Options School Evaluator

Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over 310,000 students in 600+ schools and employing nearly 40,000 people, most of them teachers. CPS has set ambitious goals to ensure that every student, in every school and every neighborhood, has access to a world-class learning experience that prepares each for success in college, career, and civic life. In order to fulfill this mission, we make three commitments to our students, their families, and all Chicagoans: academic progress, financial stability, and integrity.  Six core values are embedded within these commitments – student-centered, whole child, equity, academic excellence, community partnership, and continuous learning.

The Options Network provides administrative support, strategic direction, and leadership development to its schools, mirroring the support model found across the district’s traditional networks. However, the Options Network is unique in its dual-function, serving as both support infrastructure and the authorizing body for a highly diverse portfolio of 36 schools and programs serving approximately 6,000 students. While the network includes traditional district-run schools, 32 of its 36 schools operate as non-district entities (charter, contract, and ALOP models). Consequently, the network’s authorization function demands rigorous, continuous oversight, monitoring, support, and evaluation across three critical pillars: academic performance, financial stability, and operational compliance. 

Job Summary: 

Reporting to the Manager of Options Performance & Support within the Options Network, the Options School Evaluator serves as a key member of the Authorization Team leading and participating in charter, contract, and Alternative Learning Opportunities Program (ALOP) academic renewal evaluations and site visits. This role utilizes CPS-aligned rubrics to collect data, analyze educational practices, and assess instructional quality, school leadership, climate, and academic programming. The role is responsible for synthesizing site visit observations, stakeholder input, and school artifacts into comprehensive, final Site Visit Reports that inform high-stakes accountability decisions and network-wide strategic planning. The Options School Evaluator collaborates with the team to effectively and strategically integrate all deliverables into the renewal and authorization process.

The Options School Evaluator will be held accountable for the following responsibilities:

• Conduct comprehensive site visits using standardized, evidence-based rubrics, focusing on instructional quality, school leadership, climate and culture, and data-informed practices

• Participate in all network site visits, including those focused on academic quality, school culture and climate, and special education, serving as a co-lead evaluator for academic reviews while actively contributing to and supporting the team during all other evaluative components 

• Participate in all site visit components, including school preparation meetings, rigorous classroom observations, artifact/document reviews, and stakeholder focus groups and listening sessions 

• Synthesize complex qualitative and quantitative data collected during site visits and submitted by schools to assess performance, compliance, and readiness for contract renewal

• Author comprehensive Site Visit Reports that provide clear, objective findings and actionable recommendations aligned to renewal standards

• Engage in regular inter-rater reliability exercises and calibration sessions with fellow evaluators and network leaders to ensure consistent and unbiased rubric application across all site visits

• Analyze network-level evaluation data to synthesize systemic trends, isolate instructional gaps, and identify opportunities for macro-level growth across all Options school models  

• Collaborate on the development and execution of the tiered academic support process and other training and workshops for school leadership teams, directors, and network partners as needed

• Serve as a core contributor to Options Network cross-functional teams, ensuring site visit evaluation data and compliance findings actively inform macro-level academic strategy and network-wide resource allocation

• Review and update evaluation rubrics and forms on an ongoing basis to ensure they accurately reflect and respect the unique operational context of Options schools

• Engage actively in district-led professional development and utilize established instructional frameworks to continuously refine classroom observation lenses, maintain mastery of rigorous pedagogical practices, and standardize evidence-gathering techniques. 

• Partner with fellow team members to establish the annual calendar, workflows, and operational cadence for school preparation, site visit execution, and report generation  

• Other duties as assigned  

In order to be successful and achieve the above responsibilities, the Options School Evaluator must possess the following qualifications: 

Education Required: 

• Bachelor's degree in Education or a related field from an accredited college or university

• Valid teaching certificate/Professional Educator’s License (PEL) issued by the Illinois State Board of Education (ISBE) with an endorsement in Math, Science, Literacy or Social Sciences, required

• Master’s degree, preferred

• Valid Administrative Endorsement / PK–12 Principal Endorsement, preferred

• ISBE Teacher Evaluator Qualifications, preferred

Experience Required: 

• Minimum of five (5) years of classroom teaching experience, required

• Minimum of three (3) years of teacher leader or school leadership experience, preferred

Additional Requirements

• Must have access to reliable transportation, as frequent travel to schools across the city is required to conduct site visits and provide on-site support

Knowledge, Skills and Abilities: 

• Possess deep understanding of research-based evaluation frameworks, universal design for learning (UDL), adult learning theories, and evidence-gathering techniques to assess school performance 

• Ability to effectively evaluate school leadership, climate, and instructional quality across varied programs, including those serving Diverse Learners, English Learners, and over-age/under-credited youth

• Ability to analyze and translate complex qualitative and quantitative evaluation data into valid conclusions and systemic trends, and inform strategic action plans

• Strong writing skills to generate comprehensive, objective site visit reports containing actionable school improvement recommendations

• Ability to exercise high levels of professional credibility and the courage to make difficult, evidence-based school accountability decisions

• Ability to design and deliver effective professional development, targeted workshops, and strategic coaching for adult learners and school leaders

• Collaborate effectively within an integrated evaluation team structure and across cross-functional networks

• Ability to utilize strong verbal communication, presentation, and listening skills to build trust and transparency with diverse school communities

• Ability to maintain a foundational knowledge of school operations, continuous improvement cycles, management, and organizational development

Conditions of Employment

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

• Establish/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.