Given the theme of “Pipelines to Prosperity” and the importance of cultivating ongoing practices - as opposed to one-time check-off-the-box-and-it’s-done initiatives – we explore some workplace-tested ideas regarding “what works” based on notions of learning as situated in communities of practice (Lave & Wenger, 1991). To turn these theoretical insights into specific actionable programs, we offer an example of blockchain technology which demonstrates the importance of cultivating agile, diverse, entrepreneurial organizations capable of navigating future landscapes in which learning is a lifelong endeavor. To explore how businesses can reimagine their role in broadening participation in digital literacy initiatives, we draw upon insights garnered from the anthropological lens of “figured worlds” (Holland, Lachicotte, Skinner, and Chain, 1998). This session prepares employers of all sizes to leverage the latest research findings to implement digital literacy practices not only for “knowledge workers,” but for all workers. While Massachusetts is known internationally as a hub of technological innovation, many who hail from historically non-dominant communities, e.g. females, Latinx, Black and Brown individuals, and English Learners (ELs), are underrepresented in industries that require STEM knowledge and skills (Landivar, 2013).The reasons for this are myriad: access to resources is often not enough; successful efforts must also address issues related to identity, i.e. not seeing oneself as a “science person” (Carlone, 2004); the “problematic pipeline” (Chapa & De La Rosa, 2006); and sociopolitical practices that embrace deficiency viewpoints (Gutiérrez, 2013). We frame workplace digital literacy initiatives as one way to improve communication, collaboration, innovation, and actualize increased prosperity for all.