Chief Schools Officer

KIPP • Chicago, IL

15d

About The Position

The Chief Schools Officer (CSO) is a new role for KIPP Chicago Public Schools and comes at a pivotal moment in the organization’s history. By bringing unified oversight to our K–through–postsecondary continuum and ensuring excellence is consistent across every school, creating a Chief Schools Officer role represents an important evolution in how we organize our executive leadership. The Chief Schools Officer will lead the Schools Team, with a focus on development, alignment, and excellence across our schools, alumni support, and programs. The Chief Schools Officer will bring a sharper focus to instructional leadership, deepen principal development, and strengthen alignment across all schools so that excellence is not isolated, but aligned and systemic.
Reporting to the Chief Executive Officer and serving on the Executive Leadership Team, the Chief Schools Officer is ultimately accountable for the outstanding performance of all eight KIPP Chicago schools. The CSO will lead the reorganized Schools Team and will directly manage Principal Managers, the Chief Program Officer, and the Chief of Postsecondary Success ensuring strong coordination, leader development, and performance across the full K-through-postsecondary continuum that supports students from early learning through college persistence. The Chief Schools Officer will collaborate closely with the Executive Leadership Team to ensure strong execution of KIPP Chicago’s academic, talent, and operations strategy across all campuses.
The ideal Chief Schools Officer is a senior, results-driven leader who feels deep personal accountability for delivering strong outcomes for students. They are a systems builder who translates vision into disciplined execution, brings coherence to complex organizations, and ensures that strategy results in measurable impact across schools. The Chief Schools Officer also has deep knowledge of various stakeholder considerations and compliance requirements of K-8 schools in Chicago; if not already familiar with Chicago, they have prior experience in other CMO or district settings and an urgent willingness to learn. Grounded in a deep commitment to equity, the CSO leads with urgency and high expectations, develops leaders to excel as instructional stewards, and holds themselves and others accountable for creating rigorous, affirming, and joyful learning environments where every student thrives.

Requirements

• 10+ years of educational leadership experience, with recent demonstrated success in systems-level leadership (e.g., Principal Manager, Regional Superintendent, Managing Director of Academics or Principal Development), including successful coaching and development of School Leaders
• Minimum of 4 years of experience as a high-performing Principal or school-based instructional leader, with a demonstrated track record of strong student achievement and school culture outcomes
• Demonstrated ability to set and drive a clear, compelling vision with measurable results across multiple schools or teams, preferably in an urban charter school setting
• Proven strengths in systems-level leadership, including designing, aligning, and operationalizing strategy to drive consistent execution and performance
• Commitment to building relationships and trust with leaders, teachers, students, parents, and the community of Chicago
• Track record of advancing equitable outcomes for all student groups, including students of color, multilingual learners, and students receiving special education services
• Exceptional leadership and people management skills, including the ability to build trust, set clear priorities, and hold high standards for effective performance
• Strong collaboration skills, with demonstrated success partnering across academics, talent, operations, and student support functions
• Accurate and well-versed knowledge of school law (Title IX, ADA) and reporting structures in Chicago and Illinois
• Deep commitment to KIPP Chicago’s vision of joyful, academically excellent schools and demonstrated alignment with the organization’s values of perseverance, character development, scholarship, leadership, and collective responsibility in service of students and community

Responsibilities

• Set and lead a clear, shared vision for school excellence across KIPP Chicago
• Establish and drive an ambitious and inspirational vision for school health across the region, spanning the full K-through-postsecondary continuum, that sets a high bar for academic achievement, instructional quality, school culture and operational effectiveness
• Deeply understand and internalize school health metrics as defined by various stakeholders (Chicago Public Schools, Illinois State Board of Education, KIPP Foundation)
• Operationalize the vision by establishing clear goals, defining the leadership behaviors and practices required for success, and leading data-informed continuous improvement cycles to refine strategy and accelerate outcomes
• Effectively lead programmatic and change initiatives to ensure teachers, instructional staff, and school leaders are aligned to and invested in the school quality vision
• Set and uphold clear performance standards across schools, using data to monitor progress, provide differentiated support, and intervene decisively to ensure consistent, high-quality outcomes throughout the region
• With Chief of Programs, align and oversee Whole Child initiatives to ensure students receive the academic, social-emotional, and wraparound supports necessary to thrive
• With Chief of Postsecondary Success, align and oversee KIPP Forward initiatives to ensure students receive the high school and post-secondary supports that promote persistence and success
• Cultivate and sustain learning environments and student supports where students feel supported, engaged, and valued
• Architect and steward a clear regional vision for school culture and student experience, establishing the standards, systems, and leadership practices that enable every school to cultivate safe, joyful, affirming, and academically excellent learning environments
• Develop and equip Principals and Principal Managers to lead culture effectively, translating the regional vision into consistent practices in student behavior systems, adult culture, and family engagement
• Partner with the Academics and Programs Teams to ensure alignment between academics, student supports, and family engagement, to ensure that all students receive the instructional and student support services needed to thrive
• Oversee the effective implementation and impact of social-emotional learning initiatives active in schools
• Assess and lead efforts to improve the role clarity and impact of positions that support school culture (Peer Leaders, Student Engagement Chairs, Assistant Principals, School Operations and School Leaders)
• Serve as KIPP Chicago’s final point of contact for high stakes student and parent/guardian needs
• Build and lead a high-performing Schools Team (inclusive of Principal Managers and all Principals) focused on achieving strong, equitable academic and culture outcomes across all schools
• Lead, coach, and develop the regional and school leaders to deliver measurable gains in student achievement, academic growth, attendance, and school climate, while reducing performance gaps across student subgroups and variability across schools
• Ensure all schools meet or exceed regional academic targets, including demonstrated gains in proficiency and growth across state, interim, and formative assessments
• Co-design and facilitate the Principal Learning Community that builds principals’ leadership capacity, fosters trust and collaboration across schools, and aligns leaders around a shared vision to improve student outcomes
• Provide strategic guidance and differentiated support to principals and principal managers by setting clear priorities, aligning initiatives to what matters most for student outcomes, and ensuring leaders are equipped to execute across all elements of high-performing schools
• Shape and drive the strategic direction and organizational health of KIPP Chicago
• Partner with the CEO and Executive Leadership Team to define regional vision, set region-wide priorities, and make critical strategic decisions that advance student outcomes and organizational sustainability
• Collaborate with executive and functional leaders to ensure alignment and coherence across academics, talent, operations, and student services
• Collaborate with the Chief Academic Officer to ensure strong execution of the academic strategy
• Serve as a senior representative of KIPP Chicago internally and externally, engaging with the Board, families, and community partners as a steward of the organization’s mission
• Model KIPP Chicago’s mission, beliefs, and values in leadership practice and decision-making

Benefits

• Competitive executive salary, commensurate with experience and aligned to regional salary bands
• Competitive rates for medical insurance and short-term disability insurance. Dental insurance, vision insurance, life insurance, and long-term disability insurance are offered at no cost.
• Competitive retirement savings benefits: Chicago Teachers Pension Fund eligibility for IL licensed educators or 403B match
• Robust development and professional collaboration within national KIPP Foundation CSO cohort

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed