Executive Director, iMentor Chicago

Job Type

Full Time



Start Date:



332 South Michigan Avenue
United States


About iMentor 

iMentor builds mentoring relationships that empower students from low-income communities to graduate high school, succeed in college, and achieve their ambitions. iMentor partners with public schools and matches every student in the school with a college-educated mentor who commits a minimum of three years to a single student. Mentor-mentee pairs work together through the iMentor curriculum, which is designed around four core outcomes: developing strong personal relationships between mentors and mentees, growing each mentee’s college aspiration, developing the non-cognitive skills critical to success in college, and successfully navigating the college exploration, application, financial aid, and transition process.

Since 1999, iMentor has connected more than 25,000 students with mentors. This year, iMentor is serving more than 600 mentor-mentee pairs in Chicago and 6,800 more nationwide. iMentor raised $2MM nationally to support the launch of iMentor Chicago in the fall of 2015, and the Chicago team raised $800K and tripled in size in its first year of operation, with staff coming from Urban Prep, Mikva Challenge, University of Illinois at Chicago, Teach for America, and the Illinois College Advising Corps.

iMentor has been recognized nationally through funding by the Bill & Melinda Gates Foundation, New Profit, the Lumina Foundation, the Michael & Susan Dell Foundation, and the Robin Hood Foundation, and was a subgrantee of the federal Social Innovation Fund. As a team, we are collaborative, fun, bring passion and joy to our work, and deeply believe in human potential. iMentor was recently named one of the Best Nonprofits to Work For by Opportunity Knocks and The Nonprofit Times. Read more about our work and values at: http://www.imentor.org

Position Overview

iMentor is seeking an exceptional Executive Director to lead its Chicago region. The Chicago ED will continue the launch and development of iMentor’s first direct service region outside of New York City, a key component of iMentor’s strategic plan and national growth. Reporting to iMentor’s national CRO (Chief Regional Officer), Adeola Whitney, the Chicago ED will set the strategic vision for iMentor’s work in Chicago while building and leading a high-performing team of 15 professionals. The ED will design and implement an effective local fundraising strategy that allows iMentor Chicago to grow from an approximately $1.1MM budget currently to $2.2MM annually in 2018. S/he will build a high impact local Advisory Board and partner closely with that group to ensure the organization meets or exceeds its goals.

The ideal Chicago ED candidate is a motivational and effective leader able to set and drive progress towards ambitious goals. S/he will be skilled in fundraising, nonprofit management, program implementation, and partnership development. S/he will be analytical, highly collaborative, and have a proven track record of establishing buy-in across stakeholders and influencing diverse groups of individuals and networks to achieve desired outcomes.


Fundraising and Board Development 

• Set and meet annual fundraising targets to support the growth of iMentor Chicago.

• Build and manage a high-impact local Advisory Board.

• Grow a sustainable, diversified local funding base (e.g., individuals, corporations, foundations, public funding etc.).

• Ensure the ongoing engagement and stewardship of an ever-growing portfolio of influential individual, corporate and foundation partners.

Leadership and Management 

• Lead an exceptional team of 15 full-time staff currently

• Foster a highly effective work culture with strong leadership development to all staff through quality coaching and feedback.

• Manage the site towards ambitious goals, using data-driven decision making to monitor and address problems, improve performance and increase sustainability.

• Cultivate internal and external talent required for the long-term success of the region.


• Oversee a high quality execution of the iMentor model in Chicago

• Develop and implement a three to five year growth strategy that aligns with the national strategic plan, scaling the program to serve 1,340 students annually by 2018

• Work closely with iMentor’s national team to adapt program offerings where necessary, with the goal of improving both efficacy and impact.

• Share best practices and key insights from the Chicago region with national team and future iMentor sites.

Partnerships and Communications 

• Serve as the key external voice and representative of iMentor in Chicago, demonstrating an exceptional and compelling articulation of iMentor’s work.

• Steward an effective partnership with local school districts and individual school partners to support progress towards iMentor Chicago goals.

• Develop and maintain relationships with key stakeholders across the public and private sectors. This will include: corporations, public officials, peer organizations, collective impact groups and networks, and affinity groups.

• Cultivate a local identity that is reflective of iMentor’s core values and culture.


• 8+ years in a senior management position in an education nonprofit organization, school district, foundation, government agency, or for-profit organization.

• Demonstrated success designing and executing high level fundraising strategies and strategic partnerships.

• 5+ years managing a layered team. Proven track‐record of managing, mentoring, and inspiring a high performing team to reach ambitious goals.

• Knowledge of and relationships within the Chicago educational, civic, philanthropic, and political landscapes.

• The ability to critically assess challenges and identify effective solutions.

• Outstanding inter-personal skills and the ability to build strong relationships with a variety of stakeholders.

• Aligned in thought and action with iMentor's values (http://www.imentor.org/values)

• Views differences between individuals (race, gender, age, cultural heritage, physical ability, education and lifestyle) as an asset and demonstrates an appreciation of the diversity within iMentor.

• Bachelor’s degree required

To Apply 

Visit www.imentor.org/jobs to submit a resume and detailed cover letter describing your interest in and qualifications for the position, as well as your salary requirements. Applications will be considered on a rolling basis, so it is in candidates’ best interest to apply as soon as possible. No phone, email, mail, or fax inquiries will receive a response.

iMentor is an Equal Opportunity Employer


• Salary commensurate with experience

• Up to 100% employer funded comprehensive medical and dental coverage

• 18 days paid annual vacation and 13 paid holidays

• 401K match up to 4%

• Significant opportunities for professional development and growth

Professional Level


Minimum Education Required

4-year degree

How To Apply