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Senior Service Director

City Year · Chicago, IL · $90,000–$100,000 a year · Full time

Posted Aug 27, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you designed and rolled out a program model across many sites or schools.

What they are checking: Whether they can implement a model like Whole School Whole Child consistently at scale.

How do you develop the managers who report to you?

What they are checking: Whether they build leaders, which decides whether the department can grow and sustain impact.

Tell me about a time you had to make a hard call that affected a team you cared about.

What they are checking: Whether they make difficult decisions with fairness and clear communication.

How do you keep your department's work tied to the Managing Director of Impact's priorities?

What they are checking: Whether they manage up well and stay aligned with the broader Impact Department.

What would you do

How would you set a vision for a Service Department that includes Learning and Development and Instructional Coaches?

What they are checking: Whether they can shape a department's direction and connect each team's work to student outcomes.

A CPS principal is unhappy with how the City Year team is working in their school. How do you respond?

What they are checking: Whether they can protect a key partnership by listening and making real changes.

How would you balance quality of service with pressure to scale to more schools?

What they are checking: Whether they can weigh growth against impact and sustainability, as the role requires.

AmeriCorps members are young and serving for ten months. How do you keep them engaged through the hard winter months?

What they are checking: Whether they understand corps retention and support, which affects grant terms and school results.

About the work

You are the main contact for the AmeriCorps grant. How do you make sure the site stays compliant?

What they are checking: Whether they understand federal grant requirements like member hours, documentation and reporting.

What data would you use to judge whether the service model is working?

What they are checking: Whether they rely on attendance, behavior and course performance data instead of anecdotes.

Practice this interview out loud.

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The full job description

As published by City Year.

Application Instructions 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: Hybrid On-Site/Remote Position Overview The Senior Service Director (SSD) will report directly to the Managing Director of Impact and holds an integral role within the leadership and functions of the Impact Department at City Year Chicago. The SSD serves as the primary leader for the Service Department, working to set the vision and functions of this team which includes Learning and Development and Instructional Coaches.  The role of the Senior Service Director is critical towards the design and implementation of the Whole School Whole Child (WSWC) service model across our partnered Chicagoland Schools. The Senior Service Director is accountable for the department’s strategy, performance, and success in achieving its potential for impact, sustainability, and scale. As a leader in the Impact Department, the Senior Service Director will act as the main contact for the AmeriCorps Grant and manage this critical part of our organization. This role also plays a role in developing, managing, and improving relationships with (CPS) and all other Chicagoland schools with the Managing Director, Impact (MDI). Salary Range for this role is $90,000 to $100,000 Anticipated start date is Fall 2026 The SSD will primarily work at the office with occasional visits to partner schools. Job Description Minimum Qualifications • Bachelor's degree, plus 8+ years of experience working in K-12 school systems working in education, program evaluation and management, or adult learning fields, preferably within CPS and/or Chicagoland area • Knowledge of adult learning principles and experience in implementing these principles • Knowledge of program evaluation and implementation on a large scale • Experience in analyzing large data sets to draw conclusions and create solutions. Responsibilities The Senior Service Director   will perform the following roles and responsibilities as described below: Program Design, Implementation and Evaluation • Manage the development and execution of City Year Chicago’s service model implementation to ensure  that the implementation plan remains aligned with capacity, organizational and community stakeholder support and organizational priorities. (School partnerships, student engagement, academic support, and student progress monitoring) • Ensure service quality and attainment of City Year Chicago’s impact goals through observations and evaluation of in-school services for staff and AmeriCorps members • Support the collaboration between the Service Team and the Impact Department to ensure that all AmeriCorps members are adequately prepared to deliver high quality interventions to students. • Lead site on identification, implementation, and execution of instructional and student-centered pilots, when applicable • Ensure appropriate data has been sourced, collected, and analyzed in order to evaluate the program model and implementation, through the analytics department. Service Department Leadership & People Management • Lead and provide vision, strategy, and oversight for the Impact Service Department • Work with and manage the Senior Manager of L&D, as well as instructional coaches to ensure that the WSWC model is functioning as intended and the ACMs are prepared to enact the model, infusing feedback and utilizing evaluative data when necessary • Effectively manage, mentor, and develop the Senior Manager • Effectively manage the instructional coaching team in order to provide the staff and AmeriCorps members with timely , relevant trainings and support to meet student outcomes, support school priorities and service delivery goals • Effectively works alongside the Director of Analytics who works closely with a shared Analytics manager from CYHQ, in order to appropriately build systems to progress monitor service model efforts, student outcomes, service goals and etc. as well as evaluate our program model. • Design, implement and progress monitor towards an effective coaching and L&D model which supports ACMs instructional development and enhance student outcomes as well as help to development impact staff towards sound instructional practices and protocols • Effectively hire and determine relevant and appropriate onboarding into the department and organization for all incoming team members • Work alongside department leadership to perform other necessary duties as assigned Partnerships • Work with MDI to build upon and foster new relationships within CPS and beyond to ensure needs of partnerships and CY are both being met • Collaborate with service partners to ensure service model complements school climate, culture, and instructional priorities of our partners • Serve as the site AmeriCorps point person, act a liaison between local site and HQ • Liase with CPS and external stakeholders to ensure our impact is elevated and appropriately narrated through our data, evaluations and implementations. Organizational Initiatives & Site Leadership • Establish operating policies and procedures along with the MDI within the Impact and Service Department that are consistent with the organization’s mission and culture. • Communicate and collaborate with key staff at City Year Headquarters, Market B Impact leadership and Managing Directors of Impact and National Learning and Development department and other City Year sites around model fidelity, best practices, assessments, pilots, resources, feedback, strategic partnerships, data and analytics • Complete all grant reporting for CYCHI AmeriCorps grants and monitor compliance and progress towards goal • Serve as the AmeriCorps point person for the site; liaise between the Serve Illinois Commission, the local site and City Year Headquarters (CYHQ), • Collaborate with the Senior Director, Site Operations to monitor grant compliance in regard to background checks, registration and other various requirements • Work alongside the Senior Director Team in order to effectively lead out on Impact Staff and village spaces to drive organizational goal and priorities as well as foster a sense of community and belonging across the departments • Actively participate in all site and HQ staff meetings (network gatherings, site staff meetings, department meetings, site leadership team meetings, etc.) Benefits 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.

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