His father established himself as a businessman in the transportation sector in the Uva Province and was appointed Muhandiram by the British colonial administration.
Henry continued his father's business ventures and in 1921 was elected to the Legislative Council representing the Uva Province.
[2] His nephew, Jack Kotelawala, was a LSSP Member of State Council and Parliament and later served as Ambassador to Russia.
His cousin Sir John Kotelawala, served as the third Prime Minister of Ceylon.
Henry married Evelyn Bulathsinhala and they had three children, Gladwin, who served as a Member of Parliament from Buttala, Christobel, who married Oliver Weerasinghe, a leading architect and city planner.