The benefits of the gig workforce–also referred to as the contingent workforce–have been well established over the past few years. These benefits range from making hiring easier for hard-to-fill jobs, access to short-supply skills, and more flexible cost structures. And although the number of “gig” workers continues to increase, as does the digital platforms to engage this workforce segment, the ways these workers are hired is often done in an ad-hoc and “transactional” manner versus strategic talent management. If firms are to engage with the on-demand workforce at a strategic level, this article argues that they will need to focus on overcoming five main challenges, two of which include: 1) Reorganizing work into components. Rather than being vague about work, firms need to break work down into rigorously defined components that can easily be transitioned to gig workers. 2) Rewiring organizational policies and processes. Many internal mechanisms and processes for engaging gig workers can be laborious and have unnecessary steps. If companies want to work successfully with digital talent platforms, they need new structures and processes that enable this work rather than present roadblocks. As organizations overcome these five challenges, they can accelerate their ability to leverage the gig workforce in executing business strategy in an agile, cost-effective manner.