Jun 27, 2019

Vice President, Executive Director

  • City Year
  • Chicago, IL, USA
Full-time Executive Leadership

Job Description

City Year is seeking an innovative, entrepreneurial, and people-focused leader to serve as the Executive Director (ED) at City Year Chicago. This position is an outstanding opportunity to play an integral role in advocating for and advancing public education in Chicago. This seasoned executive is responsible for ensuring the Chicago site meets its impact, revenue, district partnership, and external relations goals. City Year Chicago stands to further its position in the Chicago community, and key to the site’s success is a leader and collaborator who is a natural coalition-builder, people developer, and influencer who leads with both tenacity and humility.

Reporting to the Regional Vice President of the Midwest Region, this dynamic, visionary change agent leads 54 staff members and 254 AmeriCorps members serving in 30 partner schools. Additionally, the Executive Director works closely with City Year Chicago’s local advisory board, comprised of leaders in the public, private, and non-profit sectors of Chicago. The Executive Director is accountable for a current annual budget of approximately $12M (current make up is 57% public sector including school district and AmeriCorps and 43% private sector) while simultaneously securing the resources necessary to ensure the sustainability, growth, and scale to achieve City Year’s national Long-Term Impact goals.

Serving as the primary champion of City Year’s impact locally, the Executive Director leads efforts to keep students in school and on track, while also ensuring the sustainability and continuity of the site. The Executive Director represents the organization within the Chicago community by mobilizing powerful coalitions to catalyze greater educational opportunity for underserved students. These constituencies include advisory board members; district leadership and school partners; Serve Illinois; alumni; and private sector investors.

Additionally, the Executive Director is a Vice President for City Year Inc.’s national organization and therefore strengthens the connection between City Year’s national initiatives and the local work in Chicago. Through this role as Vice President, the Executive Director also participates within the City Year global network to advance the mission by managing working relationships with staff at City Year’s national office and helping to lead and set organizational strategy through network-wide project teams.


The Executive Director is responsible for leading and managing site staff and AmeriCorps members to ensure operational success and growth by generating resources and building support from the public and private sectors. This executive serves as a vital link between the local Chicago market, the City Year Midwest Region, and the City Year national office. Site supervision includes the functional areas of student impact and school partnerships, revenue generation, expense management, management and retention of AmeriCorps members and staff, and site board development and relations. 

Our Executive Directors embody our core values and must have the firm belief that education has the power to help all students reach their full potential and a passion for increasing our nation’s graduation rates. To successfully execute the job’s core responsibilities, a successful Executive Director must demonstrate the following behaviors: 

  • Build and forge partnerships and coalitions with diverse stakeholders to advance the cause of educational equity 

  • Mobilize internal and external stakeholders towards a bold vision of how they can impact the lives of young people  

  • Build and empower teams to fully own their functions while driving accountability and take personal responsibility for their success  

  • Build community and foster a caring and supportive environment with sense of connection and belonging 

  • Demonstrate curiosity and humility as a life-long learner who seeks out diverse perspectives and opportunities for self-improvement 

  • Possess a deep sense of personal accountability to ensure the success of both City Year Chicago locally and City Year, Inc. nationally 

  • Connect with and inspire diverse teams of AmeriCorps Members between the ages of 18 and 25 


Through these lenses, the Executive Director will focus on the following primary areas of responsibility: 

People and Culture: Lead, coach, and develop 54 full-time staff members, increase staff engagement (70% or greater) and retention of staff year over year (staff turnover 25% or less). Establish a dynamic culture that embodies our core values of inclusivity and teamwork. Further develop site human resources structures to ensure equitable hiring and promotion practices. 

AmeriCorps Member Experience: Ensure the site delivers a transformational experience for all City Year AmeriCorps members, where at least 93 percent of AmeriCorps members persist from confirmation to completion of service and 80% of AmeriCorps members report feeling prepared and confident in their service delivery.  

Student Impact: In partnership with senior site staff and regional support staff, the ED will ensure high quality and commitment to the nationally developed service delivery model implemented by City Year AmeriCorps members in partner elementary, middle, and high schools.   

Private Sector Fundraising, Cultivation, and Stewardship: Serve as chief fundraiser and lead site staff and local advisory board to motivate key influencers to raise the funds necessary to meet annual and long-term revenue goals by leveraging national revenue and stewardship strategies. Develop a plan to increase private sector revenue in order to keep pace with public sector revenue (goal is 50/50.)  Identify, cultivate, solicit, and manage strategic relationships with corporations, foundations, family foundations and individuals in order to build a sustainable private revenue mix that results in annual revenue of at least $5M. 

School/District Investments: Sustain transformational partnerships with existing district and school leadership and cultivate new transformational partnerships with leaders of future school partners. Negotiate contracts that result in sustained annual revenue of at least $3M 

Financial Management: Ensure City Year Chicago raises three percent more than it spends annually by managing fiscally-sound budget, forecasting, expense management, and cash flow for a current site budget of $12M. 

Board Member Engagement: Recruit, develop, and manage a diverse, dynamic and deeply engaged local advisory board to build and execute a multi-year site strategic plan focused on local fundraising efforts, community engagement and brand awareness while also contributing to the success of the national organization. Ensure cultivation and engagement of future board leadership.  

Government Relations and Public Policy: Engage local and national elected officials – Governor, Mayor, City Council, local and state school board representatives, Illinois State Legislature, and members of U.S. Congress - to support funding and policies for City Year and the national service movement. Maintain effective and collaborative relationship with AmeriCorps state commission Serve Illinois; oversee the preparation of effective AmeriCorps grant applications and progress reports and meet performance and compliance requirements associated therein. 

AmeriCorps Member Recruitment: Collaborate with City Year’s national recruitment and admissions team to ensure site recruits, selects, and admits AmeriCorps members within the regional framework, meeting quality, quantity, and inclusivity goals. Partner with site staff to ensure a strong cohort returns annually for a second year of service, with at least 40% of first year members applying for a second year of service.  

Alumni Engagement: Ensure the development of local alumni board to leverage alumni to support AmeriCorps members in service and continue their lifetime of service. 

Marketing and Communications:  Lead the site in increasing visibility and brand awareness of City Year’s work in local and national media, social media and marketing channels by developing and leveraging local relationships.  


In Chicago, the top priorities include:  

  • Ensuring financial solvency of City Year Chicago by growing the current community of champions and financial investors to meet existing revenue goals and ensure future expansion into Chicago area schools.  

  • Leading local site board and recruiting diverse talent to the board to support future financial sustainability and growth while increasing brand awareness and recognition of City Year in the local community.  

  • Further advance the site’s commitment to diversity, equity, inclusivity and belonging by investing in people, culture, community, and partnerships while prioritizing inclusive and equitable systems, processes, and practices. 

  • Deepening public sector relationships with emphasis on the City of Chicago and the Chicago Board of Education and establish relationships with key members of the administration, city council and school board. 


  • Strong ability and experience in the behaviors listed above 

  • Strong competency in diversity, equity, inclusion, and belonging work; emotional intelligence, and experience and comfort working with underserved communities 

  • Demonstrated success managing effective and engaged teams, including managing through multiple layers of leadership  

  • Proven skills in influencing and motivating stakeholders; track record in fundraising from corporations, foundations and major gifts and/or sales  

  • Ability to connect programs to funding, creatively generating other resources, and building collaborative and strategic partnerships 

  • Strong communication, listening, and public speaking skills needed to powerfully represent City Year’s mission and vision  

  • Ability to attend evening and weekend events; ability to travel to in-person meetings in various cities quarterly  

  • Significant local non-profit, volunteer, or multi-sector experience preferred 

  • An established cross-sector, local network a plus 

  • Knowledge of Chicago and Chicago educational landscape preferred 

  • Content knowledge of K-12 education, youth development, and/or community or national service a strong plus 


Deadline to apply is Monday, July 15; applications accepted on a rolling basis after this date.  Please submit your cover letter and resume via the online application. 

Compensation and Benefits

Full time employees are entitled to compensation commensurate with experience. Benefits for full time employees include health insurance with Flexible Spending Account, paid vacation, holidays, parental leave, 401K, and more.

City Year is an Equal Opportunity Employer, committed to a diverse workforce. Individuals from all backgrounds are encouraged to apply, including persons with disabilities and veterans.

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