Executive Director - Chicago at College Possible Leadership Team

This Work Is Our Mission

As one of the first and largest college access and success organizations in the country, College Possible has spent 25 years helping students turn their college dreams into reality. We've supported over 100,000 students nationwide - and counting - and have been recognized by Inside Higher Education, Time, Forbes, USA Today, and The Wall Street Journal for our impact and innovation.

At College Possible, we believe talent is universal. For many students, the path to college can feel overwhelming or out of reach. That's where you come in. We provide students with personalized coaching, guidance, and resources. When you join our team, you help students navigate admissions, overcome challenges, and earn their degrees - making college access and success a reality.

College Possible National Impact

At College Possible, the work you do directly contributes to measurable student and alumni success:

• Since 2000, we've supported 100,000+ students, helping them navigate the path to and through higher education.
• Students and alumni have attended 866 colleges and universities across the U.S.
• Students are 3X more likely to earn a bachelor's degree within six years.
• Strong alumni outcomes: based on an alumni survey, 95% are employed, 83% feel fulfilled in their careers, and 79% have improved their financial future.

Why Join Our Team?

Working at College Possible isn't just a job - it's a mission. You'll play a direct role in helping students achieve their educational goals, paving the way for brighter futures, and being part of a national movement to expand college access and success.

Your Role as Executive Director

As Executive Director of College Possible Chicago, you will lead the site's fundraising, programs, and operations, driving local impact and ensuring an exceptional experience for students, families, donors and community partners. While ensuring Chicago regional priorities and initiatives are successfully implemented, you will also serve on College Possible's Senior Leadership Team, contributing to national strategy and alignment. Building on the organization's strong regional foundation from the past 11 years, you will serve as the external face of College Possible. This includes leading all fundraising activities, community outreach efforts and collaboration with the local advisory board to:

• Develop and execute strategies that advance the organization's mission, ensuring College Possible students earn admission to and graduate from college at the same rate as their high-income peers.
• Cultivate relationships from a wide range of stakeholders, to secure a $4.3M annual budget for fiscal year 2026 and growing year-over-year.
• Inspire and lead a high-performing Chicago team of 45, including 23 AmeriCorps members, ensuring the staff have the support and guidance needed to achieve ambitious outcomes for students.

The Executive Director is integral to the culture, effectiveness, and impact of College Possible:

Site Management and Leadership

• Provide strategic and operational leadership for College Possible Chicago, ensuring programs, staff and systems are aligned to advance the mission and deliver impact.
• Collaborate with national centralized services to handle human resources, information technology, finance/accounting and other national departments as needed to ensure smooth execution of local operations.

• Drive regional outcomes and appropriate evaluation across fundraising, programming and staff engagement by focusing on high-priority goals, championing continuous improvement and using data to guide decision-making.
• Bridge local and national perspectives by maintaining strong collaboration with the National team, aligning regional work with broader organizational priorities and long-term goals.
• Inspire and motivate staff, board members, donors, and community partners through clear vision, effective communication, and relationship-building. Build and sustain strategic partnerships with stakeholders to expand the organization's reach and impact.
• Provide financial oversight by managing budgets, monitoring performance and ensuring responsible resource allocation.

• Lead and support a diverse team, fostering collaboration, accountability, and a strong, inclusive and mission-driven culture to achieve ambitious results. Ensure staff feel connected, empowered and motivated.

• Provide financial oversight by managing budgets, monitoring performance and ensuring responsible resource allocation.

• Guide the organization through growth and change with innovation, adaptability and strong change-management practices.

Fundraising and External Relations

• Lead fundraising efforts for College Possible Chicago, partnering with the Development Team to design and execute strategies that achieve both immediate revenue targets and long-term sustainability.
• Partner with the Chicago Advisory Board to leverage their networks and expertise in cultivating relationships, securing resources and expanding organizational visibility across Chicago.
• Engage and activate your own professional and personal networks to broaden the organization's reach, amplify fundraising opportunities and strengthen community connections.
• Oversee marketing and communications and serve as the primary external ambassador to elevate the brand: represent the organization at community events, engage with key stakeholders and media efforts and position College Possible as a thought leader on education and college access.
• Build and steward strong, lasting relationships with individual donors, foundations and corporate partners, securing substantial and multi-year commitments to advance the mission.

Who Should Apply

The Executive Director of College Possible Chicago will be a bold, innovative, and mission-driven leader who is energized by the opportunity to expand educational access and success for students. The ideal candidate will be an authentic, ethical and collaborative leader who possesses:

• A bachelor's degree and authorization to work in the United States.
• At least 8–10 years of relevant leadership experience, including success as a senior leader and demonstrated ability to build and sustain a positive organizational culture.
• A proven record of achieving ambitious goals and driving measurable results through strong management and strategic execution.
• Skilled people manager: adept at recognizing strengths, investing in professional growth and fostering accountability while motivating teams to achieve results.
• Demonstrated fundraising success, including securing a six-figure gift, expanding and diversifying an organization's donor base across individual, corporate and foundation funding streams; experience with the Chicago funder community is strongly preferred.
• Adept at cultivating and sustaining relationships with a broad range of stakeholders, including staff, board members, community partners, schools and higher education institutions.

Computer/Software Skills

• Strong computer skills, including demonstrated proficiency in Microsoft Word, Excel, PowerPoint, Office, and experience in database management. SalesForce experience a plus.

Physical Requirements

• Ability to lift up to 15 pounds when needed.
• Office environment with limited travel.
• Ability to stand and/or sit for a minimum of 7 hours a day

What We Offer

As a committed, diverse, values-based organization, we offer:

• A competitive salary commensurate with experience.
• Excellent benefits including complete health, dental, life, short-term and long-term insurance.
• 401(k) retirement plan.
• Encouraged sustainability through a generous paid time off program.
• Personalized professional development and growth opportunities.
• An opportunity to have a tremendous impact both internally and across the country.

To Join Our Growing College Possible Team

Please apply online at www.CollegePossible.org/careers which includes submitting your resume and cover letter.