Connections and Confidence: How Jennifer Stewart built a successful communications firm before turning 40

Like many aspiring reporters, when Jennifer Stewart graduated from Carleton University’s Journalism program she took a gig at a rural publication to get her feet wet. For Jennifer, that meant moving into a small boathouse which didn’t even have a lock on the door, and immersing herself in the world of reporting at the Huntsville Forester. “I spent a lot of time walking around town with a notepad in my hand,” she says, “and I forged some really strong connections.” While she was still considering law school or teachers’ college as alternative career paths, she says she loved what she was doing too much to divert her focus just yet.

Twelve years later, with countless accolades (Ottawa’s Forty Under 40 awards in 2017, Top 25 Influencer in Ottawa by Ottawa Life Magazine and a finalist for Ottawa’s Female Entrepreneur of the Year) and a highly successful communications business under her belt, it’s clear that Jennifer made the right decision.

From journalism, Jennifer transitioned seamlessly into PR and government relations. “Thanks to a connection I made in Huntsville, I was offered a job with Enterprise Canada, a public affairs firm in Toronto,” Jennifer recalls. “While my boyfriend (now husband) was on tour in Afghanistan and unreachable at the time, I made the decision to move, knowing he’d be supportive.”

Jennifer says she found her first true mentor in Enterprise’s CEO, Barbara Fox. “She probably doesn’t even know she was a mentor to me in the traditional sense, but in watching her, journalistically taking her in, I learned so much.”

When the military relocated her husband to Petawawa, she got a communications job in Ottawa, providing her insight into what she didn’t want to do for the rest of her life. “I found that working for someone else wasn’t for me, and that the priority should be on the work, versus hours in your chair. I left that job and started down my own path.”

Taking that leap began an entrepreneurial journey that would result in the formation of Syntax Strategic, Jennifer’s internationally recognized communications and business strategy firm servicing the technology, petroleum, energy, and healthcare sectors, among others. “When I started out on my own, initially as a freelancer, I remember thinking, how am I going to compete in such a crowded marketplace? It took a lot of hustle and long hours.”

With a ‘fake it until you make it’ attitude, Jennifer set out to prove herself — something she’d been doing her entire career.

Working from her home office in the early days, Jennifer joined many relevant organizations, attended networking events, sat on the board of Ottawa’s branch of the International Association of Business Communicators, and very quickly established a name for herself in the community.

At 27, she gave birth to her son. Her husband had finished his military service, and he took paternity leave so she could continue growing her business. She got pregnant again just a few months later, had a daughter, and continued to work without missing a beat.

“I wouldn’t be where I am today without the support of my husband,” Jennifer says. “He’s fantastic and ambitious in his own right — in fact, we’ve just taken on a grain and barley export business together — and he’s always pushed me and been all-in when it comes to running Syntax.”  

Today, Syntax has a staff of seven — who happen to be all female — plus a roster of contractors and service providers, giving Jennifer a team of 15 to 20 individuals working for and on the business at any given time. She’s focused on running an agency that’s inclusive, supportive, and turns out the highest quality work. “I have really high expectations of my team, but it’s not about having butts in chairs for long hours every day — that’s the type of environment I left behind in my last job,” she says. She respects that everyone has personal and professional priorities to balance, and knows that a happy, motivated team will garner the best results.  

“The key to success is hiring people who aren’t just putting out product, but rather embodying the same work ethic, vision, and commitment to the process which I have — who share a sense of ownership,” she says. “I treat my team and I expect that in return. And as a result, these are the individuals who will help catapult us to the next level; we’re all in this together.”

Syntax’s clients include Export Development Canada (EDC), Algonquins of Ontario, and Federation of Canadian Municipalities, to name a few, and projects marry media relations, strategic communications, and government relations.  

As Jennifer prepares to move her team into the new building she’s just purchased in Carp — a growing agricultural village west of Ottawa, where she lives and sits as chair of the local Business Improvement Area — she looks forward to what’s to come. “I would like to be the Arlene Dickinson of Communications 2.0,” she says. “Too many women are afraid to say what they want, for fear that it won’t happen, but you can’t be afraid to put it out there — there’s nothing wrong with being ambitious.”

At the helm of a thriving business, plus a second business she’s running with her husband, and with great things on the horizon, Jennifer says that at the end of the day her number one priority remains her children. “If all this went away tomorrow, I’d still have my family,” she says. “But I want to show my kids, that while I’m not perfect, I am a good mom, and a strong business person. And I love what I do.”