[citation needed] In the early 1970s, he frequented the Toronto arts scene, working as an editor of Ski Magazine, and for the ill-fated John Lennon Peace Festival.

[citation needed] Alexander worked at the Global Village Theatre, co-producing late-night shows, along with his marketing and publicity day job at the Toronto Arts Foundation.

[citation needed] He was eventually hired by the Ivanhoe Theater in Chicago, where he met Bernie Sahlins, owner and co-founder of The Second City.

[5] Over the past 42 years, The Second City has operated resident theater and improv training facilities at one time or another in Toronto, Chicago, Detroit, Las Vegas, Los Angeles, Edmonton, London, Ontario, and Cleveland.

Additionally, Alexander expanded The Second City's Training, Touring, and Corporate Services divisions from niche offerings to boutique business lines in their own right.

In February 2016, Alexander announced the opening of The Harold Ramis Film School in Chicago, starting its first term in September 2016.

[citation needed] He has produced movies and television shows with Ed Asner, Dan Aykroyd, James Belushi, Bill Murray, Chris Farley, Bonnie Hunt, Shelley Long, Andrea Martin, Steve Carell, John Candy, Mike Myers, Catherine O'Hara, Harold Ramis, Martin Short, and Dave Thomas.

In 2008, Alexander facilitated a reunion of the cast of SCTV in Toronto, launching The Second City Alumni Fund, which has since raised over $1,000,000 to assist actors and support staff during times of illness or economic hardship.