In Canada and beyond, employers face challenges in recruiting and retaining staff that have the skills they need. These challenges will only increase as digitization, automation and artificial intelligence change the types of skills employers require. McKinsey estimates that 14% of the global labour force may need to change jobs as technology transforms the nature of work. To change jobs, workers will need to upskill their current skills or reskill in new fields. Yet compared to peers in the Organisation for Economic Co-operation and Development, Canadian employers invest relatively little in training. On average, Canadian employers spent $889 CAD per employee on learning and development from 2016-2017. Yet some employers have begun to recognize the severity of the issue and are taking dramatic action. In a survey of executives at 1,500 large companies, two-thirds said that addressing the skills gap caused by automation and digitization was among the top 10 priorities at their company. Many companies are developing ambitious strategies to reskill and upskill their employees; for instance, Scotiabank has committed to investing $250 million over 10 years to create a highly skilled workforce, while AT&T has invested $1 billion to retrain nearly half its workforce. This report reviews the literature on employers’ efforts to upskill and reskill their employees, and examines the effectiveness and return on investment of various approaches. In addition to corporate programs, it considers three types of investment in reskilling and upskilling: government investment; public-private partnerships, such as Siemens’s partnership with academia and government; and skills training as part of corporate social responsibility and philanthropy, such as the Royal Bank of Canada’s commitment to invest $500 million to help Canadian youth prepare for the jobs of tomorrow. While there is no clear consensus on whether government or corporations should be responsible for upskilling and reskilling, many corporations are taking the lead. Case studies from companies including Amazon, TD Bank, Accenture, and Walmart demonstrate how some organizations have taken small steps by experimenting with pilot programs and new tools, while others have developed comprehensive programs to retrain large segments of their workforce. In some instances, as at Microsoft, these initiatives support both the company and its customers. While companies forge ahead with reskilling and upskilling programs, a lack of empirical data makes it difficult to rigorously determine the success and impact of these programs. Better labour market data, common definitions around skills, and more research to systematically understand the rationale behind corporate investments to reskill, including the return on investment, are needed to better understand and improve reskilling and upskilling initiatives. Further, reskilling and upskilling strategies need to build in performance measurement systems to assess what works and what does not. As digitization continues to shift the type of skills employers need, it will only become more urgent for Canadian companies to understand the impact of reskilling and upskilling programs, and to create a culture of continuous learning to ensure employees have the skills they need.