Cruickshank was part of a school's all-male improv comedy group alongside comedians Seth Rogen and Nathan Fielder right before becoming a television personality, putting her comedic skills in use while reporting or interviewing celebrities.

Before joining MTV, Cruickshank was a co-host on YTV for a show called Weird On Wheels along with Mackay Taggart.

Cruickshank has interviewed an array of high-profile people from the pop culture spectrum including the cast of The Hills, The City and the movie Twilight, along with Adam Lambert, Taylor Lautner, Backstreet Boys, Ryan Reynolds, Bill Gates, Zac Efron, Jamie Foxx, Whitney Port, Lauren Conrad.

Cruickshank is now living in Los Angeles, where she filmed a show called Hollywood Survival Guide, which aired on MTV.

Cruickshank played Kristin in The Rest of My Life, a TV movie concluding the ninth season of Degrassi: The Next Generation that aired in Canada on MuchMusic on July 16, 2010, and in the United States on TeenNick.