The Singapore Insurance Employees’ Union (SIEU) has signed agreements with 23 Unionised Insurance companies to facilitate training for workers to prepare them for the digital era in the Insurance Industry. Many have hailed the Employees’ Union for signing the agreement. As Insurance companies globally are embracing big data such as blockchain, Artificial Intelligence and Telematics in their business operations, many have feared that over dependence on these technologies will lead to Job cuts. Insurers however believe that the Industry will still relay on tech savvy employees to survive. The Insurance Employees’ Union is therefore being proactive by facilitating training for Unionised workers to guarantee their Job safety in the digital era.