Cheng Wai Keung holds the positions of chairman and managing director of property, lifestyle and investment company Wing Tai Holdings. Founded in 1955 in Hong Kong, Wing Tai was incorporated in Singapore in August 1963 and listed on the Singapore Stock Exchange in 1989. Its assets exceed SG$4.5 billion.

In 2019, a good class bungalow on an 84,543 sqft freehold site in the Nassim area made the headlines when it was sold by a private company owned by Cheng and his wife for a record SG$230 million. The existing site incorporates a full-sized tennis court and an in-ground swimming pool. The Chengs had first put the property on the market in 2013, with an asking price of around SG$250 to 300 million.

The deputy chairman of Temasek Holdings and vice-chairman of the Singapore-Suzhou Township Development is also the chairman of Singapore Health Services, a director of the Kidney Dialysis Foundation and an adviser to Sumitomo Mitsui Banking Corporation Singapore.