A character with no limits
From her unglamorous early gigs to key management roles at CBC and now Twitter, Kirstine Stewart’s drive and trend-spotting talents have made her a media success story
On Halloween weekend 1985, the local Canadian Champion newspaper reported that 24 students at Milton District High School had been honoured as Ontario scholars.
On the list was a shy 16-year-old named Kirstine Stewart, who’d skipped two grades in elementary school but even among older classmates made the academic elite. Even so, few at the school likely would have expected what lay ahead for the music-loving teen.
Now 47, mother of two daughters, happily settled into a second marriage, Kirstine Stewart is media vice-president of North America for Twitter Inc. and has been a controversial attention magnet of the Canadian media world since her short, eventful tour through the CBC.
This fall, her book Our Turn, a how-to for women aiming at executive jobs, was published. It’s a peculiar volume — part memoir, part motivational treatise, part review of the current literature on leadership and technology.
The stylistic shortcomings hardly matter. The book will likely capitalize on the changing times, the advance of women, the opportunities technology provides.
And, of course, on the continuing fascination with its stylish author.
Kirstine Stewart was born to British immigrants to Canada. As a boy in Scotland, her father won a scholarship to an elite academy, a school his mother cleaned. Such circumstances can put powerful pistons on ambition.
After graduating, he enlisted. At a base in England, he met the woman he would marry. In the mid-1960s, the Stewarts came to Canada, where Dad became a mining executive. Kirstine is the elder of their two daughters.
Stewart says she inherited a willingness to take risks from her immigrant parents. “There’s a sense of adventure if you’ve left everything behind and you’re going to something that’s brand new. So I think maybe it’s that sense of adventure I kind of took from them.”
Stewart considered herself something of an outsider in Canada and became an astute observer. “I didn’t figure skate. I didn’t ski. I didn’t play hockey, didn’t watch hockey. So I didn’t do things that regular Canadian kids did. And yet you have to figure out what you do to make yourself part of the team.”
Looking back, she sees that her core strength in her future career was showing itself when she was growing up.
“I used to listen to new releases from Madonna or early Duran Duran and be able to predict which song would be a hit,” she writes in Our Turn. “A few bars in, I could just tell.”
Early on, Stewart’s mother, Marion, conveyed the abiding immigrant lessons that hard work was essential and establishing a foothold was the first order of business.
As a girl, Stewart delivered newspapers, was a cashier, worked in a library and dressed in bonnet and petticoats to play an 1860s farm wife at a local agricultural museum.
Through school, she played flute, saxophone, oboe and clarinet, imagining a future as a composer or conductor.
“I remember my mother looking at me and saying, ‘That’s a hobby. That’s not a career.’ ”
At the University of Toronto, she studied English literature and took some finance courses. By 20, she had a degree, her first apartment, big hair à la1988 and a fiancé.
Stewart had vague notions of a career in publishing. But when an internship in that field fell through, she needed a job.
She opened the classified section of the Toronto Star, where she saw an ad for a “girl Friday” placed by a TV company.
She was about to meet a woman she now regards as the mother of all mentors.
At Paragon Entertainment, Isme Bennie was distributing TV programming from Canada when Stewart came calling.
“All I was looking for was a receptionist, not a brain surgeon,” Bennie, an emigrant from South Africa, told the Star. “That’s how we hired her.”
Stewart arrived at Paragon planning a marriage to Ken Layfield — she was handy enough to make her own wedding dress — and eager to learn.
She was, Bennie says, personable, organized, a quick study. “One day, I heard my receptionist selling programs on the phone,” she recalls. In short order Stewart was on the road, selling with her boss.
They were in Cannes twice a year, in Monte Carlo annually. Bennie gave her a lot of responsibility. And Stewart ran with it.
In 1995, when Bennie left Paragon, Stewart replaced her. In seven years, she’d gone from “girl Friday” to president of a TV distribution company.
A year later, now Kirstine Layfield and living in Burlington, she gave birth to her first daughter.
“She came back to work within a month, because she just couldn’t stand being at home with nobody to talk to,” Bennie says.
Stewart’s first husband was a carpenter. Bennie recalls that Stewart’s parents didn’t approve of the match (or of her second marriage). “Her father wanted a lawyer or a doctor or something.”
Layfield had been laid off from his job. So he stayed home with their daughter while Stewart returned to work. The Layfields had a second daughter on July 1, 2000.
But her career, she writes in Our Turn, became a cause of bitterness. “The higher I rose and the more money I made, the worse our relationship became.”
She left Paragon for Hallmark Entertainment in the U.S. A few years later, she returned to Canada to join Alliance Atlantis and run Home and Garden TV and the Food Network.
There, she was taken with the idea of creating do- mestic stars, using that intuitive sense of what would sell to make celebrities (then and later at the CBC) of Mike Holmes, Debbie Travis and the Designer Guys.
In 2006, she was recruited to join CBCTV as executive director of network programming. In 2010, she was named executive vice-president of CBC’s English-language services.
The experience left scars.
At the CBC, Stewart was accused of dumbing down the network with low-brow reality shows such as Battle of the Blades.
She was accused in gossip media (and it was taken as given by some in-house) of sleeping with George Stroumboulopoulos, one of the stars she made. (She writes in the book that she did not date him.)
She still regrets the fact that, while at CBC, she remained ignorant of the sexual harassment complaints against marquee radio host Jian Ghomeshi, who now faces charges of sexual assault and choking.
As failings go, the inability to ensure a workplace free from abuse was a large one for a woman at the top.
“You would hope that as a woman at the helm, that opens a certain dialogue, a certain openness and ‘Hey, come to me if there’s this issue,’ ” she says. “That didn’t happen.”
During those years, Stewart was widely regarded as icy and aloof.
“Sometimes she’s accused of being cold,” says Isme Bennie. “But it’s not cold; it’s just being private.”
She had a failed marriage, Bennie says. She was a target of scandal sheets. She had daughters to protect. By nature or practice, she keeps a distance, the better to observe, read currents, divine trends.
“All my life, for some reason, I’ve been outside of myself and trying to see where things are moving,” Stewart says.
In 2011, she married Zaib Shaikh, star of CBC’s Little Mosque on the Prairie and now Toronto’s film commissioner. In a world of news and gossip, she kept their marriage secret for several months.
“I’m in love with a person who’s amazingly smart, extremely talented, a person whose sense of ethics and right versus wrong is supremely keen, a game-changer,” Shaikh once told the Star. “I don’t know why you wouldn’t fall in love with someone like that. That’s the person I love. She’s the real deal.”
Two years ago, Stewart shocked Canadian media watchers by leaving CBC to start from scratch at Twitter Canada. She was uninterested, she said, in managing cuts, shrinkage and decline.
The move was a step from a big institution into, well, almost nothing. At Twitter Canada, it was pretty much Stewart and a smartphone to begin. In short order, however, she was vice-president of media for North America, based in New York and responsible for Twitter partnerships in sports, music, entertainment, news and government relations.
As usual, she talked the move over with Isme Bennie. “Kirstine, with all her reserve and everything, is a risk taker, a huge risk taker,” she says.
Only the smallest fraction of women (or men, for that matter) “might have a chance at a Kirstine kind of a career,” notes Bennie. “It’s nice to have someone there as kind of something to strive for, but it’s not an easy thing to achieve.”
In this move, there may have been more risk than even she anticipated.
This year, one of Twitter’s founders, Jack Dorsey, was brought back as CEO. One of his first jobs was to preside over major job cuts to reduce overlap and boost cohesion and focus.
Last month, Twitter stock dropped more than 10 per cent after the company delivered a bleak forecast for its fourth-quarter revenue and profits. Third-quarter results suggested Twitter has not been successful in its bid to attract more users.
Stewart has described her job as being Twitter’s chief evangelist, and in the everchanging world in which she works, the question is always “What can we do with this now?”
Reward, she has found, can come in unexpected ways.
Her mother now suffers from quadriplegia as a result of surgery to remove a brain tumour. To remain connected, Marion tweets.
“She finds in these new communication methods a voice, because she actually physically can’t speak,” Stewart says. “She has a voice and an opinion, and she’s not afraid to express it.
“She uses technology to do that, which I find strangely kind of satisfying, that I get to work in the field which actually makes her life better.”
It must tickle her no end, as well, to see that what Marion Stewart tweets is her pride in her daughter.
“Sometimes she’s accused of being cold. But it’s not cold; it’s just being private.” ISME BENNIE LONGTIME MENTOR AND FRIEND OF STEWART