Founding Teacher for new Microschool in Chicago, IL, US

About This Opportunity

I’m a mom exploring the possibility of launching a microschool for 15-20 students in grades 4-6 to restore my son’s—and other children’s—love of learning. I’m looking for an exceptional educator who dreams of building something transformative from the ground up—someone who wants to be a true co-founder in this venture.

This isn’t a traditional teaching position, and honestly, this isn’t a traditional school launch. I’ve had initial conversations with interested families who share this vision, but I’m being transparent: we’re in the exploration phase. This job posting is about finding the right educator partner to help determine if we can make this dream a reality together.

If you’ve ever imagined what education could look like with smaller classes, full curricular autonomy, and deeply invested families as partners—and you’re willing to take a leap of faith with me—let’s talk.

The Role:
As our Founding Teacher, you would have complete autonomy to design and implement curriculum in collaboration with me and an engaged parent advisory group. Together, we’d create a learning environment that blends the best of Montessori philosophy with experiential, inquiry-based, and problem-solving approaches. While Montessori certification is welcomed, it’s not required—I value innovative thinking and a commitment to student-centered learning above specific credentials.

This is truly a “many hats” role: you’d be educator, curriculum designer, school culture architect, and recruitment partner alongside me and our parent community. You’d help shape every aspect of our school’s identity as we grow together.

Full transparency: This role depends on our ability to recruit enough families to make it financially viable. I’m committed to making this happen, but I need the right educational partner to help bring families on board and build something they can’t resist.

Our Educational Vision:
I’m building a learning community that:
*Embraces experiential and inquiry-based learning: Students learn by doing, questioning, and discovering rather than passive listening
*Prioritizes STEAM integration: Science, technology, engineering, arts, and mathematics woven into meaningful projects and real-world problem-solving
*Values strong literacy: Reading, writing, and communication skills as foundational to all learning
*Cultivates global citizenship: Students develop pride in their own cultural heritage while building genuine respect and curiosity for diverse cultures and perspectives
*Celebrates every child’s identity: Our school would honor and uplift each student’s cultural background, creating an environment where difference is a source of strength.

What I’m Offering
*Compensation: Approximately $70,000 with benefits (contingent on enrollment numbers for tuition-paying students)
*Professional Freedom: Full curricular autonomy with parent advisory consultation

Working Conditions:
*Small class size (15-20 students total across grades 4-6, although we could negotiate the best coupling of ages)
*Highly engaged, supportive parent community
*Collaborative decision-making structure
*Flexibility to innovate and adapt based on what works

Professional Growth:
*Founding team experience that’s invaluable for future educational leadership
*Opportunity to present and share our model as it develops
*Deep partnerships with families in shaping student success

What I bring to the table:
*Passion and commitment to making this happen
*Initial conversations with interested families
*Willingness to handle the business/administrative side alongside you
*A clear vision but openness to shaping it together

Who You Are
You’re an educator who:
*Has experience teaching upper elementary or middle school students
*Thrives with autonomy and takes ownership of outcomes
*Sees small class sizes as an opportunity to truly know and differentiate for each learner
*Believes in students as capable, curious, and competent
*Values authentic partnerships with families and sees parents as educational allies
*Is excited (not overwhelmed) by building something new
*Brings cultural competency and commitment to anti-racist, culturally sustaining pedagogy
*Is comfortable being entrepreneurial—from helping with enrollment to ordering supplies
*Has a genuine passion for experiential and inquiry-based learning
*Embraces the Montessori philosophy of following the child and fostering independence; open to any certification

To Apply, please send us:
*A letter telling us about your educational philosophy and why this opportunity excites you
*Your resume

We can’t wait to meet the educator who will help us bring this vision to life in building a vibrant learning community where every student can thrive!

Morgan Diamond <morganadiamond@gmail.com>