Wikipedian-in-Residence (WIR) programs are becoming more common in academic libraries. Although they hold a great deal of promise, they are often limited in scope given their frequently short-term and sometimes part-time nature. After a successful one-year, part-time WIR pilot, the University of Toronto Libraries (UTL) has piloted a one-year, full-time Open Technology Specialist (OTS) role to build upon the WIR’s accomplishments and allow for a more comprehensive approach to Wikimedia activities in the library. Through extensive research, outreach, and relationship-building, the OTS has considerably expanded the scope of WIR’s activities to advance a wide range of institutional strategic priorities for the long term. In line with UTL’s commitment to barrier-free access to all of the right information, the OTS incorporates Wikimedia activities into existing workflows across the library system in ways that prioritize support for historically excluded communities and collections while being sensitive to issues of access and description. In its pilot year, the OTS has created a network out of previously isolated Wikimedia engagement across the library system, trained staff, and volunteers across and beyond UTL, and helped launch formal projects that deepen institutional engagement. The OTS has also continued to contribute to Wikipedia, expanding their editing scope to the appropriate use of archival sources and the development of tools, which help bridge the gap between Wikipedia and Wikidata. Through the OTS, UTL has systematically deepened its contributions to the open Web. The UTL OTS pilot experience has demonstrated that positions dedicated to engagement in Wikimedia or other open technologies hold a great deal of potential and are worthy of further consideration for ongoing investment of staff and budget resources by academic libraries.