[2] Rubinoff attended University of Western Ontario, where he received his Bachelor of Arts degree in political science.
[4] While enrolled as a student, Rubinoff ran as an independent candidate in the London North Centre riding against Joe Fontana during the 1997 federal election.
[1] Rubinoff left his law practice in 2010 so that he could become an associate dean of the visual and performing arts department at Sheridan College.
[4][6] In August 2002, Rubinoff presented his first musical, a local production of A Chorus Line, which played at the Jane Mallett Theatre.
The musical was presented during the time in which Rubinoff finished his articling at Goodman and Carr and being called to the bar in the fall of 2002.
[9] While still practicing as a lawyer, Rubinoff approached Sankoff and Hein with his idea for a musical about the planes that were unexpectedly ordered to land at Gander International Airport following the September 11 attacks.
In 2016, Rubinoff began developing a musical about Norman Bethune, in partnership with Shanghai Dramatic Arts Centre.
[15] While he was an associate dean, Sheridan College transitioned the music theatre performance program from a three-year diploma to a four-year bachelor's degree.
In 2023, Rubinoff was awarded the Meritorious Service Decoration by the governor general of Canada for his work in conceiving and developing the musical, Come from Away.