Managing Director of College Success

Job Type

Full Time



Application Deadline



247 South State Street
Suite 700
United States


About Chicago Scholars

Chicago Scholars is transforming the leadership landscape of our city by resolving the fundamental barriers to success for academically driven, first generation college students from under-resourced communities. Through college counseling, mentoring, and by providing a supportive community to our Scholars through each phase of our program: College Access (Launch), College Persistence (Lift) and College to Careers (Lead), we ensure that they realize their full potential as students and leaders.

86% of Chicago Scholars graduate college within 6 years. Per the University of Chicago Consortium on Chicago School Research, only 49% of their peers earn a degree within 6 years. Upon graduation, our Scholars move into leadership positions across Chicago, helping to drive the economic future of their communities and our thriving city.

Our Values

These are a set of guiding principles that apply to all stakeholders within the Chicago Scholars ecosystem. We select and retain stakeholders based on these stated expectations for how we achieve our mission and vision. Each are supported with core competencies and narrative for the sake of clarity.

We Dream Big. We speak up, innovate, push the boundaries and keep the creativity flowing. We don’t accept the status quo because the stakes are too high. We have an incredible belief that growth and change is possible. While we dream big, we are laser focused on our intended goals and outcomes for our Scholars, our city and the world.

We Show Up. We show up every day; not just physically, but with a positive attitude and willingness to work, connect, challenge, engage, solve problems and have fun. We don’t wait for someone to tell us what to do. We take action and get the job done. If we don’t know how, we figure it out through our knowledge, exploration or our network.

We Embrace Our Differences. We represent a multicultural nation and our collective backgrounds, experiences, styles, values, perspectives and beliefs are an asset to the world. We recognize that together we achieve better outcomes more quickly. Justice and equity starts with us using our collective voice.

We Model the Way. We exhibit the behavior that we want to see in others and in the world. Titles are granted, but our behavior is what earns us respect. In order to model the way, we must be clear about our guiding principles, celebrate our accomplishments and learn from our challenges and failures.

We Care For Each Other Along the Way. We adapt to the needs of the person in front of us. We pause, reflect and listen. We do our best work when we are in good relationship together. We care personally and challenge directly.

We Keep Our Word. When we commit, we are all in. Whether for events, a Scholar, a peer or ourselves. Our words are as powerful as our actions and are the building block of trust, respect, self worth and integrity.

Position Summary

The Managing Director (MD) of College Success will work in collaboration with the MD of Access and the MD of Partnerships to execute on the mission of the organization. The MD of Success will oversee all programs and supports to manage Scholars’ critical transitions from high school to college and college to career. This role will manage a growing team to build and sustain Scholar relationships and advocate for resources to ensure that Scholars persist and complete college to become the next generation of leaders. Strong candidates should be proficient in managing growth, change and ambiguity. All candidates should have demonstrated leadership, coaching, and relationship management experience. 

Key Responsibilities

Scholar Engagement: Oversee engagement and connection with our Scholars and the College Success Team to ensure that Scholars persist and are on track for graduation and career success.

  • Build cohorts for each team member to allow Scholars to build deep relationships with staff so that they will highlight their college challenges and career aspirations
  • Assist the team in prioritizing, scheduling, and participating in local campus visits to create community and deepen relationships between Scholars throughout Chicago and the Chicago Scholars team
  • Leverage technology to create personalized experiences for Scholars that are efficient and effective to maintain their engagement and connection 
  • Monitor Scholar inquiries and frequently survey Scholars to understand trends; continually evaluate staff training needs or changes required to redirect staff, partners and resources to address Scholar needs
  • Track Scholar enrollment data accuracy and completeness to ensure that we are on track per our persistence and graduation goals
  • Facilitate training and workshops to leverage relationships with Scholars to deliver content to support college matriculation, college success, career exploration and leadership development

Scholar Advocacy: identify resources to support Scholars, especially those who are at risk, and develop processes and systems to efficiently direct these resources to Scholars to ensure their matriculation, persistence, graduation and career launch

  • Continue to leverage the relationships of the College Access Mentors as Scholars transition from high school into their first year of college
  • Oversee the Peer Mentoring program to provide upper classmen pairings to help navigate the transition to campus and create a Chicago Scholars community
  • Lead Chicago Scholars financial assistance programs, including the coordination with grantors, advertising, Scholar selection, funds distribution, and reporting related to the college experience 
  • Highlight the campus resources needed by Scholars; coordinate with the Managing Director of Partnerships to fulfill these needs on local college campuses 
  • Work with the College to Careers team to provide career support, exposure, internships, resume reviews and career mentoring to college Scholars 
  • Continually monitor trends to identify new strategic training, programming, resources, supports and interventions needed for Scholar success

Strategic Thinking: Identifies opportunities for the organization to improve impact beyond own program area, and shares ideas with others. Weighs limitations like resources and staff when considering visionary ideas; can create big ideas but also understands implementation. Weighs limitations like resources and staff when considering visionary ideas; can create big ideas but also understands implementation

  • Support the Career and Leadership Development team with the long-term vision and execution of leadership development work for Scholars on college campuses across the nation 
  • Refine and establish programming related to college success expectations and leadership cultivation
  • Develop the necessary systems, processes, and tools to better support the facilitation, collection, and sharing of knowledge that is generated by college success programming
  • Understand data; analyze data and identify insights and implications. Fluent in organization-wide data (e.g. dashboards) and can speak to implications. Communicate implications of data within the broader organization and use data to help position future possibilities

Staff Development: Motivates others and supports their development through strong coaching and mentoring. Stays informed of development opportunities and resources within the organization and links staff to them where appropriate. Effectively addresses marginal and unsatisfactory performance

  • Manage a team (7 people) of Senior Managers, Senior Associates and Associates of varying professional experience to ensure staff pursue professional development opportunities
  • Experience successfully transitioning a team through an organizational change management process

Additional Responsibilities:

In addition to managing a team, this position will also require occasional work on nights and weekends for Scholar events and programming, and the facilitation of Scholar events and workshops. This role is also required to attend and support mandatory all staff events: the UnTied Gala, College Choice Celebration, New Student Orientation, All Scholar Retreat, First Look, the Onsite Admissions Forum, New Student Interview nights, and our Quarterly Staff Retreats. This role is also required to attend and support mandatory all Program team events: Chicago Scholars Day, and Scholar Holiday Party. 



  • Education: Undergraduate degree required, Master’s degree required
  • Experience:10-15 total, with 5-7 years of related programming experience, including managing a team of direct reports.

Core Competencies

  • Ability to communicate in a manner which consistently demonstrates respect, concern, and responsiveness
  • Ability to speak in public and engage all stakeholders (Scholars, parents, mentors, volunteers, college representatives)
  • Demonstrated ability to cultivate and sustain relationships with diverse audiences (educational level, socio-economic circumstance)
  • Demonstrated ability to work at a rigorous pace to manage multiple projects and meet deadlines.
  • Ability to work independently and collaboratively in a team environment.
  • Ability to remain flexible and adapt to changing needs and priorities.
  • Ability to track and interpret data for decision making and program/process evaluation.
  • Demonstrated management skills, including the ability to manage change and generate a culture of continuous improvement.
  • Ability to manage a budget to achieve defined goals and demonstrate a commitment to use resources effectively.
  • Ability to handle sensitive and confidential information with discretion
  • Ability to provide leadership in development of inter-team communication and cohesiveness, sustaining culture and supporting staff during organizational growth.

Professional Level

None specified

Minimum Education Required

4-year degree

How To Apply

- Please click 'Apply' to submit your application which should include a resume and cover letter.

- In your cover letter, please describe your experience supporting first generation college students to insure that they persist and graduate.  

- All Candidates must be available to interview on the following dates:

- Round 1, Tuesday 11/6

- Round 2, Tuesday 11/13

- Round 3, Monday 11/19