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Winston Preparatory School

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Winston Preparatory School reviews

3.6

63% would recommend to a friend

(45 total reviews)

62% positive business outlook

Ratings by category

4.0

Culture & values

4.0

Senior management

3.8

Diversity & inclusion

3.6

Work/Life balance

3.6

Career opportunities

3.3

Compensation and benefits

Winston Preparatory School has an employee rating of 3.6 out of 5 stars, based on 45 company reviews on Glassdoor which indicates that most employees have a good working experience there. The Winston Preparatory School employee rating is in line with the average (within 1 standard deviation) for employers within the Education industry (3.7 stars).

Ratings by demographic groups

Reviews by job title

45 reviews
1.0
Nov 7, 2025

A Cautionary Tale

Teacher
Recommend
CEO approval
Business Outlook

Pros

Students are bright, funny, and resilient. They deserve better than here.

Cons

Deeply dysfunctional environment disguised as a progressive private school. Leadership is disorganized, reactive, and unaccountable. Communication, when received, is opaque and often manipulative. Expectations shift constantly. Decisions are made behind closed doors among favorites. Toxicity trickles down from the top. Bullying is tolerated. Many employees quietly admit they stay only for the students. Burnout is inevitable.

4.0
Oct 27, 2025

Chill nice company

Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

Pleasant place to work, 2 months off for summer

Cons

relatively low play, you can negotiate your salary

1.0
Oct 25, 2025

Just Don’t

Teacher
Recommend
CEO approval
Business Outlook

Pros

The kids are the reason I stayed

Cons

Horrible management, rude and aloof. Judgemental and unapproachable. Bring back the old Head of School.

Viewing 1 - 3 of 45 Reviews
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ReviewsWinston Preparatory School reviews

Glassdoor has 47 Winston Preparatory School reviews submitted anonymously by Winston Preparatory School employees. Read employee reviews and ratings on Glassdoor to decide if Winston Preparatory School is right for you.