
Click Apply to submit your online application. Please attach a resume and thoughtful cover letter on the "My Experience" page in the "Resume/CV" field.
Active City Year Staff members must login to Workday to apply internally.
Number of Positions: 1
Work Location: 100% On-Site
Reporting to the Senior Vice President & Executive Director, the Managing Director of External Affairs & Engagement is responsible for advancing City Year Chicago's visibility, influence, strategic partnerships, and stakeholder engagement efforts. As a member of the Executive Leadership Team, this leader will oversee external affairs functions including communications, marketing, media relations, government affairs, strategic partnerships, and signature events.
The Managing Director serves as a primary ambassador for City Year Chicago, building meaningful relationships with civic, business, community, philanthropic, and government leaders while elevating awareness of the organization's impact. This role is responsible for expanding City Year Chicago's presence, strengthening engagement with key stakeholders, and leveraging external relationships to advance organizational priorities and mission outcomes.
-Starting salary range for this role is $135K to $145K .
-Anticipated start date for this role is fall 2026.
-This is a primarily in-person role with flexibility to periodically work remotely.
External Affairs Strategy & Stakeholder Engagement
Communications, Marketing & Brand Management
Government & Community Affairs
Signature Events & Strategic Engagement
Organizational Leadership
A cover letter and resume must be submitted to be considered for this position. Preferred resume formats will depict not only a candidate’s responsibilities and job functions in previous work, but will include specific, quantitative results where applicable. Additional quantitative context around specific budget sizes, team sizes, or other work environment information will help City Year compare the scale of your work environment with our operations.
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.
Full-time employees will be eligible for all benefits including vacation, sick days and organization holidays. You may participate in all benefit programs that City Year establishes and makes available to eligible employees, under (and subject to all provisions of) the plan documents that govern those programs. Currently, City Year offers medical, dental, vision, life, accidental death and dismemberment and disability coverage, Flexible Spending Accounts (FSA), and other benefits including 401(k) plan(s) pursuant to the terms and conditions of company policy and the 401(k) plan document. For more information, click here.
Employment at City Year is at-will.
City Year does not sponsor work authorization visas.

City Year helps students and schools succeed, while preparing the next generation of leaders. City Year AmeriCorps members provide support to students, classrooms and the whole school. Schools that partner with City Year are up to two to three times more likely to improve in English and math assessments, and the more time students spend with AmeriCorps members, the more they improve on skills that help students thrive in school and contribute to their community.
A proud member of the AmeriCorps national service network, City Year is supported by AmeriCorps, local school districts and private philanthropy. City Year partners with public schools in 29 communities across the U.S. and through international affiliates in the U.K. and South Africa.