Executive Director, Assessment & MTSS

Job Summary Reporting to the Deputy Chief of Teaching & Learning, the Executive Director, Assessment & MTSS provides strategic vision, leadership, and administrative oversight for the district's comprehensive assessment and multi-tiered system of supports (MTSS) intervention frameworks. This role leads a high-performing department responsible for the policy, design, implementation logistics, data infrastructure, and continuous improvement of all large-scale, enrollment-based, curriculum-embedded, and teacher-evaluation assessments, as well as equity-based MTSS implementations across the district. The Executive Director ensures assessment and MTSS systems are valid, reliable, accessible, instructionally meaningful, and used appropriately to inform decisions about student learning, instructional improvement, program quality, and equitable access to supports. By fostering cross-functional collaboration and managing critical relationships with state, union, vendor, and community partners, the Executive Director ensures that students across all networks have equitable access to high-quality assessment systems and coherent, evidence-based supports aligned with a rigorous, standards-aligned instructional experience. This is a full-time, exempt position paid on a salary basis for time worked.

Responsibilities

Supervises, develops, and manages the performance of a team responsible for large-scale assessments, access and enrollment testing, curriculum-embedded assessments (Skyline), REACH performance tasks, data strategy, and MTSS frameworks.

Guides the department's long-term strategic plans, data inquiry cycles, and Continuous Improvement Plans to optimize operational efficiency and maximize positive impacts on student learning with an explicit lens for equity, access, and inclusion.

Spearheads district-wide policy development and standardization for the high-fidelity design, secure administration, implementation, and evaluation of all balanced assessment systems across the Pre-K through 12 grade continuum.

Oversees the strategic expansion, implementation, and continuous improvement of the district's equity-based MTSS framework as an integrated academic, behavioral, social-emotional, and attendance support system grounded in strong Tier 1 instruction, universal screening, progress monitoring, evidence-based interventions, and clear decision-making protocols.

Facilitates critical partnerships across Central Office departments to align assessment implementation, data reporting, and teacher evaluation integrations with broader district priorities; advises the Law Department and other executive leadership on high-stakes assessment vulnerabilities, test security violations, and regulatory compliance metrics.

Serves as the primary representative and liaison for Chicago Public Schools with the Illinois State Board of Education (ISBE), the Chicago Teachers Union (CTU) Joint Committee on Teacher Evaluation, and national assessment policy convenings.

Leads the procurement, contract management, and performance evaluation of all major third-party testing providers, assessment system vendors, and MTSS platform partners.

Directs the creation and execution of comprehensive, adult learning plans focused on assessment literacy, including assessment purpose, validity, accessibility, accommodations, data interpretation, limitations of use, and translation of evidence into instructional and intervention decisions for network teams, school administrators, and instructional staff.

Champions the structural integrity, cleaning, reporting, and visualization of district performance and growth data, working in concert with enterprise data and research teams to drive critical educational decisions.

Maintains a coherent district assessment strategy by evaluating assessment quality, redundancy, burden, accessibility, alignment to standards and curriculum, and usefulness for instructional decision-making.

Other duties and workstreams as assigned.

Education Required

Bachelor's degree from an accredited college or university with a focus in education, educational measurement/assessment, public policy, or a related field is required.

Master's degree is preferred.

Professional Educator License with an administrative endorsement is required.

Experience Required

Minimum of eight (8) years of progressively responsible experience in assessment, MTSS, accountability, research and evaluation, data strategy, instructional improvement, school support, or a related educational leadership function, including experience using student outcome data to inform decisions at the school, network, district, or system level.

Minimum of five (5) years of experience directly supervising a team of professionals within an educational environment.

Knowledge, Skills, and Abilities

Expert-level knowledge of balanced assessment systems, educational measurement principles, psychometrics, and multi-tiered intervention strategies.

Knowledge of accessibility, accommodations, universal design principles, and appropriate assessment practices for diverse learners, including multilingual learners and students with disabilities.

Deep familiarity with Illinois State Board of Education (ISBE) regulations, federal compliance standards, and Chicago Public Schools assessment and teacher evaluation policies.

Exceptional executive-level project management and strategic planning capabilities; ability to define complex systemic problems, analyse diverse data tracks, and execute valid district-wide action steps.

Outstanding verbal and written communication skills, with a proven ability to articulate a clear educational vision and communicate technical data methodologies to non-technical audiences, executive leadership, policymakers, and community stakeholders.

Strong collaborative relationship-building skills, with the ability to navigate cross-departmental frameworks, negotiate consensus, and manage high-stakes disputes effectively.

Extensive understanding of enterprise data systems, educational technology platforms, data governance principles, and analytics software.

Deep professional alignment with the CPS Instructional Core Vision, showing a relentless career commitment to educational access, equity, and continuous organizational learning.

Conditions of Employment As a condition of employment with the Chicago Public Schools (CPS), employees are required to:

Establish and maintain Chicago residency—Employees are required to live within the geographic boundaries of the City of Chicago within six months of their CPS hire date and maintain residency throughout their employment with the district. The Chicago residency requirement does not apply to temporary/part-time positions; however, all CPS employees must be residents of Illinois.

Salary and Position Type Estimated Annual Salary Range: 130,000.00 – 156,000.00

Position Type: Non-Union Position

Salary Grade: S11

Final Salary Offers Final salary offers are dependent upon candidate qualifications.

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