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Strategic Advisory

We help executives lead with confidence and clarity.

At Syntax, we’re hands on. We immerse ourselves in your brand through a fulsome review to deliver meaningful, tailored advice. Whether you’re facing a reputational challenge, entering a new market, developing your personal brand, or shaping your long-term vision, we help you seize opportunities and stay ahead of the curve.

Our approach is grounded in rigorous research, thoughtful analysis, and real-world experience across national politics, top-tier newsrooms, and corporate leadership. From stakeholder mapping and message development to scenario planning and executive positioning, we deliver innovative, actionable counsel that aligns every decision with your mission and protects what matters to you most.

At Syntax, you receive the dedication and care of a small senior team with the perspectives and resources of a larger agency. We embed ourselves in your priorities, offering more than advice.

Decisions define outcomes. Let’s make yours count. Book a call today.


Meet Our Team

Jennifer Stewart
Founder and CEO

Jennifer is an accomplished leader in Canadian business, government, and public affairs. She is renowned as an expert in this field, often being called upon by national media for commentary. Additionally, Jennifer has twice been named one of the “Top 25 People in the Capital” by Ottawa Life Magazine, one of Ottawa’s “Top Forty Under Forty” by the Ottawa Business Journal and the Ottawa Chamber of Commerce, and was a finalist for Ottawa’s “Established Female Entrepreneur of the Year.”

Jennifer has actively taken on many business and community affairs roles, including President & CEO of the Canadian Energy Marketers Association (CEMA), Chair of the Board of the Canadian Transportation Alliance, Co-Host and Co-Founder of The Honest Talk podcast, Chair of the Village of Carp Business Improvement Association (City of Ottawa), Board Member of the Youth Services Bureau of Ottawa Foundation, Member of the Board of Trustees for The Women in Technology Scholarship of Willis College, and Member of the Leadership Council of the Ottawa Regional Cancer Foundation.

Jennifer Madigan
Chief Operating Officer

A communications and media relations professional with a long history in the TV and online news industry, Jennifer has a Bachelor of Journalism with combined Honours in Sociology from Carleton University. Over nearly 15 years in TV news, Jennifer worked as a reporter, videographer, and producer locally, and later as the Executive Producer of The West Block with Tom Clark on Global News.

During the years, Jennifer has gained a great understanding of the media maze and possesses a keen ability to spot and solve problems during a crisis. She also knows how to tell a story with impact. Jennifer uses these skills to help clients effectively shape and communicate their narratives. Jennifer provides strategic communications advice, crisis communications and media relations support, as well as media training for a list of clients including Crown corporations, national associations, and non-governmental organizations.

Jake Enwright
Strategic Counsel – Associate

Jake is a public affairs strategist with 13 years of government and public relations experience. Previously working in the fast-paced, highly visible setting of Parliament Hill, Jake has a proven track record of success managing communications for large organizations that earn significant media attention and has held senior roles advising cabinet ministers and corporate leaders. Jake’s areas of specialization include strategic communications, media relations, crisis communications, government relations, and ghostwriting.

Jake continues to be actively involved in federal politics and previously served as the Deputy Chief of Staff to the former Leader of the Official Opposition, Erin O’Toole. Jake also worked as a senior advisor and media spokesperson for former Conservative Leader Rona Ambrose, and the former Minister of Industry James Moore. He has been consistently recognized by the Hill Times as one of the top political staffers in federal politics and is often asked to contribute political commentary for national media outlets.

Michelle Johnston
Vice President, Communications

Michelle has built a career as a trusted communications advisor at the highest levels by providing strategic and tactical advice on issues that demand both nuance and clarity. Before joining Syntax, she spent over a decade helping senior government leaders make complex decisions and communicate with confidence. Her steady leadership helped governments reach key audiences, keep their message on track, and cut through the noise. As a former Deputy Director of Communications to Prime Minister Justin Trudeau and senior advisor to cabinet ministers across Parliament Hill and Queen’s Park, she has an insider’s understanding of how political actors get things done.

Whether navigating policy intricacies, crafting compelling narratives, or managing crises, Michelle delivers thanks to her extensive experience in policy development, communications strategy, media relations, and issues management. Michelle holds a Bachelor of Arts in History and Political Science from the University of Toronto.

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