Derby school staffers are among the highest paid in the city Eddy Martinez FacebookTwitterEmail 1of5 Superintendent of Schools Matthew Conway was the highest paid employee in Derby in 2020.Ned Gerard / Hearst Connecticut MediaShow MoreShow Less 2of5 Principal Jennifer Olson earned $151,864.56 in 2020, making her the third highest paid educator in the district.Contributed photo - Derby Public Schools /Show MoreShow Less 3of5 4of5 Principal Mario Ciccarini leads the annual Bradley Elementary School Halloween Parade in 2019. Ciccarini made $146,202.78 in 2020, putting him fourth on the list of h...