James Bonsey

James Bonsey

Associate Head of School for Finance & Operations

Tabor Academy

James Bonsey joined Tabor in 2023 after serving as the Associate Head of School/Chief Financial & Operating Officer at the Kingsley Montessori School in Boston. During his time at Kingsley, James has overseen several expansion projects and successfully helped the school navigate through the COVID-19 pandemic, including sourcing and opening a temporary third campus to allow the school to return to in-person learning. Prior to Kingsley, James was an Intern Principal at Conservatory Lab Charter School in Brighton, MA and a Social Studies Teacher at Middle Creek High School in Apex, NC. In addition to his professional roles, James is a member of the Board of Trustees at The Cambridge School of Weston in Boston, MA and has previously served as the Board Chairman of Carter Community School in Durham, NC. Prior to his time in education, Bonsey worked in real estate development with firms in Boston, MA; Durham, NC; and London, England.

Online Courses

Past Webinars

  • AI in Independent Schools: Navigating Legal Risks While Embracing Innovation This item is protected

    October 22, 2026
    Artificial intelligence is reshaping independent schools. Explore key legal and risk considerations, including privacy, intellectual property, cybersecurity, discrimination, vendor contracts, and regulation, with practical guidance for policy development.
  • Culture and Compensation: How to Empower Your Faculty This item is protected

    October 9, 2026
    Discover how a school transformed faculty compensation from a traditional salary scale to an innovative banded system. Learn how they secured buy-in, sustained momentum over 9 years, and created a model that supports faculty growth, agency, and feedback.
  • 2026’s Back-to-School Legal & Regulatory Update This item is protected

    September 30, 2026
    Join independent school legal experts as they review recent changes to the law and answer your questions about how they may impact your school.
  • Grants Management for Independent Schools This item is protected

    May 26, 2026
    Designed for business officers who manage or oversee grants, this webinar provides actionable tools and templates to strengthen financial stewardship and enhance mission impact through effective grants administration.
  • Enrollment Forecasting as a Strategic Financial Tool This item is protected

    May 8, 2026
    This webinar presents a strategic approach to enrollment forecasting that blends the enrollment team’s relational insights with financial analysis and data modeling. Learn how to strengthen projections using internal data alongside external signals.

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