Whalen made her presentation TV show appearance in SketchCom in 1998.

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Probably her earliest occupation was planning servings of mixed greens at Cultures in the food court at Square One Mississauga somewhere in the range of 1986 and 1987.

It was during her secondary school years that she fostered an interest in comedy and sketch satire. She likewise picked to be an essayist, entertainer, chief, business visionary, gerontologist, and spy.

She has composed for different TV programs that incorporate SketchCom, The Gavin Crawford Show, The Ron James Show, Instant Star, InSecurity, and The Dating Guy.

— Jennifer whalen (@JenniferWhalen) March 30, 2021

Jennifer composed and created Baroness von Sketch in 2016, with her castmates Meredith MacNeill, Aurora Browne, and Carolyn Taylor which ran until the year 2021.

In 2018, Jennifer won the sixth Canadian Screen Award in the class of “Best Writing in a Variety or Sketch Comedy Series.”

She had once uncovered in a meeting with Women of Influence in February 2018, that she was terminated from The Second City.