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Chief of Staff

Chicago - Illinois (IL), 60603

City Year

Job Description:

Reporting to the Vice President and Executive Director of City Year Chicago, the Chief of Staff oversees the activities of the Executive Office, administrative operations, and human potential operations, and advances City Year Chicago’s agenda. The selected candidate will assist the Executive Director with strategic priorities, and prioritize and monitor tasks related to the execution and implementation of a broad agenda.

The Chief of Staff serves as a trusted senior advisor to the Executive Director and acts in his/her place, as appropriate, including representing him/her in high level meetings and discussions. He/she will provide oversight on time sensitive issues and initiatives that include cross-functional, organizational, partnership and community dimensions. They are also responsible for building and sustaining an effective support structure for the site’s senior leadership team.

Job Description

Site Strategy and Special Initiatives (20%)

  • Manage the process for implementation, review, and modification of City Year Chicago’s strategic plan (Long Term Impact Blueprint) to ensure departmental and site-wide progress is met and remains aligned with staff capacity, financial resources, and stakeholder support.
  • Support the development of City Year Chicago’s high priority goals and assist departments with the development of their annual operation plans.
  • Monitor departmental and individual progress towards annual goals, recommend action, and advise Executive Director concerning interventions as necessary.

Board Management (10%)

  • Support the Executive Director and Special Projects Director with managing preparation for meetings, retreats, and communications of the City Year Chicago Board.
  • Represent the VP/Executive Director with board relations and engagement as needed.
  • Oversee the preparation for board meeting including documents, presentations and other collateral materials.

Executive Office Management and Site Operations (30%)

  • Prioritize agenda and schedule of the Executive Director and manage work flow of the Executive Office and Senior Leadership Team (SLT).
  • Oversee the performance management process and ensure staff members complete in a timely manner the performance management procedures and support them in reaching their individual development plan goals.
  • Oversee and support site efforts and the People Team in ensuring high staff retention and recruiting highly qualified staff members to the team as appropriate.
  • Review correspondence on behalf of the Executive Director to ensure communication is accurate, timely, and coordinated with other City Year Chicago and City Year Inc. initiatives.
  • Foster productive and collaborative relationships internally and externally on behalf of the Executive Director and Senior Staff Team.
  • Establish and communicate site-wide processes and policies on behalf of City Year Chicago and in consultation with City Year Inc.
  • Manage a broad range of internal and external relationships and execute follow-up and responses as necessary.
  • Gain a strong understanding of City Year policies and procedures necessary to ensure appropriate decision-making protocols are followed.

Budget Development and Financial Monitoring (20%)

  • Oversee and support the site in the annual budget development process in consultation with Executive Director, MD Pops and Headquarters staff.
  • Lead the site through site operation planning and advise on opportunities to maximize financial and operational efficiencies.

Organization Initiatives (20%)

  • Partner on cross-department projects and initiatives including but not limited to the AmeriCorps member selection process, stakeholder engagement, service day participation and cross-departmental committees as needed to ensure site-wide goals are met.
  • Attend and support whole site events including Opening Day, Make A Difference Day, MLK Day, Global Youth Service Day, Annual Gala, Graduation, and other site-wide designated events.
  • Assume other tasks as delegated by Executive Director


  • Bachelor’s degree required and Master’s Degree highly preferred
  • At least 8 years of team management/leadership experience required with a proven track record of success
  • Excellent organizational skills, ability to problem solve and think critically
  • Results-focused, highly organized self-starter who works effectively with others and independently
  • Excellent strategic planning and project management skills
  • Ability to confidently manage a high-volume, deadline-driven workload with poise and optimism
  • Experience with navigating a complex political landscape and developing relationships with key stakeholders
  • Demonstrated ability to lead manager and directors in creation and implementation of multi-faceted operating plans
  • Demonstrative social and emotional intelligence

Deep understanding of and commitment to City Year’s values, for more information visit:

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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