is the statewide leader in criminal records relief services, which have been an integral part of its expansive partnerships with social service agencies. Notably, CGLA was an integral advocate for Illinois’ Clean Slate Act, which was signed into law in 2026, and expects to see its work transform over the next decade as record sealing becomes automated for most individuals.

CGLA has a professional staff of 40+ ; a  robust network of volunteer attorneys, social workers, and law and policy students; and an annual operating budget of approximately $5 million. A highly engaged group of volunteer leaders– including the Governing Board, Associate Board, and Leadership Council– also dedicate their time, professional expertise, and lived experience to help guide the organization’s work.

The Opportunity and the Ideal Candidate 

CGLA seeks a proven and mission-driven operator, fundraiser, and people leader to serve as its next Executive Director. This leader will leverage CGLA’s 53-year legacy of sector-wide influence to set a clear strategy for and execute efficiently against the organization’s next phase of impact, with a particular focus on strengthening CGLA’s financial foundation and long-term organizational stability. This includes serving as the public face of the organization’s fundraising efforts.

CGLA’s next Executive Director will possess these key abilities and traits:

Legal Savvy and Community-Centered Commitment to Systemic Transformation

• Personal and/or professional connection to the lived experiences of CGLA clients; experience working with and in service to historically disenfranchised communities 
• Experience engaging and working alongside diverse partners, including community-based organization staff, individuals impacted by the criminal legal system, elected officials, and government partners, and members of the criminal justice reform ecosystem 
• Commitment to working within an interdisciplinary organizational model;  experience working in partnership with social workers and related professionals is preferred
• Strong working knowledge of the criminal justice and/or legal aid sectors; Illinois law licensure and/or deep familiarity with the Cook County legal landscape is strongly preferred 

Strong Operator 

• Excellent financial acumen: strong experience setting and managing large and complex budgets (particularly for nonprofit organizations with diverse or government-dependent funding streams)
• Experienced planner: proven history of revenue and expense forecasting, managing budget changes, and leading organizations through revenue-positive cycles and periods of fiscal discipline and operational adjustment
• Goal setting and tracking proficiency: successful track record of setting organization- and/or team-wide strategic priorities and consistently monitoring and reporting progress
  • Working with a Board of Directors to set and monitor goal progress is a significant plus
• Keen analytic and problem-solving skills with sound judgment in balancing near-term operational realities against long-term mission stability.

Skilled Fundraiser and External Lead

• Proven track record of cultivating, soliciting and successfully securing five- and six-digit philanthropic gifts from private individuals and families 
• Proven track record of securing philanthropic gifts/investments from corporate and/or foundation partners; success building lasting positive relationships with key decision makers
• Demonstrated success diversifying organizational revenue streams, with particular interest in candidates who have reduced reliance on government funding through growth in individual giving, planned giving/bequests, and private foundation support
• Experience managing government contracts and grants, and associated compliance requirements, is a plus
• Experience working with and managing volunteers, including Boards and committees

Inspirational and Effective People Manager

• Successful track record of hiring, mentoring, and retaining employees, ideally in diverse roles
• Proven track record of high employee satisfaction in prior management role(s)
• Excellent internal communications skills with clear decision-making processes and consistent employee engagement 
• Ability to integrate confidence as a manager with the empathy required to clearly and positively lead a team forward 

Required Qualifications

• Established people management experience; prior experience as an Executive Director or in a comparable role is preferred
• Unwavering commitment to criminal justice reform and the clear understanding of the deep and systemic challenges that serve as current barriers
• Direct experience managing nonprofit budgets, cash flow, and financial oversight
• Experience partnering with a volunteer Board of Directors and/or lay committee(s)
• High emotional intelligence; demonstrated ability to effectively adapt to the diverse needs of varied partners, including clients, donors, staff, and government representatives
• Bachelor’s degree and sufficient relevant professional experience; relevant advanced degree (e.g, MBA, MSW, JD) is strongly preferred 

Salary and Benefits

• Total compensation is in the $170,000 - $190,000/year range, commensurate with experience 
• CGLA provides a comprehensive benefits package, which includes:
  • Blue Cross Blue Shield health insurance (with a 100% employer-paid premium option for the employee + family), vision insurance, and dental insurance
  • 100% employer-paid life insurance
  • Dependent care and medical flexible spending accounts 
  • Pre-tax programs for parking, public transit, and UberPool
  • Optional participation in a Vanguard 403(b) retirement plan, including organization match
• Generous paid time off, including “Summer Fridays”, Wellness Days, and a paid office-wide closure the last week of the calendar year.

Work Environment and Requirements

The Executive Director is expected to:

• Communicate clearly and effectively, in writing and orally, with a wide range of internal and external parties, including, without limitation, employees, leaders, Board members and outside relations of CGLA. 
• Regularly work from our Chicago office (approximately 2 - 3 days/week on average). .  
• Reliably attend and participate in various meetings (including occasional evenings and weekends)  on- and off-site, with internal and external stakeholders.
• Occasionally travel (within and outside of the Chicagoland area) utilizing reliable personal transportation 

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Applications will be reviewed on a rolling basis until this position is filled; for best review, potential candidates are encouraged to apply by August 30, 2026.

All inquiries and applications will be held in the highest confidence. To apply, please submit a targeted cover letter and resume via the provided link; no phone calls, please.