Robert (Bob) Dempsey was born in Stratford, Ontario and culminated his formal education at the University of Western Ontario with a Civil Engineering degree in 1971. He was awarded the James A Vance Medal for the highest standing for the civil engineering graduating class that year.
After a short stint with Bell Canada as a design engineer, he joined the City of Stratford, Ontario as Deputy City Engineer. Subsequently, in 1977, he became County Engineer for the County of Huron until he joined the Guarantee Company of North America in 1987 as Branch Manager of their Woodstock office responsible for Personal Lines and Surety. In 1993, Bob became Senior Vice President in their Toronto office responsible for the Ontario and Maritime Province operations. In 2000, Bob was promoted to Executive Vice President with his responsibilities expanding to include corporate business development in all lines of business. In 2006, Bob was appointed President and Chief Operating Officer of the company working from their Head Office in Toronto.
In 2001 and 2003, the Guarantee Company of North America expanded their operations into the United States of America with the acquisition of two regional surety companies, which Bob is now the President as well.
Bob is a past secretary of the Municipal Engineers Association, past President of the Ontario Good Roads Association, past director of the Ontario Road Builders Association and the Canadian Construction Association. Bob has been a director of the Insurance Bureau of Canada, and is the past President of the International Surety Association. Bob also is appointed to the Credit Insurance Advisory Group for the Department of Foreign Affairs and International Trade. In the past, Bob has also volunteered on various boards and community projects including minor sports, Chambers of Commerce and various hospitals. Bob lives in Aurora, Ontario and in his leisure time enjoys their cottage, grandchildren, golf, bridge and good friends.