Singapore, a young and modern city-state in Southeast Asia, is home to more than 5.6 million people, with about 3.5 million Singapore citizens. About 10% or 550,000 of its residents are 65 years old and above, while the country's Total Fertility Rate is rather low at 1.14. Both of these statistical data indicate that Singapore is an increasingly ageing population. Singapore takes on a whole-ofgovernment approach to ensure the country is ready to support seniors and an increasingly ageing population. Legislation and policies are constantly reviewed and changed to help Singaporeans remain employable and employed for longer; numerous health-related programs and initiatives are put in place to ensure active and healthy ageing; and amenities and infrastructure are constantly upgraded to make housing estates and public places more friendly and ready for seniors. Other than legislation, policies, programs and infrastructure, one other important aspect of this whole-ofgovernment approach is the human touch and personal communication. The Pioneer Generation Office (PGO), initially set up in 2014 to reach out to and explain the Singapore government's S$9 billion Pioneer Generation Package, has since expanded its scope of work and objectives to include outreach to, engagement and befriending of all seniors in Singapore. This paper presents a case study of the PGO through the lens of its Chief Training Officer, as she was tasked with overseeing the training, development and readiness of the Pioneer Generation Ambassadors (PGAs) in order to prepare them to carry out their outreach and engagement initiatives to seniors in Singapore.