Due to the technological disruptions caused by the COVID-19 pandemic, there is a greater demand than ever for people who can operate in a digital economy and have the know-how to adopt and use digital technologies. Yet research and industry surveys consistently reveal that Canada’s digital skills preparedness is falling short. We developed this project to address the call for a better understanding of the digital skills that Canadian businesses need to succeed in an increasingly digital future, as well as the tools and training required to respond to these needs. As a first step, we held 21 key informant industries with executives and upper-level managers at leading Canadian companies, as well as representatives from sector organizations. The goal of these interviews was to hear directly from employers about their digital skills needs, the impacts of COVID-19 on the workplace, and ideas for training/upskilling. Insights from these interviews were used to inform this issue briefing, as well as a larger survey that will be delivered to skills leaders across different industries and regions in Canada. Through this survey we aim to better understand the specific digital skills that are needed and provide recommendations on the tools and training that can help Canadian businesses better prepare for the future.