In 1938, he served as an visiting lecturer at the economics department of the Ceylon University College.
In 1939, he joined the Bank of Ceylon as an accountant and thereafter became the manager of its head office.
In 1950, he joined the newly formed Central Bank of Ceylon as its first Chief Accountant and functioned as head of the banking and currency department.
He did not request an extension to his appointment and retired in 1971 following Finance Minister N. M. Perera's demonetized with the denominations of Rupees 50 and 100 to flush out black money which was done without Tennekoon's knowledge.
He served as Chairman of the Development Finance Corporation of Ceylon from 1974.