As academic and cultural heritage institutions increasingly offer digital collections and services, technical upskilling—the process of acquiring and/or expanding technical skills—has moved from an individual prerogative to an institutional imperative. In this publication, the authors share their experiences with, and lessons learned from, a series of four collaborative technical skills development initiatives—the ArchivesSpace-Archivematica-DSpace Workflow Integration Project (2014–2016), a series of Curation Team Workshops (2015), a Technical Skills Pilot Project (2017–2018), and the development of a Bentley Audiovisual Quality Control Utility (2019)—at the University of Michigan Bentley Historical Library. In doing so, the authors advocate for the value of increasing the technical literacy and skills of entire teams/units (as opposed to focusing on the development of individual skills) and provide information and best practices that will enable and empower other institutions to undertake similar initiatives. They conclude by making the case for organizational cultures that value learning together.