Senior Service Director

City Year; Chicago (IL); On-site; USD 90,000 - 100,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

401(k) plan

Paid time off and holidays

Job summary

City Year Chicago seeks a Senior Service Director to lead the Impact and Service Department, including Learning & Development and Instructional Coaches. You will drive the WSCC service model, oversee AmeriCorps partnerships, and ensure program effectiveness across partnered schools with a focus on sustainability and scale.

The role requires a Bachelor’s degree with 8+ years in education or related fields, strong data analysis, and program evaluation experience.

Qualifications

• Bachelor's degree plus 8+ years of experience in K-12 education, program evaluation and management, or adult learning fields.
• Knowledge of adult learning principles and experience applying them.
• Experience evaluating programs at scale and analyzing large data sets.

Responsibilities

• Design, implement, and evaluate City Year Chicago’s service model to align with capacity and community priorities.
• Oversee quality of in‑school services and ensure impact goals are met.
• Lead L&D and instructional coaching to support the WSCC model.
• Mentor and develop Senior Manager and coaching staff for effective instructional practices.
• Collaborate with analytics to monitor progress and outcomes.

Skills

Adult learning principles

Program evaluation

Data analysis

Large data sets analysis

Education

Bachelor's degree + 8+ years experience in K-12 education

Job description

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 Directorwill 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.


• Employment at City Year is at-will. City Year does not sponsor work authorization visas.

As an equal opportunity employer, City Year is committed to providing employment opportunities to all qualified individuals and does not discriminate on the basis of race, color, ethnicity, religion, sex, gender, gender identity and expression, sexual orientation, national origin, disability, age, marital status, veteran status, pregnancy, parental status, genetic information or characteristics, or any other basis prohibited by applicable law.

Fair Labor Standards Act Family and Medical Leave Act Learn more at www.cityyear.org, City Year’s Facebook page, on X (formerly Twitter), and LinkedIn.