Jonathan attended the University of Guelph where he received a B.Sc., before being accepted to the Faculty of Dentistry at the University of Western Ontario. Following a year-long hospital internship, he practised as a general dentist in Hamilton. In 2004, Jonathan was accepted to the graduate orthodontic program at the University of Toronto, where he received an M.Sc. in Orthodontics and his Fellowship in the Royal College of Dentists of Canada, Jonathan been practising as a certified orthodontic specialist in the Burlington area since 2006.

Jonathan was then fortunate to be offered a position as a staff orthodontist at the Hospital for Sick Children in Toronto, where he worked for four years caring for children with cleft lip and palate and other craniofacial disorders. He continues to collaborate with the Sick Kids team in his private practice.