Executive Director - Chicago

Overview

This role leads College Possible Chicago, guiding fundraising, programs and operations to advance local impact and provide an exceptional experience for students, families, donors and community partners. The Executive Director contributes to national strategy as a member of the Senior Leadership Team and serves as the external face of College Possible in the Chicago region.

Working at College Possible isn’t just a job — it’s a mission. You’ll play a direct role in helping students achieve educational goals, contribute to a national movement to expand college access, and help shape brighter futures.

As Executive Director of College Possible Chicago, you will:

• Lead site fundraising, programs and operations to drive local impact and exceptional experiences for students, families, donors and community partners.
• Ensure Chicago regional priorities and initiatives align with College Possible’s national strategy; participate on the Senior Leadership Team to contribute to national alignment.
• Represent College Possible externally, guiding fundraising activities, community outreach and collaboration with the local advisory board to support strategic goals.

• Develop and execute strategies that advance the organization’s mission, ensuring College Possible students earn admission to and graduate from college at comparable rates to their high-income peers.
• Cultivate relationships with diverse stakeholders to secure a $4.3M annual budget for fiscal year 2026 and grow year over year.
• Lead a Chicago team of 45 people (including 23 Ameri Corps members), ensuring staff have support and guidance to achieve outcomes for students.

• Provide strategic and operational leadership to align programs, staff and systems with the mission and impact goals.
• Collaborate with national services (HR, IT, finance/accounting, and other departments) to ensure smooth local operations.
• Drive regional outcomes and evaluation across fundraising, programming and staff engagement using data and continuous improvement.
• Bridge local and national perspectives through strong collaboration with the National team and alignment with broader priorities.
• Inspire staff, board members, donors and partners through vision, communication and relationship-building; build strategic partnerships to expand reach and impact.
• Provide financial oversight by managing budgets, monitoring performance and ensuring responsible resource allocation.
• Lead and support a diverse, inclusive culture focused on accountability and ambitious results.
• Guide growth and change with innovation and change-management practices.

• Lead fundraising efforts for College Possible Chicago in partnership with the Development Team to meet immediate revenue targets and long-term sustainability.
• Partner with the Chicago Advisory Board to leverage networks for resource cultivation and visibility.
• Engage your networks to broaden reach, amplify fundraising opportunities and strengthen community connections.
• Oversee marketing and communications; serve as the external ambassador to elevate the brand and position College Possible as a thought leader in education access.
• Build and steward relationships with individual donors, foundations and corporate partners for substantial, multi-year commitments.

The Executive Director will be a bold, innovative, mission-driven leader who seeks to expand educational access. The ideal candidate will be authentic, ethical and collaborative, with the following qualifications:

• A bachelor’s degree and authorization to work in the United States.
• 8–10 years of relevant leadership experience with a track record of building positive culture.
• Proven ability to achieve ambitious goals and drive measurable results through strong management and strategic execution.
• Skilled people manager who invests in professional growth and fosters accountability while motivating teams.
• Demonstrated fundraising success, including securing a six-figure gift and expanding a donor base; experience with Chicago funders is preferred.
• Adept at cultivating relationships with stakeholders…