Executive Director

The Opportunity and the Ideal Candidate

Cabrini Green Legal Aid (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.

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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.

• 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.