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Regional Superintendent

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Stronger Consulting
Full Time position
Listed on 2026-09-18
Job specializations:
  • Management
    General Management, Healthcare Management, Area Manager
Salary/Wage Range or Industry Benchmark: 310000 - 345000 USD Yearly USD 310000.00 345000.00 YEAR
Job Description & How to Apply Below

About The Position

The Regional Superintendent is one of the most important leadership roles at the KIPP Foundation. This person is directly accountable for performance of a portfolio of KIPP regions, and their primary lens is always instructional. Student learning outcomes are the center of gravity for this role, and everything the Regional Superintendent does is ultimately in service of ensuring that every school in their portfolio is delivering a meaningful, high-quality education for kids.

The Regional Superintendent is responsible for the performance of every region in their portfolio and drives results through the Executive Directors they support and supervise. They know what excellent school districts look like, they can articulate what it takes to get there, and they hold EDs accountable for building toward that standard with rigor and consistency. Coaching and development are central to how the work gets done — the core coaching relationship in this role is about developing EDs who can make their schools instructionally excellent — not just organizationally functional.

In most regions, this looks like ensuring EDs have the content knowledge, skills, and systems to effectively manage and develop their Chief Academic and Chief Schools Officers, those senior leaders responsible for running the academic systems required to ensure excellence in teaching and learning. While the Executive Director is responsible for running the region — its finances, governance, talent systems, and operational infrastructure — the Regional Superintendent is responsible for ensuring the region has an ED capable of doing so.

The health of the region is ultimately the Executive Director's responsibility to own and run. The Regional Superintendent's role is not to manage those functions directly, but to help EDs avoid serious mistakes, recognize when a situation is escalating beyond what an ED can manage, and surface those situations to the Chief of Regional Impact before they become crises. When an ED cannot meet the bar even with coaching and support, the Regional Superintendent is responsible for surfacing that judgment and acting on it.

This is also a systems and process role. The Regional Superintendent sees across their portfolio, identifies where regional performance is falling short, and builds clear action plans rooted in the habits and systems that drive school improvement—data-driven instruction, intellectual preparation of teachers and leaders, and strong organizational accountability. They are skilled at a particularly important diagnostic question: why isn't all of this expertise making systemic impact?

And they help their teams find and act on the answer. The Regional Superintendent is a senior leader who operates with strong judgment and high standards. This role works within the instructional vision set by the Chief Schools Officer and within the framework of our One KIPP strategy. The right candidate is a critical thinker and a results leader who understands that coherence across the network is a feature, not a constraint.

They work in close partnership with three peer Regional Superintendents, the Chief of Regional Impact, and the Chief Schools Officer to ensure their work is unified and mutually reinforcing across the full network. They manage a team of Regional Impact teammates responsible for providing coaching and direction to the Chief Academic and Chief Schools Officers on the installation and improvement of our highest priority academic systems.

The Regional Superintendent reports to the Chief of Regional Impact.

Executive Director Accountability and Instructional Leadership
  • Hold EDs accountable for performance against anchor metrics by providing direct and candid feedback and…
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