Transitioning to virtual (remote) operations creates new challenges stressing traditionally accepted knowledge, motivation, and organizational influences (KMO) for employees and management alike. This study examines how those KMO influencers impact Haven Resource Group’s (HRG) management team’s ability to migrate from 60% virtual operating capacity to 90%. Additionally, this research reviews the practice of external recruiting practitioners and their collective acceptance of virtual technologies and whether their employers are building capacity for technological adaptation. The Clark and Estes (2008) gap analysis served as the conceptual framework for the study with a mixed methods approach using surveys and interviews providing the insights into the organizational understanding of the challenges. The data suggest many employers are not fully committed to capacity building and the transition to a virtual workforce even though employees (a) feel more productive, (b) possess an increased sense of loyalty to their employer when allowed to work remotely, (c) would consider switching jobs if another employer provided a work-from-home (telework) opportunity, and (d) are receptive to receiving training on innovative technologies. To address the identified KMO deficiencies associated with achieving a 90% virtual operating capacity, the study provides recommendations including (a) continuous training on remote technologies, (b) the development of job aids, (c) increased opportunities to work from home, and (d) the adoption of policies, processes, and systems that enable and enhance virtual collaboration and communication.