High School Assistant Principal

Title: Assistant Principal
Location: CICS Longwood High School- 1309 W 95th St, Chicago, IL 60643
Reports To: Principal
Salary: Starting at $90,000, commensurate with experience
Employee Type: Regular Full Time
Start Date: August 2026

Distinctive Schools creates diverse, joyful, welcoming communities rooted in social justice and rigorous learning. We support all learners to be engaged, curious, and to achieve their full potential. Our students become confident advocates, creative problem-solvers, and collaborative leaders.

Position Overview

The Assistant Principal is a self-driven and motivated educational leader whose philosophy and beliefs align with Distinctive Schools' mission, vision and values. The Assistant Principal has a keen instructional lens and is able to provide targeted and actionable feedback.

Primary outcomes of the role is to:

• Implement the DS instructional coaching model by supporting and fostering the development of teachers and instructional coaches
• Facilitate and monitor the formal and informal observation processe
• Oversee all MTSS efforts and processes to support student learning including data, planning, and problem-solving meetings
• Support school-wide academic and social and emotional learning to reinforce safe, joyful, and personalized learning environments

Responsibilities

School Culture 10%

• Build and foster a culture of belonging, joy, and a positive climate
• Honor stakeholder perspective as key to the decision-making process
• Cultivate a strengths-based and, equity-focused mindset
• Celebrate individual and collective growth towards goals
• Promote a safe, supportive, and collaborative working environment with an equity-conscious mindset.
• Establish professional rapport with and maintain visibility with stakeholders
• Lead the equity work of the campuses and engage in culturally responsive, student-centered decision making
• Develop positive and professional relationships
• Create and implement consistent routines, procedures, and expectations

Instructional Leadership 60%

• Serve as the model for instructional and social-emotional best practices
• Serve as a member of the school's Instructional Leadership Team (ILT) to support alignment, including and performing other ILT duties (in Professional Learning and Leadership)
• Execute and monitor the campus growth plan in alignment with DS strategic plan in partnership with the School Principal
• Develop, implement, and oversee specific projects based on the unique needs of the campus and in alignment with the campus growth plan efforts, and student-centered learning initiatives in partnership with ILT
• Oversee campus implementation of DS MTSS processes, protocols, and tools with ongoing collaboration with network teams
• Uphold and support successful implementation of core curriculum and assessments
• Meet regularly with Teacher Leaders and Teachers weekly in accordance with DS model with the Instructional Coaches individually at least bi-weekly to prioritize coaching caseload and determine action steps
• Provide actionable feedback to teachers and teacher leaders to support their professional growth and development and ensure follow-through
• Meet with the Mentor Teachers individually or as a team at least monthly to problem-solve and determine action steps
• Provide goal-oriented feedback to Teachers, including Instructional Coaches and Mentors, to support their professional growth and development
• Conduct formal observations in adherence to regional expectations and protocols
• Coordinate and oversee all required testing administration in partnership with the Principal and Director of Data and Assessment
• Plan and present ongoing professional development and collaborative planning sessions
• Oversee the implementation and data analysis of instructional technology and online programs
• Monitor and ensure staff adherence to the norms outlined in the DS Professional Expectations and Responsibilities
• Conduct daily teacher observations and classroom visits and provide real-time, high-leverage feedback to improve student achievement and instructional effectiveness

Instructional Coaching 10%

• Exemplify and support the DS instructional coaching model, including facilitation of deep coaching cycles based on teacher need and experience
• Move the performance of individual Teachers through goal-setting, observation, co-teaching, modeling, and goal-specific feedback
• Model specific teaching skills or strategies for teachers through the use of video and classroom instruction
• Create coaching tools (e.g., checklists, observation protocols, conversation agendas, etc.) to support each teacher's progress towards and achievement of the goal
• Support the Lead Instructional Coach in prioritizing the needs of teachers who need intensive and ongoing support (i.e., first-year teachers)
• Provide weekly (minimum) coaching for those teachers actively participating in a deep coaching cycle, including those on a Direct Support Plan (DSP)
• Document and model documentation of deep coaching work
• Monitor instructional coaching documentation

Assessment and Data Analysis 10%

• Review & analyze campus academic and behavior Tier 1, 2, and 3 data (e.g, universal screeners and core program assessments, digital program data, check-in/out, etc.). Update the ILT and DS Academic Team on progress
• Assist with coordination of the campus' academic and behavior universal screening process
• Maintain accurate records of student progress toward standards, intervention progress monitoring, and digital program data in established network systems
• Collaborate with Instructional Coaches and Mentor Teachers to model and support strong data analysis, and lesson design during weekly planning meetings
• Facilitate grade or team Data & Design meetings as assigned by the Principal
• Seek out, be receptive to, and respond to professional feedback

MTSS Processes 5%

• Review lesson plans and provide feedback based on individual coaching cycles and/or school-wide professional development goals
• Lead MTSS initiatives, processes, and structures at the campus level and contribute to network MTSS design
• Facilitate campus and grade level problem solving meetings ensuring evidence-based decision making for Tiers 1, 2, and 3 responses and interventions
• Collaborate with school team to design, develop, document and implement a continuum of effective, research-based and innovative interventions and instructional supports as part of a multi-tiered system of supports
• Model and coach teachers in effective Tier 1, 2, and 3 instruction and implementation
• Support communication with families on MTSS processes, intervention and student progress
• Pilot tools, resources, data collection and programs in partnership with the network academic team

Professional Learning and Leadership 5%

• Participate in all network and campus-based professional development and meetings
• Meet with the Regional Talent Development Manager, Director of Instructional Coaching at least biweekly to discuss coaching priorities, implementation of the coaching model, and instructional coach development and support
• Serve as a member of the school's ILT to support alignment and to perform additional ILT duties
• Plan and facilitate weekly campus professional development and collaborative planning, including Welcome Week
• Collaborate with Instructional Coaches and Mentor Teachers to ensure strong data analysis and planning
• Fulfill all other duties as assigned

Requirements (minimum)

Education:Bachelor's Degree

Qualifications

• Valid Professional Educator License or equivalent in state of employment (IL or MI)
• Valid Principal or equivalent endorsement in state of employment (IL or MI) - OR - working towards a General Administrative/School Principal Endorsement
• 6+ years of lead classroom teaching experience
• 2 years of instructional leadership experience
• Must obtain an average of 'Effective' rating according to the DS Teaching Frame]work for 2 consecutive years at DS in all domains or equivalent from outside organization
• Must attend DS Summer PD Institute
• Proven success of leading team planning sessions using data
• Must be willing to work an extended academic calendar year of 12 months
• Technology demands:
  • Proficient with cloud based software solutions (such as GoogleSuite)
  • Ability to learn digital tools and programs as needed for the position
  • Travel as required for training, professional development, and collaboration

Physical demands

• Ability to work outside of normal school hours as needed and/or determined by School Principal
• Occasional lifting, carrying, pushing, and/or pulling; some stooping, kneeling, crouching, and/or crawling; and significant fine finger dexterity. Generally, the job requires 20% sitting, 50% walking, and 30% standing

Benefits

• 25+ Paid holidays & 10 days PTO annually (in addition to summer break for educators/campus positions)
• 12 weeks family paid leave
• Comprehensive Healthcare (Medical, Dental, Vision)
• 403b match
• Fully match up to 3%
• 50% match up to 5%
• Professional development including tuition reimbursement
• Gym and wellness discounts
• And more

Description Disclaimer : Since no job description can detail all the duties and responsibilities that may be required from time to time in the performance of a job, duties and responsibilities that may be inherent in a job, reasonably required for its performance, or required due to the changing nature of the job shall also be considered part of the jobholder's responsibility.

EEO

Distinctive Schools is an equal opportunity employer and does not discriminate against any employee or applicant for employment on the basis of race, color, religion, sex, gender, national origin, age, disability, veteran status, marital status, sexual orientation, gender identity, gender expression, or any other personal characteristic protected by applicable law.
Distinctive Schools is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Distinctive Schools will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact View email address on click.appcast.io or call View phone number on click.appcast.io