Syntax Strategic CEO Jennifer Stewart on shaking up the traditional nine-to-five workplace

Ottawa businesswoman promotes family-friendly policies for working moms at all-female communications firm

Editor's Note is supported by the generous patronage of Mark Motors and Marilyn Wilson Dream Properties. Read their stories here.


There were days when Ottawa communications entrepreneur Jennifer Stewart wondered if she’d made a huge mistake by thinking she could juggle business and babies.

Her “mom guilt” would creep in, as it often does with working mothers, leading the president and CEO of Syntax Strategic to question whether she’d taken on too much. But, strength is about staying the course to reach one’s goals, she learned.

Being an entrepreneur has given the 36-year-old working mom more flexibility and freedom to be available for her children when they need her, even if it has meant developing night-owl or early-riser tendencies in order to get work done. It’s helped that her husband, Kevin, a former combat engineer officer in the Canadian Armed Forces, has been tremendously supportive of her career.

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“At the end of the day, what mattered to me was being a good mother, first and foremost,” says Stewart. “Balancing those early years was difficult but I’m really glad I did it. It wasn’t always easy; I had a few moments where I went, ‘What am I doing? Should I have taken this route? Should I backtrack? Is this the right choice?’” says Stewart. “For a few years, there wasn’t a ton of balance, whatsoever, and it was go, go, go.”

Today, Stewart is both a 2017 Forty Under 40 Award recipient and a 2019 Businesswoman of the Year finalist with the Women’s Business Network of the National Capital Region. 

Over the past 11 years, she’s grown Syntax into a profitable company with seven-figure revenues that specializes in strategic communications, public relations, events and branding. Among her clients are Export Development Canada, Native Women’s Association of Canada, FinDev Canada and United Way Centraide Canada.

‘I like being underestimated’

“No day is the same,” says Stewart, who combines her strong communications skills with a passion for business. “Certainly, back when I was in my 20s, as a woman and a blonde, I didn’t always get the benefit of the doubt, but I kind of like being underestimated.

“I love a profit and loss statement. I love a balance sheet. I love forecasting. I love business development.”

Stewart has nearly 15 full-time employees working for Syntax, plus various contractors. That her staff is all women is not intentional, she says.

“I think if the right male candidate came along with the right experience we could absolutely expand, but it has been really neat being a female company.”

Stewart is an Ottawa Valley girl at heart, born and raised in Renfrew. The headquarters for Syntax is located in the west-end rural village of Carp, where she also volunteers her time as board chair of the Village of Carp BIA. She and her family live minutes away in a lovely subdivision home that backs onto wooded walking trails. Her children, Wilson and Maxwell Grace, are nine and seven years old.

As a boss, Stewart is very supportive of working moms. She grew up watching her mother, Jane Wilson, play such a major role in her four kids’ lives while also running her law practice. She made it look so easy, says Stewart, who now realizes it couldn’t have been. By the time Stewart started high school, her mom was appointed to the bench of the Ontario Court of Justice in Renfrew County. 

‘Unnecessary anxiety’

Stewart believes the traditional nine-to-five workplace culture can create an “unnecessary anxiety” among working moms who are trying to balance their jobs with life’s other priorities. Her strategy is to hire the best people and to provide them with a flexible work environment to thrive in. They just have to do their jobs, and do them well, she adds.

“There’s an intrinsic problem with traditional business culture and supporting women. What Syntax has built is shaking that up, and I think so many organizations need to think about retention and about work-life integration.” 

Five things to know about Jennifer Stewart

Stewart is proud of her team, which includes vice president of communications Jennifer Madigan, a former executive producer with Global News, and Michelle Coates-Mather, who has been building the firm’s government relations practice as the VP of strategic, government relations and public affairs. She formerly worked on Parliament Hill and was a director with NATIONAL Public Relations. Her director of brand and marketing, Dana Telfer, was with Senators Sports & Entertainment for many years.

Stewart cultivates a culture where colleagues treat each other as allies, not threats. “If you can’t say something to someone’s face, you don’t say it. I often get asked whether, with that many women in an office, it’s ever catty. It’s really not, to be quite honest with you. It’s actually pretty remarkable.”

Since launching Syntax in 2010, Stewart has made a point of becoming more comfortable with promoting herself and the company. She’s a regular commentator on crisis communications for CTV, CBC and CityNews Ottawa, and regularly writes op-ed pieces.

“For me, it’s not about ego, it’s about driving your business and expertise,” she says. “I think life is too short to be worried about how others perceive us.”

Syntax has fared well during the COVID-19 crisis, but not without great effort. Stewart has been getting up before sunrise, throughout the pandemic, to get started on her workday.

These are busy times for the business, she says.

“We’re coming out stronger than we’ve ever been, but it’s not been through luck; it’s been through strategic conversations, business development and servicing our current client base extremely well.

“It’s been a year of resilience, a year of growth and a year of, honestly, solidifying that this is what I want to do, that this is what I love to do, and that I’m very fortunate to be in this position.

“But, it hasn’t been a breeze.”

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