Lee served in command and staff positions in the Singapore Armed Forces and held the rank of Brigadier-General. After leaving the military, he joined SingTel in April 1994 as the Executive Vice President of Local Services. In May 1995, he became its Chief Executive Officer and held this appointment until March 2007. He was replaced by Chua Sock Koong, SingTel's financial chief, on 1 April 2007. In September 2007, Fraser and Neave appointed Lee as a Non-Executive Director and Chairman-Designate with effect from 6 September 2007. Lee assumed the position of Non-Executive Chairman of the Company and Consultant on 15 October 2007. On 1 July 2009, Lee was appointed as the Chairman of the restructured Civil Aviation Authority of Singapore by Singapore's Transport MinisterRaymond Lim. On 26 February 2013, it was announced that Lee had stepped down from the board of Fraser and Neave. Lee has held other positions such as: Board Member and Chairman of the Audit Committee of the Singapore Exchange; Independent Director of the Islamic Bank of Asia and the Australian & New Zealand Banking Group ; Member of the Governing Board of the Lee Kuan Yew School of Public Policy; Member of the Board of Asia Pacific Investment; Chairman of Republic Polytechnic; Member of Rolls-Royce Holdings's international advisory board. Lee once said in 2006 that he has "no great interest to pursue a career in politics." He later joined the Progress Singapore Party in 2020, citing that the PAP has lost its way, it is no longer the PAP of its founding principles that Mr Lee Kuan Yew had envisioned. Lee stepped down as Chairman of CAAS on 1 July 2018. He is succeeded by Mr Edmund Cheng Wai Wing.
Lee is the younger son and youngest child of former Prime Minister of Singapore, Lee Kuan Yew and Kwa Geok Choo. His elder brother, Lee Hsien Loong, is the current Prime Minister. His elder sister, Lee Wei Ling, is a former director of the National Neuroscience Institute. Lee is married to lawyer Lim Suet Fern, the daughter of economist Lim Chong Yah. She is the founder and managing partner of Stamford Law Corporation and a former president of the Inter-Pacific Bar Association. The couple have three sons: Li Shengwu, Li Huanwu, and Li Shaowu. Their eldest son, Li Shengwu, is currently serving as Assistant Professor in Economics at Harvard University. He graduated from Balliol College of the University of Oxford as the top student in the Philosophy, Politics and Economics programme in 2009., with a MPhil degree in Economics from Oxford in 2011, and a PhD degree from Stanford University in 2016. Li Huanwu came out as gay in July 2018. He married his partner, Heng Yirui, in South Africa on 24 May 2019.
Administrator of Lee Kuan Yew's will
Lee and his sister, Lee Wei Ling, are the joint administrators and executors of Lee Kuan Yew's will. However, they were in a dispute in 2017 with Lee Hsien Loong over their late father's will with regard to the house at 38 Oxley Road. They "felt threatened by Lee Hsien Loong's misuse of his position and influence over the Singapore government and its agencies to drive his personal agenda". They alleged that their brother thwarted the will of their father in order to use the house as a monument to milk his father's legacy. They also criticised the influence of the first lady Ho Ching over the government, and alleged that the Prime Minister harboured political ambitions for his son, Li Hongyi. A special parliamentary session was held to clear the Prime Minister of any wrongdoings and the siblings agreed to keep the dispute private after the session.