The Town of Westport, Connecticut is seeking a dynamic and forward-thinking IT Director to lead and modernize its Information Technology operations. Reporting directly to the First Selectwoman, the IT Director will be responsible for the strategic planning, development, and management of the Town’s technology infrastructure, cybersecurity, and digital services across all departments, including public safety, finance, land use, public works, and administration. This full-time, exempt position plays a critical leadership role in driving digital transformation, implementing emerging technologies such as AI, and supporting smart city initiatives that enhance municipal services and operational efficiency.