In his capacity as Executive Chairman, Gregory is responsible for all mergers and acquisitions in Canada in the employee benefits and pensions sector. In philanthropic circles, Gregory is best known for his role as Chairman of the Duke of Edinburgh’s International Award based in London, UK. He is also a director of Securefact Corporation.
Gregory began his career in insurance in 1981 with Crawford and Company Insurance Adjustors in Atlanta, Georgia, followed by five years at Wellington Insurance Company in Toronto. At the age of 29, he left Wellington to purchase Muntz & Beatty Inc., one of Canada’s oldest commercial insurance brokerages. He was subsequently involved in the acquisition of three more of Canada’s oldest insurance brokerages to form HKMB International Insurance Brokers. HKMB grew to become Canada’s largest privately owned commercial insurance broker which, in 2008, joined HUB International.
During the 1990’s, Gregory became involved with the Duke of Edinburgh’s Award, initially as President of the Ontario Division in 1992, and National President in 1994. In this role, he launched the Charter for Business which, to date, has generated corporate donations exceeding $35 million for “at risk” youth. In 1997, Gregory was appointed a Trustee of the International Award Association; from 2007 to 2015 he served as Chairman of the International Trustees; a position previously held by HRH the Duke of Edinburgh. In 2015, HRH Prince Edward assumed the Chairmanship, Gregory became the Honorary Chairman of the Duke of Edinburgh’s Award World Fellowship. In addition to his position as Chairman of the International Trustees, he served as Chairman of the Business Advisory Group and of the 501c 3 Charitable Trust for the Duke of Edinburgh Awards in the U.S., and is presently a board member of the Duke of Edinburgh’s International USA Award.
Gregory is also a director of the St. Michael’s Hospital Foundation, the Palm Beach Civic Association, The Donnor Canadian Foundation and The Investment Committee for the W.H. Donnor Foundation. His past directorships include the Toronto General Hospital Foundation, the Toronto Insurance Conference, Salt & Light Television and Co-Chairman of the Curators’ Circle Committee at the Art Gallery of Ontario. He is also a heavily involved member of the World Presidents’ Organization (WPO) and was Chairman of the Upper Canada Chapter of the Young Presidents’ Organization (YPO) in 2000/2001.
From 2003 – 2005, Gregory was the first non-American to be appointed Chairman of U.S based Assurex Global, the world’s largest privately held risk management, commercial insurance, and employee benefits group. He served for two terms.
Gregory has numerous national and international awards and recognitions:
- Appointed a Member of the Order of Canada, one of Canada’s highest civilian honours, that recognizes a lifetime of outstanding achievement, dedication to the community and service to the nation (2016)
- Appointed a Commander of the Royal Victorian Order (CVO) by Her Majesty, Queen Elizabeth II (2009)
- The Queen Elizabeth II Diamond Jubilee Medal, awarded to Canadians who build a caring society and country through their service, contribution and achievements (2012)
- Selected by the Government of Canada to welcome new immigrants to Canada by presiding over citizenship ceremonies (2012)
- Knight of the Papal Order, the Equestrian Order of the Holy Sepulchre of Jerusalem, KHS (2006); elevated to Knight Commander (2011)
- YPO Legacy Award granted to YPO members who have overcome great obstacles to achieve success, accomplished something extraordinary in their lives, and/or inspired others (2003)
- The Queen’s Golden Jubilee Medal awarded to those who have made a significant contribution to Canada, to their community and fellow Canadians (2003)
Gregory was born in Toronto, Canada in 1958, was educated at St. Jean Brebeuf Jesuit School and received his Bachelor of Arts degree from Glendon College, York University. He is an active member of the Toronto Golf Club, Granite Club, the Toronto Club, The York Club, the Everglades Club in Palm Beach, The Royal Automobile Club, and Annabel’s in London, UK. He resides in Toronto and Palm Beach, has been married for 29 years and has three children: Scott who works in the insurance business at Lloyds in London; James, a student in Toronto; and Victoria, a graduate student in London, UK.