The job of the modern superintendent involves engaging with a variety of stakeholders in meaningful, yet impactful ways. The current study was designed to understand how superintendents leverage technology to engage school level stakeholders (principals, teachers, and students) through technology generally, and about technology integration specifically. Data were collected from interviews with 14 superintendents across the United States. Three themes emerged: collaborating and communicating with stakeholders was vital for stakeholder engagement; providing relevant and timely professional development opportunities for stakeholders was a key lever for stakeholder engagement; and it was essential to nurture a technology-infused learning culture for all stakeholders across the district.