School Leadership
$50k - $60kGuidepost Montessori
We are always looking to connect with experienced School Leaders across the Downtown Chicago and surrounding Illinois Suburb areas who are interested in future leadership opportunities within our Guidepost Montessori network! We are looking to connect with experienced school leaders who share our passion for Montessori education and who have demonstrated success in building or supporting strong teams, cultivating thriving school communities, and ensuring high-quality educational experiences for children and families. Depending on the specific opportunity, School Leaders within our network may be responsible for leading campus teams, supporting enrollment health, fostering family relationships, and ensuring operational and program excellence. Responsibilities may include, but are not limited to: Supporting a strong, mission-aligned culture on campus that reflects our values Building relationships with families and creating a welcoming, high-quality school experience Leading tours for prospective families and guiding them through the enrollment journey Managing the enrollment process, including lead tracking and follow-up through CRM systems Planning and supporting community outreach events Overseeing key aspects of day-to-day school operations, including billing, supply ordering, and facilities coordination Responding to family questions and resolving concerns with professionalism and care Partnering with school and regional leaders to support overall school performance and consistency What we offer: A network of supportive peers and mentors who regularly share best practices Career growth and promotion opportunities A competitive salary of $50,000 - $60,000 depending on education and experience Health, dental, and vision insurance Paid time off and paid holidays 75% tuition discount for two children at any school within our network (we serve children 3 months through 6 years old) The opportunity to contribute to a high-quality educational program that serves the individual needs of each child We'd love to talk with candidates who: Have experience in early childhood education, school operations, admissions, or leadership roles Are highly organized and able to manage multiple priorities effectively Enjoy working with families and building strong relationships Communicate clearly and professionally, both verbally and in writing Have strong attention to detail and follow-through Are comfortable using systems and learning new tools Take initiative and are willing to step in where support is needed We'd prefer candidates who have: Experience in roles such as school leadership, admissions, program management, or operations Familiarity with the Montessori method of education or Montessori certification Experience using CRM systems and billing platforms Knowledge of the local community to support outreach and enrollment efforts Guidepost Global Education and Guidepost Montessori are committed to a policy of Equal Employment Opportunity (EEO). We will not discriminate on the basis of age, sex, race, color, creed, religion, ethnicity, sexual orientation, gender identity, gender expression, national origin, alienage or citizenship, disability, marital status, military or veteran status, or any other legally recognized protected basis under applicable federal, state or local laws, regulations or ordinances. Our leadership is dedicated to ensuring the fulfillment of this policy. When requested, we are committed to reasonably accommodate employees and applicants with disabilities or special needs that may require an accommodation. #J-18808-Ljbffr Guidepost Montessori
$53.45k - $65.47k
...National Leadership Formation Coordinator The Archdiocese of Chicago, the third largest in the United States, serves more than 2.2 million... ...seminaries. The Archdiocese's 150+ elementary and secondary schools comprise one of the largest U.S. private school systems. Its...SuggestedWork at office- Term Faculty (Non‑Tenure Track) - Leadership, Language, and Curriculum (26-27) Rank: Instructor/Professional Lecturer College/School: Chicago, IL - College of Education Job ID: 182074 We invite applications for a term line position in our Educational Leadership and/or...Suggested
- For over fifteen years, Youth Connection Charter School (YCCS) has served as the leading provider of alternative education programs in the Chicago area. YCCS is the only chartered alternative education system that is solely dedicated to serving the growing population of...Suggested
- ...Job Description Job Description Youth Connection Charter School (YCCS) is inviting a creative, energetic, and enthusiastic High School Math Teacher to work in our small alternative high school setting. Dedicated to serving off-track and out-of-schools students, Youth...Suggested
- ...Job Description Job Description School Leadership Pipeline You Belong Here! If you are interested in joining any of our amazing schools in a leadership role, now or in the future, please submit your resume and credentials. Our schools are located in the city of...Suggested
$50k - $59k
St. Raymond School in Mount Prospect is looking for a dedicated Assistant Principal to support the Principal in daily operations. The... ...involved in scheduling, safety enforcement, and supporting the school leadership. The position offers a competitive salary range of $50,000 - $5...- ...a leading education management organization, Meridian Charter Schools is committed to transforming the lives of students in culturally... ...of the school campus team and will partner with school-level leadership to carry out the responsibilities of this role. You will play...Full timeWork at officeLocal area
- ...Position Type: School Administration/Assistant Principal Date Posted: 4/7/2026 Location: Madison Elementary School (K... ...management, organization, safety, supervision, and educational leadership of the school. The Assistant Principal assumes the administrative...Immediate start
- ...Principal Date Posted: 1/26/2026 Location: Foster School Date Available: 07/01/2026 Closing Date: Until Filled... ...bring stability to a community that has experienced recent leadership changes. Foster is an elementary school serving students K-5. Foster...
$88.23k
School Psychologist (SY26/27) JobID: 5399 Position Type: Related Services/ School Psychologist Date Posted: 4/30/2026 Location: Districtwide... ...with principal as a member of their school's Instructional Leadership Team (ILT) for the purpose of establishing and communicating...InternshipFlexible hours$40k - $50k
...language, coordination, self-regulation, and confidence. Your leadership will empower toddlers to explore freely, make choices, and take... ...~75% tuition discount for up to two children at any Guidepost school ~ A collaborative, supportive network of peers and mentors...Local area$150k
...student reaches 99%, your task is to uncover what prevented 100%) Leadership And Growth Coach Key Responsibilities Drive exceptional student... ...in non‑academic settings (community organizations, after‑school programs, sports camps) Comfort presenting to and building trust...Full timeFor contractorsWork at officeImmediate startRelocation packageDay shift$39.92 - $69.92 per hour
...Description Job Description Bachelor's or Master's degree in School Psychology, active School Psychologist license and minimum 1+... ...schools. Exposure to diverse educational practices and district leadership styles will enhance your skills, strengthen your resume, and...Full timeLocal areaWeekend work$44.92 - $64.92 per hour
...Description Job Description Bachelor's or Master's degree in School Psychology, active School Psychologist license and minimum 1+... ...June 11, 2027) exposes you to diverse workplace practices and leadership styles across elementary, middle, and high school settings. Your...Full timeLocal area$44.92 - $64.92 per hour
...Description Job Description Bachelor's or Master's degree in School Psychology, active School Psychologist license and minimum 1+... ...middle, and high school settings, engaging in cross-disciplinary leadership and professional growth. Expanding your resume has never been...Full timeLocal area$40 - $60 per hour
...Description Job Description Bachelor's or Master's degree in School Psychology, active School Psychologist license and minimum 1+... ...school, and strengthen your resume with new evaluation methods and leadership in problem-solving. During your downtime, explore local parks,...Full timeContract workLive inLocal areaMonday to Friday$44.92 - $64.92 per hour
...Description Job Description Bachelor's or Master's degree in School Psychology, active School Psychologist license and minimum 1+... ...set your resume apart and foster the development of versatile leadership skills. What We’re Looking For: Current School Psychologist...Full timeFlexible hours$40 - $60 per hour
...Description Job Description Bachelor's or Master's degree in School Psychology, active School Psychologist license and minimum 1+... ...assignment for broadening your resume and opening doors to new leadership experiences. Plus, the built-in flexibility of a travel contract...Full timeContract workLocal area- ...Job Description Job Description Job Description: High School Special Education Teacher Reports To: Principal Apply today... ...and curriculum identified by the school Instructional Leadership Team. Produce and share lesson plans in accordance with the procedures...Full timeLocal areaFlexible hours
- Charter One works with schools across the country to provide all-inclusive education management services. At Charter One we pride ourselves... ...of the school are being carried out properly. American Leadership Academy is now accepting applications for High School...
- The National Association of Independent Schools is seeking a Dean and Director for the University of Chicago Laboratory Schools in Chicago... ...community. The ideal candidate will have strong educational leadership skills, a commitment to diversity, and the ability to engage...
$28 - $32 per hour
...Position Type: Maintenance/Custodial/Head Custodian Date Posted: 5/6/2026 Location: Marie Murphy School Date Available: 07/01/2026 Marie Murphy Middle School Head Custodian /Bus Driver 05/05/2026 CLASSIFICATION: Non-exempt; Buildings &...Hourly payFull timeWork at officeNight shiftAfternoon shift$60 - $68 per hour
26/27 School Year | $60-$68/hour | Full-Time | Chicago, IL | PEL with School Psychologist Endorsement Required About the Role... ...: students first. Guided by a growth mindset, courageous leadership, and a deep culture of collaboration, fun, and determination, our...Full timeTemporary workWork at officeLocal area- ...The IB Teaching Style All Staff Responsibilities: Ensure a safe school environment, both indoors and outdoors, in accordance with... ...instructional practices, with a focus on student growth. Collaboration & Leadership Guide and coach the PYP Support Teacher to facilitate small...Hourly payFull timeImmediate startMonday to FridayMonday to Thursday
- Celebree School of Northbrook is hiring a Lead Teacher for the infant room to create and implement lesson plans, manage classroom activities, and support assistant teachers. Ideal candidates should have a strong understanding of early childhood development and experience...
$60k
...transparently with clear performance metrics, student outcomes, and leadership contributions. At Kairos, teachers are deeply valued... ...lasting relationships that enhance student persistence and the school community. Proficiency with Microsoft Office, instructional technology...Work at officeMonday to FridayWeekend workAfternoon shift$20 - $27 per hour
A community-focused educational nonprofit in Chicago is seeking an instructor to teach a leadership development program for high school teens. The role requires leading hands-on activities that nurture leadership skills and civic engagement. Ideal candidates should have...Hourly pay$90k
Title: Assistant Principal Location: CICS Longwood High School- 1309 W 95th St, Chicago, IL 60643 Reports To: Principal Salary: Starting... ...routines, procedures, and expectations Instructional Leadership 60% ~Serve as the model for instructional and social-emotional...Full timeSummer workSummer holiday$40k - $50k
...paid holidays ~75% tuition discount for up to two children at any Guidepost school ~ A supportive network of passionate educators ~ Clear opportunities for career growth and leadership advancement About Guidepost Montessori Guidepost Montessori is a...Local area- ...Job Description: School Social Worker Reports To: Principal Apply today: Overview As a leading education management organization... ...will report to the Principal or designated member of the leadership team, will serve as a member of MTSS/RTI team, and will partner...Full timeLocal areaFlexible hours
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