Options School Evaluator

About the Role

The Options School Evaluator serves as a key member of the Authorization Team within the Options Network at Chicago Public Schools (CPS), leading and participating in academic renewal evaluations and site visits for charter, contract, and Alternative Learning Opportunities Program (ALOP) schools. This role utilizes CPS-aligned rubrics to assess instructional quality, school leadership, climate, and academic programming, synthesizing observations and data into comprehensive Site Visit Reports that inform high-stakes accountability decisions and network-wide strategic planning.

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 academic quality, school culture and climate, and special education, serving as a co-lead evaluator for academic reviews.
• Engage in all site visit components, including school preparation meetings, classroom observations, artifact/document reviews, and stakeholder focus groups and listening sessions.
• Synthesize complex qualitative and quantitative data to assess performance, compliance, and readiness for contract renewal.
• Author comprehensive Site Visit Reports with clear, objective findings and actionable recommendations aligned to renewal standards.
• Participate in inter-rater reliability exercises and calibration sessions to ensure consistent and unbiased rubric application.
• Analyze network-level evaluation data to identify systemic trends, instructional gaps, and opportunities for growth across Options school models.
• Collaborate on the development and execution of tiered academic support processes, training, and workshops for school leadership teams and network partners.
• Contribute to cross-functional teams, ensuring evaluation data informs macro-level academic strategy and resource allocation.
• Review and update evaluation rubrics and forms to reflect the unique operational context of Options schools.
• Engage in district-led professional development to refine classroom observation techniques and maintain mastery of pedagogical practices.
• Partner with team members to establish the annual calendar, workflows, and operational cadence for site visits and report generation.
• Perform other duties as assigned.

Requirements

• 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.
• Minimum of five (5) years of classroom teaching experience.
• Access to reliable transportation for frequent travel to schools across Chicago.

Qualifications (Preferred)

• Master’s degree.
• Valid Administrative Endorsement / PK–12 Principal Endorsement.
• ISBE Teacher Evaluator Qualifications.
• Minimum of three (3) years of teacher leader or school leadership experience.

Skills

• Deep understanding of research-based evaluation frameworks, universal design for learning (UDL), adult learning theories, and evidence-gathering techniques.
• Ability to evaluate school leadership, climate, and instructional quality across diverse programs, including those serving Diverse Learners, English Learners, and over-age/under-credited youth.
• Strong analytical skills to translate complex qualitative and quantitative data into actionable insights and systemic trends.
• Excellent writing skills to produce comprehensive, objective site visit reports with actionable recommendations.
• High professional credibility and courage to make evidence-based accountability decisions.
• Ability to design and deliver effective professional development, workshops, and strategic coaching for adult learners and school leaders.
• Collaborative skills to work within an integrated evaluation team and across cross-functional networks.
• Strong verbal communication, presentation, and listening skills to build trust with diverse school communities.
• Foundational knowledge of school operations, continuous improvement cycles, management, and organizational development.

Conditions of Employment

Employees must establish and maintain Chicago residency within six months of their hire date and throughout their employment with CPS. This requirement does not apply to temporary/part-time positions, though all employees must be Illinois residents.