Vice President of Career and Leadership Development

Job Type

Full Time



Application Deadline:



247 South State Street
United States



Position: Vice President of Career and Leadership Development

Reports to: President & CEO

The Chicago Landscape

There is a deep reservoir of talent in this great city! In order to remain a world-class city, we must invest in talent from an education and leadership perspective. Locally and nationally, we are not fully equipping our youth with the skills and tools to be successful. Just 14% of Chicago Public Schools freshman will graduate with a college degree by the age of 25 per the University of Chicago Consortium of Chicago School Research. There also remains a lack of diversity in the workforce at all levels and in every industry. We must continue to invest in building a diverse pipeline of talent if we are to remain a vibrant, thriving and competitive city.

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.

88% 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 Future

Chicago Scholars is at a particularly exciting and critical juncture. Due to the success of our program, we have recently received support to expand our impact to serve 675 incoming students and a total student body of 4,500 by FY19.

We seek new members to the Dream Team who can help realize our vision for the future and who exemplify our core values, which do lead our work.

• Mission Driven: We must be relentlessly focused on our Scholars and their potential for success.

• Belief: We demonstrate a strong belief in our Scholars, our city and the potential that exists

• Excellence: We are intentionally in pursuit of quality inputs and outputs programmatically and operationally. Feedback collection is a critical part of a continuous improvement process in pursuit of that excellence. This also includes the demonstration of leadership, honesty, integrity, respect and equity.

• Data Driven / Results Oriented: We will use data to inform our program. We will have clear outcomes and response. We will use our data to demonstrate credibility and effectiveness as a high quality organization.

• Collaboration: We will collaborate internally among teams as well as externally within Chicago. Programmatically, we also recognize that we are just one part of a support system for our Scholars and we must collaborate with those organizations to support our Scholars.

• Innovation: We will always think about how to do things differently and more effectively. We will be thoughtful about how to use resources and technology to achieve growth and efficiency. We will focus on learning, questioning and forward thinking.

Position Summary

Our organization is growing rapidly and we recently completed a strategic planning process that redesigned our college to careers work. This redesign includes a future leadership institute (launching summer 2019) that will allow a select number of existing Chicago Scholars to participate in a year-long experience that will fast track their non-cognitive and leadership skills. We are searching for an innovative leader who will help us successfully launch this inaugural program while at the same time guiding our career and leadership development work for our broader Scholar and alumni community. The ideal candidate will be a strong manager of people and have experience in curriculum design, partnership building and project management.

Key Responsibilities:

Successfully launch and oversee the implementation of our Leadership Institute

o Oversee the selection of inaugural institute Scholars

o Design Leadership Institute curriculum

o Develop relationships with key partners to leverage existing resources and existing curriculum

o Ensure proper marketing, awareness, and interest among Scholar community

o Manage program to ensure 95% retention and completion of the Institute

Manage overall career and leadership program offerings and resources for all Scholars

o In collaboration with the President & CEO and Director of Corporate Giving, identify, build and manage a portfolio of career partners

o Create targeted career exploration events and programs to expose Scholars to potential career options

o Determine (using data) what resources and events will have the greatest impact on Scholar outcomes

Hire, train and oversee Career and Leadership Development staff to execute the following key events and activities:

o Career Exploration events

o First Look: Career Fair

o Chicago Scholars Day

o Annual Scholar Holiday Party

o Career Mentor Program

o Internal Job Board

Create a strategy for maximum alumni engagement

o Manage staff to provide programming and resources to support the needs of our growing alumni network

o Engage with alumni to increase their connection to Chicago Scholars and willingness to reinvest their time, talent, or treasure in Chicago Scholars

o Oversee Alumni Leadership Council, including recruitment and bi-monthly meeting facilitation to grow and support the Chicago Scholars Alumni network

Create a technology strategy that will allow for scale and efficiency of our career and leadership development resources for Scholars

o Redesign our current job board to create a more robust career portal

o Establish a virtual way to connect our Scholars and alumni with “Friends of CS”

o Launch a platform to deliver critical career and leadership development information, resources and workshops virtually rather than in-person (e.g. webinars)

o Assess student needs/requirements and measure learning and impact of virtual resources

Additional Responsibilities worth noting

o This team manages many events that happen in the evening and on weekends. It is important that the VP is present at all events especially in the first year

o VP of Career and Leadership Development will hire and train new team members (e.g. executive coaches) to support the newly developed Leadership Institute

o Work closely with VP of Programs to ensure leadership development is embedded throughout college access and success activities and workshops in a way that builds on the strategic vision for career and leadership development

o Conduct a programmatic audit to determine what activities, resources and events we need and are no longer needed


Education: Undergraduate degree required, Master’s degree preferred

Experience: 10-15 total experience, with 7-10 years of relevant experience including at least five years of managing a team of direct reports. 3-5 years of proven record of success securing and managing corporate support and/or partnerships.


• Exceptional verbal, written and interpersonal skills and ability to engage a broad spectrum of audiences and consistently demonstrate respect, concern, and responsiveness.

• Ability to speak in public and engage all stakeholders (students, parents, mentors, volunteers, college representatives).

• Demonstrated ability to cultivate and sustain relationships with diverse audiences (educational level, socio-economic circumstance).

• Ability to manage projects, organize and compile complex tasks, and prioritize multiple assignments to meet deadlines and objectives.

• Ability to remain flexible and adapt to changing needs and priorities.

• Advanced proficiency with technology and standard office applications and ability to learn and master other computer technology/software programs as needed.

• Ability to think strategically and innovatively to support organizational growth and change.

• Demonstrated ability to interpret data for decision making and program/process evaluation; ability to make recommendations for continuous improvement using data driven approach.

• Demonstrated management skills, including the ability to manage change and generate a culture of continuous improvement.

• Ability to manage a team and a budget to achieve defined goals and demonstrate a commitment to use resources effectively.

• Ability to handle sensitive and confidential information with discretion.

• Business minded and strategic planner

• Self-motivated and self sufficient

Professional Level


Minimum Education Required

4-year degree

How To Apply

To Apply

- Please click 'Apply' to submit your application which should include a resume and cover letter no later than Wednesday, April 3, 2018.

- All candidates MUST be available for a first round group interview the morning of Tuesday, April 10, 2018 

- Chicago Scholars sees a college education as a means to an end with the end game being leadership. In your cover letter, discuss any innovative or creative ways that you think organizations like Chicago Scholars can support first generation students to develop leadership skills that will position them for success beyond college?