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Leo was the Chief Financial Officer of the Workers’ Compensation Board (WCB) of Nova Scotia until he retired in 2020. As Chief Financial Officer, he was responsible for all administration, technology and infrastructure, investments and financial affairs of the WCB and its 400 employees. Leo also oversaw an annual operating budget of $300 million, an investment portfolio of more than $1.3 billion, and $1.9 billion in benefits liabilities. Leo served as the Chief Financial Officer since 1996. In that time, the WCB has improved its overall funding position by more than 25 per cent.

Previously, Leo served as an auditor and management consultant with a major public accounting firm, and also spent part of his management career with a major Canadian restaurant franchisor. He also volunteered with a number of community groups and has served as the Chair of the Board of Directors of Halifax Public Libraries.

Leo was appointed to the Public Service Superannuation Plan Trustee Inc. in 2013 and he also served as Chair of its Investment Committee.