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Full-time ,
submitted by
Maggie Baker

Progressive Educator

  • Are you convinced that the way we are educating children has to fundamentally change?
  • Do you have the patience needed to allow students to experience and learn from failure?
  • Are you prepared to inspire a generation to tackle the challenges that lie ahead?

Greenfields Academy is a progressive, independent private school serving children in K through 12th. We believe in student-driven learning, where each child is encouraged to set their own goals and pursue their passions through independent work and project-based learning. Our approach to learning does not include tests, grades, or teachers leading lectures. Our classroom structure ensures that the adult creates and facilitates the learning environment, but empowers students to take ownership of their individual learning path and collective classroom governance. Our students are on a Hero’s Journey to change the world!

We are currently interviewing for a full-time Apprentice Guide (our word for teacher) for our 6th -12th grade students. In particular, we are seeking candidates with experience creating and leading curriculum for Project-based learning. As our school has plans to expand, this position has excellent opportunity for growth and advancement to become a lead guide of their own studio. Responsibilities may include:

  • planning overarching curriculum for project-based learning about a series of unique topics
  • mentoring and coaching students both one-on-one and in small groups
  • maintaining a studio environment that supports and motivates children
  • supporting individuals in setting and achieving their personal learning goals
  • assisting children in identifying and pursuing their passions
  • planning our weekly Discovery Days, including workshops, visiting speakers, and field trips.
  • facilitating Socratic group discussions
  • documenting learning through observation and assessments
  • communicating with parents to build strong relationships
  • participating as a supportive, dependable, and energetic member of our team


We are looking for a candidate with proven excellence working with children in a non-traditional learning environment: free school, homeschool, Montessori, Reggio Emilia, project-based, camps, afterschool or other student-directed settings. In particular, we are seeking candidates with multiple years of working with students in grades 6-12 and with experience designing and implementing project-based learning curriculum. Candidates should demonstrate a lifelong love of learning, ability to build authentic relationships with children, a strong work ethic, and willingness to let the students co-create and lead their learning. Candidates should be comfortable using and learning a variety of technology tools. And most importantly, candidates should have a deep respect for all children.


Pay is commensurate with education and experience. We will assist with relocation expenses for the right candidate.

Next Steps:

To apply, please send your resume and a thoughtful cover letter to

Contact Info:
Maggie Baker
Job Type: Permanent
Location: Chicago, IL