Digital libraries (DL) play a crucial role in curating and extending access to unique and diverse cultural heritage materials. Over the last three decades, DL programs have shifted from monolithic, data-centric, and technology-driven operations to more open, user- and service-oriented ventures, built on collaborative relationships. This project set out to explore the challenges and opportunities of the current DL landscape by interviewing DL managers and analyzing websites of six academic libraries in the United States and Canada. The study found DL programs at a nexus, partnering across multiple library functional units, including Special Collections, Information Technology (IT), Technical Services, Public Services, Scholarly Communications, and Administration. The managers deploy collaborative models of leadership within and outside their institutions. They take a proactive role to expand programs and collections, working with faculty in the planning phase of research to attract grants, create accessible content, and foster digital humanities initiatives. Increasingly, they engage in post-custodial arrangements with community partners such as UCLA’s Sinai Library Digitization Project, which brings resources online without seeking to own them. Serving widely different populations, DL managers seek to boost public awareness and access to collections while navigating institutional priorities and chronically tight funding. Quantitative measures from this mixed-method project include data such as the greatly differing size of DL teams and libraries, ranging from 15 to 225 collections. Organizational charts show the variety of operational approaches, while excerpts highlight strategies that DL leaders use to engage with stakeholders to build and promote collections.