You spent more than a decade working in marketing at Google, rising to head of marketing for Canada. How would you describe Google’s culture and its approach to innovation?

Unlike organizations that push innovation through rigid, top-down plans, Google’s foundation was more like a university or research lab. It encouraged small ideas to sprout and grow across the company, with minimal bureaucracy. Other companies might hesitate due to the ‘strategy tax’ that often comes with such a free-flowing approach, but Google embraced it.

It was perfectly acceptable to have multiple, even competing, visions of the future — think YouTube versus Google Play Music. While this certainly had its challenges, especially in complex areas like Android with numerous partnerships, Google’s ultimate belief was clear: True innovation is what users decide works best for them. You had to allow all ideas to compete, letting the best approach naturally win out.

This philosophy resonates even more powerfully today, particularly as AI has drastically lowered the cost of product development and ideation. With so much disruption unfolding, a centralized, top-down view simply cannot reliably predict what’s next. A thoughtfully managed "ideas from everywhere" approach isn’t just beneficial; it’s the most effective strategy to navigate our rapidly evolving market.

From old-school analogue approaches to the latest digital tools, you have said that “every marketing lever can still work in the right context.” Please explain.

The absolute prerequisite for success in today’s marketing landscape is attention. In a ‘distraction economy’ where people are overwhelmed by content, ads, entertainment and their own daily demands, the first obstacle is achieving breakthrough. This is a concept we used to measure years ago in CPG [consumer package goods] marketing. Back then, fewer channels meant you could almost guarantee eyeballs. Today, that is far from the truth. However, the encouraging reality is that for every tactic and every channel, you can still find individuals who are deeply engaged with specific content. What truly matters is creating something so compelling and contextually relevant that it genuinely resonates with that person at that precise moment and in that particular place. That might take the form of a powerful experiential event, a truly memorable Super Bowl ad, or even a genuinely helpful chatbot. When executed correctly, every single tactic can still connect and drive meaningful performance.

The real challenge is figuring out how to produce deeply relevant marketing consistently for all channels and users — at scale and quickly. Understanding how and when to deploy each tactic, and critically, accurately measuring its true impact, becomes paramount. This leads to my personal marketing pet peeve: Because every tactic can contribute, marketers often fall into the trap of trying to be everywhere. They develop plans to be on every platform, mistakenly believing that simply adapting content across channels is the same as achieving a true breakthrough within each. This results in what I’ve called a "landscape of sameness," where quality is unfortunately sacrificed for quantity.

The true strategic advantage today comes from prioritization. We need marketing plans that explicitly identify where we’re not showing up — and more importantly, why.

You have described your marketing philosophy as having three pillars: moments that matter, metrics that matter, and spending time on what matters. Please unpack that for us.

Google championed the phrase “moments that matter,” and that has always stayed with me. You need to show up in critical moments along the path to purchase to even have a chance as a marketer. Where I tried to extend that with my teams is to understand the metrics that related specifically to the moment, and the tactics that will drive the most impact. In effect, you get those three essential pillars: moments that matter, metrics that matter and spending time on what matters. It’s a framework for prioritizing impact over mere activity. Together, these pillars ensure that marketing investments are pragmatic, strategy-led and, ultimately, effective.

You have talked about the importance of bringing joy to customers — and actually using joy as a metric. How is this best achieved, and how can joy be measured?

In a marketing landscape increasingly defined by sameness and what often feels like AI-generated content devoid of soul, fostering genuine emotion — specifically, joy — becomes a critical differentiator. If you make someone feel joyful, they gravitate to you. In marketing, I believe this is the emotion that will break through more than anything. My guess is that this is precisely why we’ve seen such significant growth in experiential marketing and events recently. Most online content and advertisements struggle to stand out, suffering from a lack of originality. Events, however, offer a real opportunity to make someone feel something impactful. It is in these moments that genuine connection is forged, providing a stark contrast to the superficiality prevalent elsewhere. This ability to evoke true feeling is bringing marketers back to these tactics in droves.

As for measurement, while joy isn’t a standalone KPI [key performance indicator], its impact can be observed through metrics that indicate deep engagement and memorable experiences. We look beyond basic impressions to indicators like sustained brand advocacy, increased word-of-mouth, social sentiment analysis for emotional resonance and direct behavioural outcomes tied to positive brand interactions. It’s about measuring the qualitative shift in perception and loyalty that comes from making people feel genuinely seen and valued, ultimately translating into stronger brand affinity and, yes, business performance.

You transitioned from working for one of the world’s largest tech companies to founding an AI start-up. How did you come up with the idea for 99Ravens?

The birth of 99Ravens came from my deep frustration that AI wasn’t solving what I saw as the real marketing problem. Campaigns typically don’t fail from a lack of sheer output. Ten thousand AI taglines won’t save a flawed strategy. Instead, the real Achilles heel in marketing is often the ‘broken telephone’ effect — that critical loss of strategic intent during handoffs.

I recall an $80-million Gen Z campaign where, despite immense effort, we discovered the media plan had veered entirely off strategy. The core problem? A lack of genuine dialogue and clear briefs that became diluted. I founded 99Ravens to directly address these strategic fault lines: the points where original strategy gets lost, the constant battles CMOs face to maintain global alignment, and the reliance on expensive consultants because expertise simply can’t scale.

Our initial thought was to build a “Grammarly for Briefs” to ensure solid foundations. But we quickly understood that true strategic brilliance isn’t about a single perfect brief; it’s about integrating multiple, expert perspectives seamlessly. This led to our fundamental pivot: using AI to amplify — rather than replace — human expertise.

We’re developing AI agents designed to codify the “strategic signature” of proven leaders — effectively allowing teams to tap into the strategic mindsets of their CMOs [chief marketing officers] or CSOs [chief strategy officers] on demand. Our mission is to transform that invaluable, often siloed, human knowledge into scalable, actionable systems that democratize strategic thinking and eliminate the inefficiencies plaguing enterprise marketing.

If part of your company’s vision is that AI should amplify human ingenuity rather than replace it, talk a bit more about how this applies to the marketing realm.

The idea that AI should amplify human ingenuity, not replace it, is the bedrock of our vision and my entire philosophy. This applies directly to marketing strategy because of the prevailing easy button mentality — whereby AI is used predominantly for automation to churn out more content faster. In my experience, most AI automation leads to a dangerous trade-off: We end up sacrificing strategic depth for sheer volume, creating a deluge of uninspiring sameness where generic, derivative content fails to stand out.

Especially today, campaigns succeed because they are saying something compelling and operating off true consumer understanding — not just flooding the zone. In my opinion then, AI’s true potential isn’t in helping us do more average work; it’s in enabling us to do better breakthrough work. We must move beyond viewing AI as a tactical execution tool and embrace it as a strategic accelerator.

"Anything but artificial" isn’t just our tagline, it’s our guiding principle. We believe good marketing is more art than science, and no algorithm can replace the spark of human ingenuity or the vision that sets great campaigns apart. AI’s role is to enhance what strategists, creatives and planners are capable of, automating the repetitive tasks that bog them down while keeping human creativity at the core of every strategy. This ensures that technology serves strategy — not the other way around — ultimately delivering true differentiation and impact in a crowded market.

Creative industries are facing fundamental disruption from AI. What can marketing, advertising and other creative professionals do to remain relevant amidst all the disruption?

People will remain relevant amid AI by doing less of what AI is currently hyped for, and more of what only humans can do. It’s easy to get caught up in the PR spin from AI builders, but frankly, we’re not even in the “first inning” of AI. The stadium hasn’t been built yet — we don’t even have the permits. Marketers need to ignore what people say they’re doing with AI and instead focus on running their own race. The evidence is clear that around 95 per cent of AI pilots are failing. In my estimation, this is because non-expert marketers are building AI models that spit out content that looks right but lacks true strategic depth. The real expertise, the strategic depth, comes from the last five per cent of context and human expertise. That last five per cent is what makes a strategy relevant, the nuance that elevates a creative idea, or the critical internal data point that unlocks a solution. The hard part of marketing isn’t just executing; it’s finding that unique insight that truly solves the brief, not just fills it.

To remain relevant, professionals must double down on this last five per cent. They should focus on what makes them great and use AI not to replace that ingenuity, but to codify it in a way that a) they own; their unique strategic signature; b) they can share and scale, making their expertise accessible to their teams and clients; and c) keeps them in control, ensuring strategic choices remain firmly human-led.

What does best-in-class marketing look like at this moment in time?

Best-in-class marketing today isn’t about being everywhere; it’s about being deeply relevant where it truly matters. We have more channels and tactics than we know what to do with, yet the most effective marketing feels truly bespoke to a specific channel, tactic and, most importantly, to a user.

The best marketing now is often brand marketing, just scaled. It manifests in long-form content that might be too in-depth for a casual observer but is profoundly engaging and resonates with the right audience. It’s often niche and ‘inside baseball’ to outsiders, but for the target audience, it sparks that crucial feeling of, ‘Wow, they really get it."

The marketers who will win in this next phase will ignore the standard playbooks for media and creative. They’ll start with a truly amazing, human-led idea, then use strategic playbooks and AI to scale and distribute it. If you’re starting by optimizing for algorithms, you’ve already failed.

This article originally appeared in the winter 2026 issue of the Rotman Management magazine.