Project Tomorrow and BrainPOP have collaborated on the development of this new "Education Leadership Brief: Examining the Evolving Digital Responsibilities of School Principals" to examine specifically the evolving digital responsibilities of the school principal today resulting from the sudden shift to digital learning. This examination includes an evaluation of timely Speak Up Research Project data findings and the first-hand insights of principals collected through a series of interviews in February 2021. Principals interviewed included administrators from the Cleveland Metropolitan School District (Ohio), Little Lake City School District (California) and New York City Department of Education (New York). Within the Education Leadership Brief, we discuss four key findings from our research. Each finding includes foundational Speak Up data, front-line perspectives of school principals, and a thought-provoking question for district leadership to consider as they plan for the future. It is our hope that the data and insights shared through this Brief will enlighten and inform new local discussions on how to best support our school principals as they lead a new digital transformation of education at their schools. Key findings include: (1) The Tech-Savvy Principal -- The effectiveness of the school principal as the digital leader on their campus is increasingly dependent upon their own technology skills and knowledge; (2) The Principal as the Digital Instructional Leader -- Being a digital instructional leader means that the principal must role-model appropriately the use of technology to support all aspects of the school experience for teachers, students and families; (3) Principals Are Building Teacher Capacity Using Digital Tools -- Principals recognize that building teacher capacity for using digital tools today will ensure sustainability of these new practices, even when schools are back to full face-to-face instruction; and (4) Principals Envision the Future for their Schools -- Principals see how their changed roles and responsibilities will result in a positive future for their schools, especially relative to the use of technology.