Kirstine Stewart's big career shift in 2016 shows bold moves can be the best

The Diply executive (formerly of Twitter, and the CBC) on the value of brash career moves

Kirstine Stewart is no stranger to big career changes. Back in 2013, she quit a plum job as executive vice-president of CBC’s English-language services to join Twitter, then a company of fewer than 1,000 employees, where Stewart would act as head of Canadian operations sans office or co-workers.

Stewart has called leaving the CBC (where she was the youngest person and the only woman to ever hold her position) one of the boldest, smartest employment decisions she’s ever made. But three years later, the media maven made headlines again with a career move far riskier than the last.

Stewart admits she had never even heard of Diply GoViral before the company approached her this summer with an offer to become its first chief strategy officer. “I had to Google them,” she says. Her search unveiled a new media business based in London, Ont., mostly known for creating and aggregating clickbait content: kitten-themed listicles, makeup hacks and so-called epic fails. Not, perhaps, the most natural move for a woman once responsible for such highbrow fare as The National, who also, after being promoted to Twitter’s vice-president of North American media in 2014, often shared a stage with the likes of Justin Trudeau.

But Stewart was looking for a change. In fact, she was out of work, having recently decided to leave Twitter. “I was thinking, OK, I’ve accomplished these things, and now I’m looking for something different,” she explains. While the professional restlessness wasn’t new for Stewart (in a Medium post she wrote on the topic of her departure, she referenced a pattern of churning through jobs every three years), the way she acted on it was: She quit with no opportunity lined up. “It seems pretty presumptuous to leave something without knowing where you are going next,” she says. “But I realized there was a huge risk of not going anywhere at all.”

Stewart found the up-and-leave approach both liberating and apprising. Her high profile and very public departure from Twitter meant a lot of people were interested in talking. She started taking meetings, but the process felt different than the last time. “Instead of being singularly focused on my next move, I was listening to each offer that was coming at me,” she says. “I was opening myself up to what else was out there.”

Unsurprisingly, Stewart was courted by several traditional media outlets, but she wasn’t interested in doing more of the same. She found herself drawn to the idea of joining a more entrepreneurial environment, maybe a founder-run company that was growing fast and seeking direction. “I found I really wanted to help a business move forward,” she says. And that’s when Diply called.

Founded in 2013, Diply claims to reach 150 million monthly unique viewers and has called itself the fastest-growing website in history. But that is not what caught Stewart’s attention. She sees Diply’s nimble, more-is-more ethos as perfect for a media landscape in which audiences expect to both interact with and create content. And after meeting with founders Taylor Ablitt and Dean Elkholy, Stewart discovered an opportunity to do something new to her: to shepherd a scrappy upstart through the process of becoming something potentially massive. The prospect was exhilarating.

As strategy lead, her role is to manage growth while keeping Ablitt and Elkholy from spreading themselves too thin. “I hope to help them determine the best future path,” she explains, “but keep it flexible, given that nobody can predict the future.” It’s an idea that aptly sums up Stewart’s own unorthodox career trajectory. “A lot of people get caught with their goal being so defined that it’s tied to a specific role,” she explains. “You need to know well enough where things are moving to know where your values and skills fit in best.”