Assistant Superintendent, Middle School

Posted on: August 11, 2021 | |

ReGeneration Schools is a school management organization that oversees four K-8 elementary schools in Chicago, IL, and Cincinnati, OH, that serves over 1,700 low-income students. Our mission is to ensure that all children have access to a high-quality, college-preparatory education through academic excellence and the content of their character. We are accomplishing this mission every day, moving from the bottom 17% of the state to the top 39% for student achievement.

We are looking for a dynamic Assistant Superintendent (Middle School) to help drive the success of our schools and principals. Reporting to the Superintendent, the Assistant Superintendent oversees instructional and academic programs for all middle schools within the network and is accountable for developing principals and student success and achievement within their schools. This individual serves as a vital member of the Instructional Executive Leadership Team to ensure alignment with instruction and school culture that supports ReGeneration’s mission and vision of a joyful learning environment.

Who Should Apply?

As a member of the Instructional Executive Leadership Team, the Assistant Superintendent (Middle School) must have strong content and pedagogy knowledge and strategically use data to identify gaps and opportunities in instruction. They are effective in developing school principals’ practice to become impactful leaders (as well as model expectations), communicates with enthusiasm to curate meaningful relationships with all stakeholders, a critical thinker and solution-oriented, with an unyielding belief that all students deserve the best education to give them access to transformational opportunities. They are also self-reflective, open to feedback, and committed to continuously improving. At least 3-5 years of School Principal experience is required with impactful growth in student achievement data.

Academic Program:

Using data and daily observations, partner with Principals to consistently evaluate and improve instruction, teacher training and coaching, curriculum implementation, assessments, and other aspects of schools’ academic programs and culture;
Partner with Principals to a build positive culture with staff, students, and families:
Support Principals to plan and implement summer and school-year training and professional development for teachers;
Work with Principals and Case Managers to ensure that teachers are implementing special education services by the state law;
Support Principals to oversee the hiring of teachers and other school staff.

Development of Principals and Instructional Leaders:

Provide frequent, informal feedback (includes modeling) to Principals and conduct annual formal evaluation;
Plan and implement training for Principal Fellows and all network instructions leaders;
Recruit for and participate in Principal and instructional interview process;
Support, develop, and execute Principal professional development;
Build a personal and professional network to cultivate future instructional and leadership talent at ReGeneration.

Network-wide Instruction:

Build a cohesive, consistent culture of schools through Principal meetings and communications;
Ensure assessments, reports, and other data needs are managed and implemented by instructional leaders and school-based operations staff.

ReGeneration’s Mission and Vision:

Provide and model leadership to all staff, students, and families in establishing a joyful, structured, and achievement-oriented school culture;
Partner with ReGeneration School Leaders to support operational and compliance needs;
Partner with the Home Office to meet organizational needs, including development, marketing, and recruitment;
Serve as a member of the ReGeneration Schools Instructional Executive Leadership Team.

Leadership Support

At ReGeneration, it’s a collective effort to ensure everyone is successful in their role. Here’s how we support our Assistant Superintendent (Middle School):

Weekly planning meetings with the Superintendent to support and advise on school performance data meetings, network professional development, school shadowing and walkthroughs, milestones and goals, etc.
1:1 coaching and professional development with network external consultants.


In addition to developing school principals and that academic program, the Assistant Superintendent (Middle School) has an excellent opportunity to create school culture initiatives that will spark joy and engagement for students and staff at each campus.


Strong belief that disadvantaged youth can become college and career-ready.
Track record of leading students and staff to outstanding results.
Adapt problem solver with a demonstrated ability to think critically, plan strategically, as well as research and perform detailed data analysis.
Exceptional written and oral communication to diverse audiences and facilitating decision-making among multiple parties.
Proactive and fast learner who thrives in a fast-past environment and implements with urgency.
Ability to provide high leverage feedback via classroom observations and school walk-throughs.
Takes personal responsibility and is committed to continual professional growth.
Strong organizational and time management skills, detail oriented, and consistent follow through.
High expectations for personal and team performance.?
Flexible to changing priorities and conditions.
Belief and alignment with ReGeneration’s core beliefs and educational philosophy.
Experience using data to lead others towards the improvement of student outcomes.
Reflective about personal strengths and weaknesses and able to effectively balance confidence with humility.?
Illinois State license is a bonus but not required.
3-5 years of School Principal experience in a high-performing urban school required.?
Strong math content is preferred.
Bachelor’s degree is required; graduate degree in education, public policy, or related field is strongly preferred.

Start Date: ASAP participate in summer professional development for school principals and all school staff. The school year is July – June, with winter, spring, and summer breaks.



ReGeneration Schools offers a competitive salary based on experience with a generous benefits package. In addition to extensive professional development, all staff is equipped with a laptop, email, and necessary supplies. School leader relocation stipend provided for out-of-state hires.

ReGeneration is committed to building a talented team that reflects diversity in experiences and culture to enable our scholars to thrive. We also work to ensure an inclusive community by creating a space for meaningful dialogue about race and identity issues for our staff and students. ReGeneration is an equal opportunity employer and will not discriminate against any employee or applicant based on race, color, creed, religion, gender, sexual orientation, national origin, marital status, age, or disability.