Dr. Bobb holds a BA(Hons) degree and a Ph. D in Economics from the University of Cambridge. In 1969, he was recruited by the World Bank, through its Young Professionals Program, where he worked as an Economist for several years before taking up an appointment as Deputy Governor of the Central Bank of Trinidad and Tobago in March 1978. He was Governor of the bank from August 1984 to February 1988.

In 1988, Dr. Bobb joined the Inter-American Development Bank in Washington, DC where he served in various capacities, including Chief of Staff to the President.

In 1994, Dr. Bobb was awarded the Chaconia Medal (gold), which is the second highest honour for service to Trinidad and Tobago.

Since November 2008, Dr. Bobb has been a Non-executive Director of The Belize Bank Limited where he also holds the position of  Deputy Chairman. He also chairs Audit Committees of CIHL, The Belize Bank Limited and Belize Bank International Limited.

Dr. Bobb is also the Chairman of the Board of Directors of Methanol Holdings Trinidad Limited.