In 1979, he began his teaching career at () Pittsford Area Schools. Caswell also served as the superintendent of Pittsford Area Schools from 1997 to 2000, retiring in 2000.
In 1979, he began his teaching career at a school district called () Pittsford Area Schools. Caswell also served as the superintendent for Pittsford Area Schools from 1997 to 2000, retiring in 2000.