Career Opportunities

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Dedicated, passionate, and professional teachers are the heart of Deerfield-Windsor School.

We hire passionate and talented educators to offer a rich and engaging curriculum, preparing our students to be lifelong learners while fulfilling our mission to develop students for college and for life. In our smaller, focused learning environment our students are guided by teachers and coaches who know them and can recognize when they need a boost or a challenge.

Deerfield-Windsor supports its teachers’ commitments to lifelong learning. We value continuing education opportunities and assist our faculty in expanding their areas of expertise. Sample opportunities include:

  • Attendance at national and local conferences
  • Workshops (one-day to one-week) during the year and summer
  • Independent school conferences
  • Virtual training and conferences


Deerfield-Windsor offers a comprehensive benefits package to eligible employees that includes medical, dental, retirement plan matching, life insurance, long term disability, and tuition remission.

  • Benefits concierge and claims advocacy
  • Robust medical plans, including a HSA option
  • Health Reimbursement Arrangement (HRA)
  • Dental plan
  • Basic and voluntary life insurance and AD&D
  • Long term disability
  • Telemedicine
  • Voluntary vision plan
  • Employee Assistance Program (EAP)
  • Retiree benefit program

In order to provide equal employment and advancement opportunities to all individuals, employment decisions at Deerfield-Windsor School will be based on merit, qualifications, and abilities. Deerfield-Windsor School does not discriminate in employment opportunities or practices on the basis of age, race religion, color, handicap, sex, physical condition, developmental disability, sexual orientation or national origin, or any other characteristic protected by law.



ADDITIONAL BENEFITS INFORMATION: This link leads to the machine-readable files that are made available in response to the federal Transparency in Coverage Rule and includes negotiated service rates and out-of-network allowed amounts between health plans and healthcare providers. The machine readable files are formatted to allow researchers, regulators, and application developers to more easily access and analyze data.