From 1974 to 1998 Gordon was with McLeod Young Weir and its successors, ScotiaMcLeod and Scotia Capital Markets. He was appointed a director in 1980 and to the Executive Committee in 1983. In 1990, he was appointed President and Chief Operating Officer of ScotiaMcLeod. From 1993 to 1998, he held the positions of Chairman and Chief Executive Officer of ScotiaMcLeod and the successor organization, Scotia Capital Markets.

During his first nine years at McLeod Young Weir, Gordon served in various Fixed Income Trading and Sales capacities. From 1983 to 1990, he headed all Global Fixed Income, Money Market and Foreign Exchange activities of the firm and chaired the firm's Liability Committee. This committee oversaw all capital commitments of the firm in both global debt and equity markets. During this period, he oversaw the expansion of the firm's fixed income activities into the United States, Europe and Asia.

From 1990 to 1998, Gordon's responsibilities included oversight of all the global activities of the firm. These included all Capital Market activities as well as Retail Brokerage, Administration, Investment Banking and Government Finance. He oversaw the creation of Scotia Capital Markets, which combined the capital markets and investment banking activities of the Bank of Nova Scotia and ScotiaMcLeod. This combination produced one of Canada's leading investment banks. During this time, Gordon also served on Scotiabank's Management, Loan Policy and Asset/Liability committees.

In 1998, Gordon joined Altamira Investment Services Inc. as President and Chief Executive Officer. As head of Altamira, one of Canada's largest independent mutual fund companies, he oversaw the restructuring and eventual sale of the company to the National Bank of Canada. After the sale was completed in 2002, Gordon and Steven Sharpe formed a partnership which became Blair Franklin Capital Partners in 2003.

Gordon is a former director of the Canadian Tire Corporation, Orion Capital (a U.S. based property and casualty company which was sold to Royal Sun Alliance Insurance), The Toronto Community Foundation, Canadian Olympic Foundation, Canadian Air Transport and Security Authority, CML Healthcare Inc. and is the former Chairman of the Board of Upper Canada College and of Canadian Tire Bank.

Gordon currently serves on the Board of Max Capital Group Ltd. (a Bermuda-based insurance/reinsurance company listed on NASDAQ), is a director of Canadian Trading and Quotation System Inc., and is Chairman of the Board of the North York General Hospital.