The Winsor School is a diverse, vibrant community that values intellectual curiosity, authentic engagement and personal integrity. We challenge our students to lead lives of purpose as responsible, generous-minded women. The school is committed to employing faculty, staff and administrators who serve as educational leaders in our learning community and who will strive to uphold the school’s mission: to prepare young women to pursue their aspirations and contribute to the world. To support and promote Winsor’s longstanding commitment to diversity, candidates of color are encouraged to apply. 
    • Meet our Teachers: Lisa Stringfellow

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  • Faculty and Staff Workshops, Conferences, and Meetings

    Winsor is committed to supporting a community that models engagement and lifelong learning. We encourage our faculty and staff participate in a wide range of professional development opportunities annually. Some of our most often participated opportunities include but are not limited to the following: 

    • SEED (Seeking Education Equity and Diversity), workshops on combating racism and increasing inclusivity in schools especially. Faculty and staff meet monthly, with readings. 
    • WACR (White Allies Challenging Racism), a Winsor group started over 10 years ago, meets 2x/semester, with readings.
    • POCC (People of Color Conference), annual NAIS 4-day conference, co-scheduled with SDLC (Student Diversity Leadership Conference), Winsor sends the maximum allowable student participants annually. 
    • Diversity Directions Conference and other summer DEI workshops for educators
    • Ongoing trips to National Museum of African American Culture and History in Washington DC: 2x/year, groups of 10 faculty/staff (5 groups so far)

    This year, our faculty and staff have focused on diversity, equity, and inclusion work including:

    • March 2020 faculty/staff meeting: reviewed employee diversity and equity survey data and qualitative responses (from fall 2019 survey) 
    • August 2019 faculty/staff workshop on equity: Facing History facilitated difficult conversations around identity and politics; internal facilitation on LGBTQ+ identity and support
    • August 2018 faculty/staff workshop on difficult conversations: Stanley King Institute facilitated
    • March 2016 faculty/staff workshop on equity: internally facilitated, case-study format

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  • Recent Summer Reading Selections for Faculty & Staff

    Each summer, the faculty and staff read at least one required book related to diversity, equity, and inclusion practices, and often a second book focused on pedagogy and innovation.  Readings form the foundation for focused professional development, invited speakers, and conversations, all of which underscore Winsor's commitment to lifelong learning.  Here is a sample list of recent books that have inspired us.

    2019 The Person You Mean to Be Dolly Chugh
    and Make It Stick: The Science of Successful Learning by Peter C. Brown, Henry L. Roediger III, and Mark A. McDaniel

    2018 The Hate You Give by Angie Thomas and The Girl at the Baggage Claim: Explaining the East-West Culture by Gish Jen

    2017 Blindspot: Hidden Biases of Good People Mahzarin Banaji and Anthony Greenwald

    2016 Just Mercy: A Story of Justice and Redemption by Bryan Stevenson

    2015 Whistling Vivaldi: How Stereotypes Affect Us and What We Can Do by Claude M. Steele

    2014 Thinking About Difference: The Professional Approach to Diversity in Schools, Independent School Magazine, Summer 2014

    2013 Covering: The Hidden Assault on Our Civil Rights
    by Kenji Yoshino

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  • 13

    Average Class Size
  • 7:1

    Student-Teacher Ratio
  • 60+

    Towns Represented
  • 50%

    National Merit scholars
  • 83%

    Faculty with advanced degrees
  • 21 Years

    Median Faculty Tenure

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  • Apply for a position

    If you are interested in applying for a current opening at The Winsor School, scroll to the bottom of this career page and fill out the application linked to the advertised position.
     
    If you are not applying for a specific position but are interested in being considered for a future opening, please fill out an Application for Employment.


  • Benefits at a glance

    • medical, dental and vision
    • 100% employer paid life insurance, and long term disability insurance
    • health savings account, and flexible savings account
    • paid time off, and paid medical family leave 403(b)
    • retirement plan with 5% to 10% employer contribution
    • sabbatical program, professional development fund, and the Virginia Wing Summer Grant Program
    • lunch provided by Flik
    • commuter benefits, and parking subsidy
  • Location of the Winsor School

    The Winsor School is located in one of the most vibrant neighborhoods in Boston, known for its restaurants, retail, academic institutions, and the Longwood Medical area. Home to Fenway Park, the area also boasts proximity to the Museum of Fine Arts, the Isabella Stewart Gardner Museum, and downtown Boston.  Winsor is a short walk to Brookline and to an abundance of green spaces, from the Muddy River to the Emerald Necklace and many parks in between.  The Fenway neighborhood is accessible via the Green Line, bus routes, and by car.