Employment Opportunities

Director of Finance and Operations

Urban Prairie Waldorf School seeks an innovative thinker who is disciplined in both thought and action, is collaborative and decisive, and will support our pedagogical goals and priorities. The school is in the third year of a new governance structure and an administrative restructuring and expansion. The Director of Finance and Operations joins our administrative senior leadership team, including Head of School, Director of Curriculum and Instruction, and Director of Enrollment Management.

We are a diverse community of families, 40% non-white. The diversity of our faculty and staff is growing, and we would like very much for our leadership and administration to reflect the diversity of our city and of our current and future students.

UPWS compensation includes a competitive salary, medical, short-term disability, long-term disability, and 401K benefits.



  • Maintain current, accurate financial records of operations and the financial position of the school. 
  • Create, provide, and maintain monthly reports for financial management and reporting to the Board of Trustees. 
  • Oversee and lead annual budgeting and planning process in conjunction with the senior leadership team and Board. 
  • Manage cash flow effectively and revise, monitor, and maintain internal control structure
  • Prepare, implement, and manage annual operating budget and Annual Plans
  • Oversee financial protocols and contracts for alternate streams of revenue
  • Serve on the Finance Committee for the Board of Trustees
  • Provide expertise in data analysis and decision making
  • Process biweekly payroll
  • Coordinate, evaluate, and manage school bookkeeper’s regular work
  • Track and monitor all sources of income
  • Manage billing and payment processing
  • Take necessary action on delinquent accounts through collaboration with Head of School


  • Hire, manage, monitor, and assess operations staff
  • Manage relationships and contracts with external vendors
  • Create and implement campus safety and risk management protocols
  • Develop annual budget for facility maintenance and improvements

Candidate Qualities and Capacities

  • Ability to set priorities, organize, analyze, work independently, meet deadlines, problem solve, initiate business practice innovations and multi-task.
  • Strong interpersonal skills to work effectively with multiple constituencies, such as faculty administrators, volunteers, parents, students, board members and contract workers.
  • Ability to think strategically at the 10,000-foot level allowing the organization to grow and shift to meet industry demands.
  • Commitment to understanding diversity in our school community and our surrounding neighborhood community and bringing this as part of our students’ education.  
  • Ability to work in a collaborative manner in an environment of mutual support.
  • Flexibility and a growth mindset.
  • Commitment to personal and professional growth.
  • Strong verbal and written communication skills. 

Qualifications and Requirements: 

  • Bachelor’s degree.
  • Experience in a similar role involving strategic and day to day financial and operational management. Work experience in an educational institution is preferred.
  • Proficiency with organizational budgeting and financial management. Experience with and understanding of general accounting (GAAP), payroll management, human resources, and general business systems and functions. Demonstrated success in developing and monitoring financial systems.
  • Knowledge of and experience with human resources and facilities management.
  • Non-profit or small business operations experience is a plus.
  • Familiarity with local, state, and federal educational regulations preferred.
  • Working knowledge of Microsoft Word and Excel, Google Suite, and QuickBooks.
  • Familiarity with Human Resources and payroll platforms preferred.

Starting salary is competitive and takes into consideration years of experience. Applicants should send a letter of interest, resume, and three references to jobs@urbanprairie.org. Urban Prairie is an equal opportunity employer. 


Early Childhood Lead Teacher

Urban Prairie Waldorf School on Chicago’s near west side seeks an Early Childhood Lead Teacher to join our faculty for the 2022-23 school year. Candidates should send a letter of interest, resume, and three references to jobs@urbanprairie.org.

Qualifications and requirements:

  • Enthusiasm for facilitating a Waldorf education that is relevant to the 21st-century urban child and nurtures societal and ecological responsibility
  • Commitment to being culturally competent and understanding diversity in our school community and our surrounding neighborhood community, bringing a culturally responsive and sustaining education
  • Commitment to working with colleagues and directors to take recognizable action toward making the UPWS curriculum increasingly more inclusive of diverse persons and viewpoints, especially those that have been and are underrepresented
  • Ability to work in a collaborative manner in an environment of mutual support
  • Ability to self start, take the lead, and work independently within the context of the school’s shared agreements
  • Flexibility and a growth mindset
  • Commitment to personal and professional growth
  • Strong verbal and written personal communication skills with the ability to communicate with and listen effectively to colleagues, parents, and guardians
  • Fluency in Spanish preferred, with an interest in bringing the language to the classroom
  • Waldorf teaching experience preferred
  • Bachelor’s Degree preferred
  • A minimum of 3-5 years of experience in education preferred
  • Waldorf teacher training certification completed, underway, or a commitment to beginning within the first year of employment at Urban Prairie

Substitute Teachers (General)

Urban Prairie Waldorf School invites experienced teachers, advanced M.Ed. students, and Waldorf teacher training students to apply for this wonderful opportunity to gain hands-on experience teaching Waldorf education, in the classroom, and if needed during COVID, as part of hybrid or distance learning. Lesson and classroom guidelines will be provided for each grade.

To join the list, please send a note of introduction and a summary of your qualifications here ».

Our Policy


Urban Prairie Waldorf School is committed to providing a work environment that is free of any type of discrimination or harassment. It is Urban Prairie’s policy to provide equal employment opportunity to all employees and applicants for employment with regard to race, color, sex, religion, gender, gender identity, national origin, age, sexual orientation, disability, pregnancy, childbirth, or related medical conditions, or any other protected characteristic, in accordance with applicable federal and state laws. This policy applies to all terms and conditions of employment, including, but not limited to, hiring, placement, promotion, termination, compensation, and training. In keeping with this commitment, sexual harassment and harassment on the basis of an individual’s race, color, religion, gender, gender identity, national origin, age, sexual orientation, disability, pregnancy, childbirth or related medical conditions, or any other protected characteristic, will not be tolerated by Urban Prairie. This includes harassment by or against teachers, administrators, staff, students, trustees, parents, and visitors. It is also a violation of this policy to commit or engage in any unprofessional or inappropriate conduct based on any protected basis, whether or not such conduct rises to the level of unlawful. Anyone who engages in any action or conduct that violates this policy will be subject to appropriate disciplinary action, up to and including termination.