Digital Strategists · Educators · AI Consultants
A pattern repeats every decade or so. A new technology arrives, and suddenly organizations that are thoughtful, capable, and doing meaningful work find themselves trying to communicate in a world that has already changed. The tools continue to evolve faster than the messaging, and the gap between intention and understanding grows.
We started Jester to close that gap. We have 30+ years of experience working through several major technology shifts from the early web to social media to mobile and now AI. We help mission-driven organizations adapt, stay relevant, and communicate their value with clarity in every new era.
— OUR STORY
Built from 30+ years at the intersection of strategy, technology, and change.
Jester was founded in 2003, when blogging was new, and Facebook didn't yet exist. From the beginning, Jester was built around a belief: that the organizations doing the most important work are often challenged with communicating it.
Over more than two decades, that belief has been tested through our engagements with hundreds of organizations. We have helped colleges, charities, government agencies, associations, and growing businesses. The work has evolved, but the core premise hasn't: How do we help our clients tell better stories?
The real question about AI has never been whether we will use it. The real question is how we choose to use it, and, just as important, who we trust to help guide the way.
AI strategy is not a pivot for us. It is a natural extension of work we've always done: helping organizations understand and act on change before it acts on them. When AI emerged as the defining operational and communications challenge of this era, we were already in the room.
Today, Jester sits at a rare intersection: we are strategists, practitioners, and educators. We deliver keynotes and workshops across Canada and the U.S. We develop AI roadmaps for leadership teams and help them implement strategies that are responsible and ethical. And we still do the digital marketing and communications work that started it all because strategy without execution is just a slide deck.
— OUR TIMELINE
Some businesses start with a plan. Ours started with a friendship.
Jester’s founders (Sue and Jen) are best friends first and business partners second, and that foundation shapes everything we do. Over the years, we have shared ideas, challenged each other’s thinking, and refined what it means to communicate with clarity and purpose in a world that is constantly changing..
2003
Jester founded
One of Canada’s first full-service digital creative and marketing agencies.
2008
Social media & training expansion
Early leader in social media marketing training for SMBs, higher education, government, and non-profits.
2012
Strategic communications focus
Deepened practice in higher education, government, and tech sectors.
2017
National advisory work
Expanded consulting practice across Canada, including several federal engagements.
2024
AI integration practice launched
AI strategy is formalized as a core service for mission-driven organizations.
2026
Clarity Compass launched
Launch of Jester’s AI readiness assessment tool, built for sector-specific contexts.
— WHAT DRIVES US
Not principles on a poster.
This is how we actually work.
Most digital marketing consultants don't teach. Most AI consultants don't have 30+ years of sector experience. Most educators don't deliver implementation work. Our intersection is unusual, and it's what sets Jester apart from other digital companies.
These aren't aspirational statements. They're the commitments that shape every engagement, from how we scope a project to how we deliver and implement.
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We don't give template answers. Every engagement starts with developing an understanding of your specific situation, including the culture and the constraints that make your organization different.
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Academic frameworks matter, but only if they produce something your team can actually act on. We translate emerging technology into decisions and steps, not white papers that sit on a shelf.
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We'll tell you when your strategy has a gap, when your timeline is unrealistic, or when the tool you're excited about doesn't fit your context. You are paying for honesty, not smoke and mirrors.
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Efficiency is a means, not an end. We help you adopt AI when necessary and improve operations in ways that serve your mission and your people.
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Every AI implementation has a human dimension, from staff anxiety and culture change to trust and acceptance. We design for people, not just processes.
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We're not going to deliver a report and disappear. The organizations we work with best are the ones we stay close to through iterations, pivots, and the unexpected.
What our clients say
“We contracted Jester to present an in-person workshop to our Marketing and Communications Division on incorporating brand journalism into our marketing efforts. Working with Jester was a very smooth process, and she accommodated our tight schedule, including customizing segments of the training to meet our specific needs.”
Elizabeth Braitenbach
Manager, Communications, Tourism Saskatchewan
“Jester has been an indispensable resource for me: helping to design my website, advising on its evolution over many years, maintaining and updating the site... It has always been both reassuring and comforting to know that they were available, even on short notice, to lend their expertise, professionalism, and helping hands.”
David J. Mitchell
Former CEO of the Public Policy Forum
“If you're looking for exceptional services, look no further than Jester. They are a pleasure to work with. They went above and beyond to ensure a seamless redesign process, with swift and adept responses to my questions. I'm delighted with the new CEPSM website. Kudos to their brilliance!”
Mike Kujawski
President, Centre of Excellence for Public Sector Marketing
— WORKING TOGETHER
Let's talk about where your organization is headed.
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45 min - No pitch deck, just a conversation
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4 min AI readiness assessment - free
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