Chicago Free School is hiring for two positions – a Middle School Teacher to join our dynamic, visionary teaching team, and an Operations and Finance Coordinator to manage our finances and keep the administration of our school running smoothly. Please click on the links below for job descriptions and information about how to apply.

Middle School Teacher

Operations and Finance Coordinator


Middle School Teacher, January 2020

We are hiring a middle school teacher to begin January 2020. Are you a teacher with a vision of what student-centered learning can be? Interested in joining a creative, thoughtful, collaborative team? Read below for the job description and information about how to apply.

Chicago Free School is seeking a creative, motivated middle-school teacher who is passionate about student-led learning. We seek to foster a sense of ownership and self-motivation in students and are looking for a middle-school teacher who enjoys connecting students with engaging, authentic learning experiences that help them grow as a whole person.

Chicago Free School Middle School Teacher Job Description

Homeroom Teaching, mornings and all day Fridays.

  • Advise a homeroom group of 10-15 students in 6th, 7th, and 8th
  • Develop, adapt, and teach math and literacy curricula that incorporate student interests, teacher interests, and core subject competencies. Subject matter should be geared toward middle school students and centered on project-based, interdisciplinary, service-learning, hands-on, and inquiry-based modes of learning. Teachers have significant autonomy to develop fun, purposeful, and creative learning experiences in partnership with students. We employ flexible grouping based on students’ individual development.
  • Incorporate social justice as a core curricular focus according to an intersectional, anti-oppression lens.
  • Organize and lead frequent field trips connected to learning themes. Involve students in the field trip planning process.
  • Support students’ individual development, goal-setting, and self-directed learning. Support students’ intrinsic motivation. Support students’ completion of independent projects and activities in literacy, math, and other subject areas.
  • Use formal and informal assessment strategies to track student progress and development.
  • Use community-building activities and structures to promote a positive, productive, and inclusive classroom environment.
  • Teach social and emotional skills through advisory activities and individual coaching.

Afternoon Teaching, Mondays-Thursdays

  • Teach elective subject-area classes (such as painting, chemistry, or architecture) to students at a variety of grade levels.
  • Lead clubs based on student interests.
  • Supervise students during outdoor play.

CFS Philosophy of Conflict Resolution

  • Support students in democratic resolution of conflicts using a process similar to restorative justice.
  • Communicate respectfully and non-coercively with students to enforce school rules in order to foster a safe and positive classroom culture.
  • Balance supporting students in developing independence and autonomy while maintaining a safe learning environment.

Family Communication

  • Develop personal, supportive relationships with families of homeroom students.
  • Write narrative reports 2 times per year and participate in student-led conferences to share with families about what students have been learning and doing.

Administrative Roles

  • Participate in a collectively-managed staff to make administrative and operational decisions in partnership with the board of directors. Decisions are made by consensus. We do not have a principal or director.
  • Take on an administrative role such as fundraising, parent communication, or facilities management in coordination with building landlords. Staff share administrative responsibilities with a full-time administrator.

Expected time with students per week – 30 hours, expected planning time per week – 8-10 hours/week, expected administrative time per week – 5 hours/week, expected meeting time per week – 2 hrs/week.

School session for teachers – Mid-August to mid-June.

Starting salary – $50,000 per year plus medical and dental benefits.

Required Qualifications

  • Bachelor’s degree.
  • Experience working with middle-school/junior high students in an educational setting.
  • Experience taking initiative and bringing projects to completion.
  • Track record of creating a positive classroom/school culture among young adolescents.
  • Track record of teaching according to a student-centered, student-directed model.
  • Track record of teaching multiple subjects or taking an interdisciplinary approach to teaching.

In Place of a Cover Letter, Please Answer the Following Questions in 2 Pages or Less:

  1. Why are you interested in working at the Chicago Free School?
  2. What strengths will you bring to our work to build the Chicago Free School?
  3. Describe your approach to working with 11- to 14-year old students to support the particular needs of this age group with regard to social, emotional, and intellectual development.
  4. Talk about a math lesson or math-themed hands-on activity that you have led as an educator that you feel was particularly successful or engaging to students.
  5. Talk about a project-based, hands-on, interdisciplinary, or inquiry-based lesson or activity you have led as an educator that you feel encapsulates some part of your vision for what education should be.

In addition to your writing, please include lesson plans, photos, and/or samples of student work to accompany your answers to questions 4 and 5. Please submit your answers and portfolio documents as an MS Word or PDF document.

Send your resume and application materials via email to

Operations and Finance Coordinator

At Chicago Free School (CFS), we believe in empowering students to take ownership of their learning. In our school, learning is hands-on, joyful, and connected to the wider world. The student is at the center of everything we do and our curriculum is driven by student choice, initiative, and inquiry.

The School is now accepting applications for Operations and Finance Coordinator to begin immediately. The Operations and Finance Coordinator works in concert with the teachers and the board to carry out the operational and administrative duties that keep the school running, including bookkeeping, billing, and communication with families.

The ideal candidate is an efficient and effective self-starter and a leader who is able to work with significant autonomy. The candidate will demonstrate the ability to develop, implement and maintain the operational and financial procedures of the school. The ideal candidate will work in close cooperation, under a consensus-based decision making model, with teachers, other staff, and members of the Board of Directors. The candidate will demonstrate competence to ensure that legal and policy requirements are maintained with regard to people, property and function of the School, and will manage school resources strategically. The ideal candidate will carry out the administrative duties of the school with integrity, sensitivity, and professionalism to build trusting relationships with staff and families.



  • Commitment to CFS mission and vision.
  • BA/BE/BS or higher required. A degree in a business management field preferred. A degree in a non-business management related field will be considered with significant direct professional experience in corporate bookkeeping and/or payroll, office administration (particularly school administration), non-profit administration, or a combination of these experiences.
  • Demonstrated ability to work patiently, independently and resourcefully to problem-solve and achieve objectives in accordance with school policy.
  • Availability for 1-2 evening meetings/events per month and occasional weekend events.
  • Skilled in using office technology to drive analysis, decision making, communication (both internal and external), and collaborative decision-making across multiple audiences of diverse backgrounds.
  • Experience working in Quickbooks, or comparable recordkeeping packages.


  • Experience in the creation of large and complex organizational budgets, and the analysis and measurement of actual performance versus budget.
  • Experience with payroll and payroll related issues.
  • Experience working with external auditors.
  • Knowledge of and commitment to democratic governance processes.

Description of Key Duties:

  • Establish effective working relationships with all stakeholders.
  • Actively promote the values and ethos of the School; act as a positive role model to all members of the school community. Serve as the primary point of contact for the community and families with regard to administrative matters.
  • Work directly with the staff and Board of Directors to ensure the School operates within an effective system of administration and financial management and control.
  • Maintain and document administrative and financial processes, and maintain and manage administrative and financial systems in accordance with the School’s mission and objectives.
  • Perform daily bookkeeping including payroll processing, expense management, bill payment, invoicing, collection of monies, receipt management, preparing accounts for reconciliation, and banking (both virtual and physical).
  • Work directly with the staff and Board of Directors to ensure the School meets all statutory and legal requirements concerning administration and financial management, including compliance with insurance and tax regulations. Generate and file ISBE/Federal administrative paperwork.
  • Together with the Treasurer of the Board of Directors, support the annual external audit process.
  • Together with the Treasurer of the Board of Directors, support the annual budget development and approval process.
  • Identify, and inform the Treasurer of the Board of Directors of, any budget variances and corrective actions required.
  • Propose revisions to the budget if necessary in response to significant or unforeseen developments.
  • Generate and deliver administrative and financial reports as needed.
  • Support internal and Board of Director level committees as needed.
  • Administer and manage the School’s external vendor system for enrollment and billing and the School’s external vendor system for accounts receivable management
  • Develop, implement and revise as necessary existing financial systems to efficiently support the functions of the School.
  • Undertake professional development and training necessary and appropriate to the job.
  • Undertake other duties which are commensurate with the grade and level of responsibility of the post.

Physical Requirements:

  • The physical requirements of this job include light office work, with occasional medium work required for meetings or events.
  • Close visual acuity to perform activities such as preparing and analyzing data and figures, transcribing, viewing a computer terminal, extensive reading, and preparing presentation materials is required.


  • This is a full-time, salaried, professional position.
  • Attendance is required at weekly staff meetings.
  • Attendance is required at monthly evening Board meetings.
  • Occasional additional after-hours, evening, and weekend hours will be required for meetings and events.
  • Some scheduling flexibility to afforded to offset evening time requirements.


  • Salary: $50,000.
  • Medical and dental benefits.
  • Five weeks paid time off per year including sick, personal, and vacation time.
  • Staff members whose children attend CFS receive a 50% tuition discount.

How to apply:

  • Please send your resume and answers to the application questions below to
  • In place of a cover letter, please answer the following questions in two pages or less.
    1. What interests you about this position and about our school?
    2. What strengths do you bring to this position?
    3. Describe your experience with bookkeeping and accounting, including your familiarity with the quickbooks bookkeeping software.
    4. Tell about a time in a professional context when you have taken initiative to improve a system, process, procedure, or outcome for your organization. Describe the steps you took and the results of your efforts.
    5. Tell about a time in a professional context when you successfully worked with a diverse coalition of colleagues, clients, or stakeholders to make decisions democratically. Describe your role in the decision-making process.

Non-discrimination Statement:

  • The Chicago Free School does not discriminate on the basis of race, color, national or ethnic origin, religion, disability, sexual orientation, gender identification, or family income in the administration of its educational policies, tuition assessments, admissions and other school-administered programs.
  • People of color are especially encouraged to apply.