Jay Hennick completed a Bachelor of Arts (B.A.) degree at York University and a Bachelor of Laws (LL.B.) degree at the University of Ottawa. Jay began his career as a corporate lawyer with Fogler, Rubinoff LLP. He worked closely with Lloyd Fogler, the lead partner, and with some of Canada’s leading entrepreneurs as clients.

During the late 1980’s, Hennick sought to establish a company of his own to create wealth for his family. As a teenager, he showed his entrepreneurial spirit by founding Superior Pools – a company that provides lifeguard and services swimming pools for apartments, hotels and residential communities. His investment in and leadership of Superior Pools created the foundation to fund his education and career as a lawyer.

After raising money from family and friends, Hennick established FirstService in 1989. FirstService Corporation, headquartered in Toronto, is in the rapidly growing real estate services sector. Business platforms are: commercial real estate; residential property management and property services. Market-leading brands include Colliers International in commercial real estate; The Continental Group, The Wentworth Group, and The Merit Companies in residential property management and consumer brands Field Assets Services, California Closets, Paul Davis Restoration in property services. FirstService is a diversified real estate services company with more than US$1.5 billion in annual revenues and more than 18,000 employees worldwide.

In 1998, at the age of forty-one, Hennick received Ontario's Entrepreneur of the Year Award for Consumer Services and Canada's Entrepreneur of the Year award for creative service integration. In December 2001, Hennick was named Canada's CEO of the year by Canadian Business Magazine.

Hennick is a Director and Treasurer of The Mount Sinai Hospital and is an active supporter to several charitable organizations. Together with his wife Barbara, he is also founder of The Barbara & Jay Hennick Endowment Fund which contributes monies annually to a variety of causes. On February 6, 2009, Jay and Barbara Hennick gave a $3 million gift to York University's Osgoode Hall Law School and Schulich School of Business to fund the Hennick Centre for Business and Law. The Hennick Centre will promote and develop joint business and law scholarship, education and outreach. Hennick is also the founder and inspiration behind the combined Jay Hennick LL.B.-MBA Programat the University of Ottawa Law School, his alma mater.