Today’s Information and Communication Technologies (ICTs) are designed to address one of society’s most pressing problems—unemployment. These technologies are increasingly hailed as enablers of entrepreneurship and income generation, and they support job seekers’ ability to search for jobs, create resumes, highlight skills, train, and even help transport people to work. However, the benefits of employment tools are unequally distributed and such technologies could reinforce social inequalities. Without an understanding of how those experiencing marginalization and who are unemployed use (or don’t use) ICTs for employment, the same employment inequalities that occur offline will continue in online contexts. In this presentation, I will discuss the results of several efforts to foster innovation and rethink the design of technologies in support of employment, particularly for those who were unemployed before the COVID-19 pandemic. I surface broader issues that impact the employment process such as the digital divide and reimagine employment through entrepreneurship and efforts to build community capacity around digital literacy,