Sunday, October 18, 2026

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Westport Public Schools: Help Wanted

If you are an experienced educator and want to work in the administrative area of the Westport public schools system, this may be your time.

As town bodies debate a new education budget that calls for a more than 7 percent increase, the school system has put out the help wanted sign for at least five senior administrative positions, four of which could pay more than $100,000 per year.

“Each position has opened as a result of either a retirement, acceptance of a position in another school district, or reorganization plan as approved by the Board of Education in the past,” Schools Supt. Elliott Landon told WestportNow.

An advertisement appearing in select newspapers this weekend sought an assistant principal at Staples High School with a salary range of $105,251-$112,880; a special education department chair with a salary range of $98,156- $105,249; and a social studies department chair with a salary range of $98,156-$105,249.

Also sought, a guidance department chair with a salary range of $53,138- $97,814, and a vice principal at Bedford Middle School with a salary range of $105,251-$112,880.

Educators have described the market for school administrators as tight, especially in the New York suburban area. 

In addition to an advertisement for the Westport positions, Sunday’s New York Times included ads for similar positions in Norwalk, Poughkeepsie, N.Y., Uniondale, N.Y., and Manhasset, N.Y.

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