Prior to the COVID-19 pandemic, the workforce was already facing disruptive changes. The fourth industrial revolution and technology in the workplace, specifically artificial intelligence (AI), robotics, and big data, were already drastically reshaping the profile of a highly skilled worker in the 21st century. Now, the combination of challenges caused COVID-19 and these new workplace technologies are responsible for displacing entire occupations, shifting worker skills and tasks, and creating new sets of skills and tasks (World Economic Forum, 2018b). To ensure full employment of the workforce by 2030, major and possibly historic workforce transitions to new jobs, skills, and occupations will need to occur (McKinsey Global Institute, 2017). Middle skill jobs are jobs that typically require more than a high school diploma but less than a four-year degree. These jobs represent a significantly large sector of the American workforce and have been particularly vulnerable to workplace transitions (Autor, 2015; National Science Board, 2019). In an environment of workforce disruption caused by COVID-19, technology, external market forces, and globalization, middle skills workers need innovative avenues to support adaptation and development of skills for career resilience and sustainability.