Jason and his wife Heather live in Oak Ridges, Richmond Hill with their sons Benjamin and Charlie, born in 2014 and 2017.
Jason grew up in Richmond Hill, attending Crosby Heights Public School and Richmond Hill High School. He then went to the University of Toronto, where he earned an Honours Bachelor of Arts with a double major in Ethics, Society and Law, and History. Jason earned his law degree at Dalhousie University in Halifax and became a lawyer in 2006.
In 2008, Jason moved back to Richmond Hill and opened his own law firm, Cherniak Law, in Richmond Hill. He has trained three law students to be lawyers and currently employs two staff. As a lawyer, Jason works with regional and municipal governments across the Greater Toronto Area.
Jason has been on the Board of Directors for the Richmond Hill Board of Trade since 2015. He is the incoming Vice-Chair and the Chair of the Government Affairs Committee. Jason has been active with the Board of Trade on issues ranging from transportation and public transit to small business taxation and municipal governance.
Jason has been an active member of the Rotary Club of Richmond Hill since 2008. As chair of the Rotary TV Auction in its final years, he helped raise over $150,000 for local charities and non-profits. For many years, Jason has been the club lead on a tree planting program on the Oak Ridges Moraine, just off Old Colony Road, where approximately 300 elementary and high school students each year have planted over 12,000 trees.
Jason is also on the board of York Region charity Shadowpath Theatre Productions, the Mackenzie Health Foundation Governance and Nomination Committee and the Corporation of the University of Trinity College at the University of Toronto.