From left, Michelle Johnston (VP, communications), Jennifer Stewart (founder and CEO), Jake Enwright (executive vice president) and Jennifer Madigan (COO) at Syntax Strategic's 15-year business anniversary held at the Fairmont Château Laurier's La Terrasse on Tuesday, June 17, 2025. Photo by Caroline Phillips
Ottawa business leader Jennifer Stewart recognized by mayor for ‘bold and fearless’ leadership
If you thought yesterday was just another Tuesday, think again. It was officially Syntax Strategic Day in the City of Ottawa, as proclaimed by Mayor Mark Sutcliffe during a reception marking the 15th anniversary of the locally based strategic communications and public affairs agency.
The mayor dropped into the celebration, held on La Terrasse — the outdoor patio at the Fairmont Château Laurier that offers stunning views of the Ottawa River and Parliament Hill.
Sutcliffe set aside his notes and spoke from the heart about the company’s 40-year-old founder and CEO, Jennifer Stewart, with whom he had worked as a business coach before deciding to run for office in 2022. “It’s an honour to be associated with you in any way, and to have played a very, very small part in helping you build this incredible business.”
Mayor Mark Sutcliffe proclaimed June 17, 2025, to be Syntax Strategic Day in the City of Ottawa during a reception hosted by Syntax at the Fairmont Château Laurier’s outdoor patio, La Terrasse. Photo by Caroline Phillips
Sutcliffe first met Stewart at an event when she was still in her 20s. He was immediately impressed. He described how she grew her small business by relentlessly recruiting exceptional talent, making gutsy decisions and attracting top-tier clients — ultimately building a successful company respected throughout the community.
“Entrepreneurs are risk-takers by nature, but I don’t know too many people who are prepared to take as much risk as Jen, who are prepared to be as bold as Jen, who are ready to ensure that their business reflects their values like Jen. That has been a hallmark of everything she’s done.”
Said Sutcliffe: “Jen is bold and fearless, and incredibly brave as a businessperson, but most of all, she is someone who cares about others.”
The mayor hailed the business leader as a “trailblazer” for transforming her workplace to meet her employees’ needs, rather than expecting them to conform to traditional norms. The majority of her staff are women.
“She’s created an environment where people can balance their work with family and other commitments. Because of that, she has been able to attract great talent. It’s a place where employees feel valued and where Jen cares about their lives outside of work, not just the time they spend in the office.”
The official proclamation also recognized Stewart’s dedication as a community builder, one who champions women leadership and who uses her platform to give back, contributing both her time and resources to help local causes (she just joined the board of The Ottawa Hospital Foundation). The mayor capped the moment by hugging Stewart while the crowd clapped and cheered.
Syntax Strategic is behind a five-year, $50,000 partnership with Algonquin College, providing scholarships and paid internships to two students annually to help increase diversity in the public relations field.
The crowd heard brief remarks from two of the interns, Jessica Bell and Anum Saeed, the latter of whom shared how “ecstatic” she was “to be finally offered space for my voice to be heard”.
Mayor Mark Sutcliffe, while speaking to Syntax Strategic founder and CEO Jennifer Stewart, proclaimed June 17, 2025, to be Syntax Strategic Day in the City of Ottawa during a reception hosted by the local business at the Fairmont Château Laurier’s outdoor patio, La Terrasse. Photo by Caroline Phillips
Mayor Mark Sutcliffe with the team from Syntax Strategic at the company’s 15th anniversary reception at the Fairmont Château Laurier’s outdoor patio, La Terrasse. Photo by Caroline Phillips
Stewart also spoke, briefly and without notes. She shared how the milestone anniversary made her pause and reflect — not something that comes naturally to her hustle mindset.
To pay her very first staff member and grow her fledgling business, she withdrew money from her RRSP. It was a tough decision that she made with the support of her husband, Kevin, when she was around 27 and pregnant.
Today, Syntax Strategic has a staff of 24. Along the way, the firm changed its name from JS Communication. Stewart said she didn’t want the business to be “the Me Show”.
“It’s about the team that is here today,” she said, giving a warm and special shout-out to her chief operating officer Jennifer Madigan, who joined her company in early 2017. Madigan, like Stewart, is a graduate of the School of Journalism at Carleton University. Among her previous roles was executive producer of The West Block with Tom Clark at Global News.
Stewart told her colleague and friend: “This business would not be what it is today without your vision, your passion, your dedication, and your growth.”
Attendees included fellow entrepreneur Catherine Clark, with whom Stewart created The Honest Talk podcast and digital media platform for women. The venture also includes their sold-out The Women’s Summit taking place this Oct. 24 at the Brookstreet Hotel. Clark works with Syntax in a strategy role, as well.
The Syntax team also includes executive vice president Jake Enwright, former deputy chief of staff to Erin O’Toole and senior adviser for previous Conservative leaders, as well as vice president of communications Michelle Johnston. She previously worked for the PMO, most recently as deputy director of communications until 2024.
From left, Catherine Clark, president of Catherine Clark Communications, with her The Honest Talk co-founder Jennifer Stewart, founder and CEO of Syntax Strategic, and Michelle Taggart, vice president of planning and development at Tamarack Homes and Tartan Homes, at Syntax Strategic’s 15-year business anniversary held at the Fairmont Château Laurier’s La Terrasse on Tuesday, June 17, 2025. Photo by Caroline Phillips
From left, morning show co-host Ashley Greco (Pure Country 94), Canadian International Trade Tribunal vice-chair Bree Jamieson-Holloway and Mayor Mark Sutcliffe at Syntax Strategic’s 15-year business anniversary held at the Fairmont Chateau’s La Terrasse on Tuesday, June 17, 2025. Photo by Caroline Phillips
From left, Syntax Strategic COO and United Way East Ontario board member Jennifer Madigan with the organization’s vice president of resource development, Mark Taylor, director of communications Andrea Bailey, and chief people officer Heather Dobson, at Syntax Strategic’s 15-year anniversary. Photo by Caroline Phillips
Jennifer Stewart, founder and CEO of Syntax Strategic, delivered brief remarks at her company’s 15-year anniversary reception. Photo by Caroline Phillips
From left, Christie Lake Kids (CLK) manager of corporate sponsorships Reza Mashkoori, BMO Commercial Bank vice president Layla Darwish and her daughter, Carleton University journalism student Alana Darwish, and CLK director of city programs, Amy MacDonald, at Syntax Strategic’s 15-year anniversary. Photo by Caroline Phillips
Jessica Bell, left, and Anum Saeed, both paid interns at Syntax Strategic, are beneficiaries of a five-year, $50,000 commitment that Syntax made with Algonquin College to help increase diversity in the public relations field. Photo by Caroline Phillips
Elevate International president and CEO Solange Tuyishime Keita, left, with Syntax Strategic founder and CEO Jennifer Stewart at Syntax Strategic’s 15-year anniversary reception. Photo by Caroline Phillips
Syntax Strategic hosted a reception at the Fairmont Chateau’s La Terrasse on Tuesday, June 17, 2025 to celebrate the Ottawa company’s 15-year anniversary. Photo by Caroline Phillips
From left, award-winning Altis Recruitment co-founder Kathryn Tremblay and Soula Burrell, director of business development and membership at the Greater Ottawa Home Builders’ Association, at Syntax Strategic’s 15-year business anniversary reception. Photo by Caroline Phillips
From left, Ottawa headshot and personal branding photographer Lindsey Gibeau and Lisa Thibodeau, editor at The Honest Talk, at the 15-year anniversary reception hosted by Syntax Strategic at the Fairmont Château Laurier’s outdoor patio. Photo by Caroline Phillips
From Bell Media/CTV, Todd Hamilton (creative director, English local TV, Eastern Canada) Ashley Greco (Pure Country 94 radio), Jodi Hamilton (operations manager, Bell Media), Peter Angione (director news and information programming) and Joanne Woo (bureau manager) were guests of Syntax Strategic’s 15-year business anniversary reception held Tuesday, June 17, 2025. Photo by Caroline Phillips
Syntax Strategic COO Jennifer Madigan (second from left) and colleagues listened to remarks made at the 15-year anniversary reception of the locally based strategic communications and public affairs agency, held at the Fairmont Chateau’s La Terrasse on Tuesday, June 17, 2025. Photo by Caroline Phillips
From left, CBC Ottawa reporter Celeste Decaire and Anick Losier, chief branding and communications officer at CHEO, were guests of Syntax Strategic’s 15-year business anniversary reception held Tuesday, June 17, 2025. Photo by Caroline Phillips
Jennifer Stewart, founder and CEO of Syntax Strategic, seen hugging her good friend Bree Jamieson-Holloway at her company’s 15-year anniversary reception, held at the Fairmont Château Laurier’s outdoor patio. Photo by Caroline Phillips
From left, entrepreneur and small business advocate Michelle Groulx, LE Strategies business development consultant Liz Ellwood and morning show co-host Ashley Greco (Pure Country 94) at the 15-year anniversary reception hosted by Syntax Strategic at the Fairmont Château Laurier’s outdoor patio. Photo by Caroline Phillips
Stacey McMillan, senior manager at KPMG Canada, at the 15-year anniversary reception hosted by Syntax Strategic at the Fairmont Château Laurier’s outdoor patio. Photo by Caroline Phillips
Buena Grace Dejoode, advisor at Sun Life, and Jason Burggraaf, executive director at Greater Ottawa Homes Builders’ Association, at the 15-year anniversary reception hosted by Syntax Strategic at the Fairmont Château Laurier’s outdoor patio. Photo by Caroline Phillips
From left, Jennifer Madigan, COO at Syntax Strategic, with founder and CEO Jennifer Stewart, at the company’s 15-year anniversary reception held at the Fairmont Château Laurier on Tuesday, June 17, 2025. Photo by Caroline Phillips
Guests mingled on the Fairmont Château Laurier’s outdoor patio, La Terrasse, during the 15-year anniversary party hosted by Syntax Strategic on Tuesday, June 17, 2025. Photo by Caroline Phillips
This article is made possible through sponsorship from Star Motors, WCPD, Marilyn Wilson Dream Properties, ExecHealth, Infinity Convention Centre, Altis Recruitment, Bell Canada, First Avenue Investment Counsel, RBC, Welch LLP, Brazeau Seller Law.
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