Director of Compliance

Aaron Bailey


Aaron Bailey

Mr. Aaron Bailey is a regulatory hacker and Director of Compliance at Higher Ground Education. He is responsible for our organization’s interactions with government regulatory agencies and the rules they enforce. His work is to ensure that schools can open on time, in a predictable manner, and with minimal regulatory interference with our operations. Child care and education regulations were not written with Montessori programs in mind, so Mr. Bailey finds ways to make our programs compliant without compromising our values or core pedagogy.

Mr. Bailey received his BA from Biola University. He has worked complex litigation before over half the U.S. Circuit Courts of Appeal and the California Supreme Court and has been heavily involved in bleeding-edge constitutional civil rights litigation.

My Story

Learn more about Aaron.

  • What inspires your work?

    I get involved in projects very early in the expansion process, and I’m the last step in the school open process. This means I get to see our campuses when they’re just an empty building, and when they’re fully complete and ready to open. When I do my job right, it enables our schools to open on time and remain open without untoward interference. I absolutely love what I do.

    Nothing inspires me more than seeing a busy school full of engaged staff and happy students learning and knowing I helped make that possible.

  • How did you discover Higher Ground Education?

    My wife began teaching in a Montessori school years ago, and through her I met the team that would become Higher Ground. I joined the company very early on to license our first set of schools and have been building out our compliance capabilities ever since.

  • How does your work inspire your daily life? How does your daily life inspire your work?

    I’m incredibly lucky to be doing what I love and loving what I do. I used to do this sort of regulatory hacking for fun as a volunteer in my free time, and now I get to do it as a profession. I try to bring that hacker attitude – the creativity, the sense of adventure, the willingness to take risks and try new things – to my home life and my professional life.

  • What have you learned during your time at Higher Ground thus far?

    Where to begin? I’ve learned how to work in a closely-knit team on a basis of trust and mutual respect, a customer service-oriented approach to litigation and risk management, and so much about Montessori education.

  • What do you enjoy most about working with your teammates?

    The Higher Ground team is such a rare and inspiring group of people to work with. The level of personal ownership, dedication to mission, extreme competence, and camaraderie I’ve found here is beyond compare.

  • What are your passions, interests, and hobbies?

    Spending time with my family, civil rights advocacy, constitutional litigation, and precision rifle target shooting.

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