Executive Director, Cabrini Green Legal Aid

Flexibly Focused • Chicago, IL

10d • Hybrid

About The Position

Cabrini Green Legal Aid (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.

Requirements

• Proven and mission-driven operator, fundraiser, and people leader.
• 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.
• Excellent financial acumen.
• 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.
• Keen analytic and problem-solving skills with sound judgment in balancing near-term operational realities against long-term mission stability.
• 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.
• 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.
• 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.
• 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.

Nice To Haves

• Experience working in partnership with social workers and related professionals is preferred.
• Illinois law licensure and/or deep familiarity with the Cook County legal landscape is strongly preferred.
• Working with a Board of Directors to set and monitor goal progress is a significant plus.
• Experience managing government contracts and grants, and associated compliance requirements, is a plus.
• Prior experience as an Executive Director or in a comparable role is preferred.
• Relevant advanced degree (e.g, MBA, MSW, JD) is strongly preferred.

Responsibilities

• Serve as the public face of the organization’s fundraising efforts.
• 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.
• Manage large and complex budgets (particularly for nonprofit organizations with diverse or government-dependent funding streams).
• Perform revenue and expense forecasting, manage budget changes, and lead organizations through revenue-positive cycles and periods of fiscal discipline and operational adjustment.
• Set organization- and/or team-wide strategic priorities and consistently monitor and report progress.
• Work with a Board of Directors to set and monitor goal progress.
• Cultivate, solicit, and successfully secure five- and six-digit philanthropic gifts from private individuals and families.
• Secure philanthropic gifts/investments from corporate and/or foundation partners; build lasting positive relationships with key decision makers.
• Diversify 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.
• Manage government contracts and grants, and associated compliance requirements.
• Work with and manage volunteers, including Boards and committees.
• Hire, mentor, and retain employees, ideally in diverse roles.
• 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.
• Attend and participate in various meetings (including occasional evenings and weekends) on- and off-site, with internal and external stakeholders.

Benefits

• Blue Cross Blue Shield health insurance (with a 100% employer-paid premium option for the employee + family)
• Vision insurance
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive