Expert Mode: Rewriting the Unicorn Playbook for an AI-Native World
This article was based on the interview with Jason VandeBoom, Founder & CEO at ActiveCampaign by Greg Kihlström, AI and MarTech keynote speaker for The Agile Brand with Greg Kihlström podcast. Listen to the original episode here:
Every successful enterprise has a playbook. It’s the collection of strategies, principles, and processes that turned an idea into a force in the market. This playbook is honed through years of trial and error, validated by revenue growth, and eventually becomes enshrined as “the way we do things.” It’s a valuable asset, a source of stability, and in times of fundamental technological shifts, it can become a significant liability. The inertia of a winning strategy is a powerful force, making it difficult to question the very foundations that brought you success. Yet, for leaders navigating the current landscape, that is precisely the task at hand.
We are in the midst of one of those fundamental shifts. The rapid maturation of artificial intelligence isn’t just offering a new tool to add to the marketing stack; it’s challenging the core operating models of how we build products, engage customers, and structure our teams. The temptation for established leaders is to treat AI as an enhancement—a feature to be bolted onto existing workflows. This is a safe, incremental approach. It’s also the path to eventual irrelevance. The real opportunity, and the existential threat, lies in understanding the difference between using AI as a feature and rebuilding with AI as a foundation. This requires more than just a technology roadmap; it demands a strategic willingness to dismantle parts of a perfectly functional machine to build a new one, guided by a vision that may seem, to some, unnecessarily disruptive.
The Necessity of a “Semi-Scary” Vision
In a mature organization, decisions are often made by committee, driven by data, and aimed at optimizing a known quantity. This is the hallmark of a well-run scaling operation. However, during a period of transformation, this reliance on consensus can stifle the very innovation needed to break through. To navigate a paradigm shift, you need a counterbalancing force—a voice that is willing to push beyond the comfortable and predictable. Jason VandeBoom argues that this role is not just helpful; it’s essential for survival and differentiation.
“I think it’s critical a business has someone in the business that is that that has fundamental ownership enough of some of the decisions to be able to be the almost outlier in terms of opinionated innovation. Meaning you need someone that’s like borderline people look at them and they’re like, this this person’s kind of crazy. They’re going to destroy the business… if you don’t have someone with enough like ownership of decisions and direction, kind of pushing the boundary to a semi-scary state, it’s almost inevitable where that business goes.”
This is a crucial insight for enterprise leaders. The systems and culture that ensure stability and predictable growth are often the same ones that filter out “semi-scary” ideas. The impulse is to sand down the sharp edges of a truly novel concept until it fits neatly into the existing business model. VandeBoom’s point is that this process of sanitization is where differentiation dies. Whether it’s the founder or another designated leader, there must be an individual or a small group empowered to champion a direction that doesn’t immediately show up in customer feedback surveys or align with established best practices. This isn’t about ignoring the market; it’s about having the conviction to lead it, even if it creates internal tension. In the age of AI, where entirely new ways of solving problems are emerging, the company that waits for its customers to ask for a foundational change will be the one watching a more agile competitor deliver it first.
AI as a Feature vs. AI as a Foundation
The market is currently flooded with “AI-powered” everything. It has become the go-to bullet point on every MarTech website. But as discerning leaders, we know there is a vast difference between a superficial application and a fundamental re-architecture. The former is what VandeBoom calls “bolting on,” an approach that adds a layer of convenience without disrupting the underlying structure. The latter is about rethinking the core user experience from the ground up.
“You don’t change the construct, you don’t materially create any waves in your ecosystem. Nobody’s like truly upset. That means it’s bolted on. And it’s just like, it’s like a a nice little to have… I think if you’re looking to compete with more AI native, if you’re looking to actually be innovative, it has to be more foundational than that. And the best way I could describe that is just if you are changing a construct of how people interact and they find value, that is not bolting on. That’s actually fundamentally changing a construct.”
This distinction is the strategic crux for every marketing leader today. Are you simply using generative AI to write email subject lines faster within the same old campaign builder? Or are you creating a system where the platform autonomously proposes an entire customer journey based on business goals, and the marketer’s role shifts from builder to editor and strategist? The first is a productivity enhancement. The second is a transformation of a core marketing function. VandeBoom’s litmus test is simple and effective: if nobody is upset or even slightly confused, you probably haven’t pushed far enough. True innovation, by definition, changes things. It requires customers, partners, and even internal teams to learn a new way of working. It’s more work and carries more risk, but it’s the only path to creating a durable competitive advantage rather than just keeping pace.
Leading the Human Side of Transformation
A technological transformation is, at its heart, a human one. You can’t simply issue a memo declaring an “AI-first” strategy and expect the organization to pivot. It requires a deliberate approach to leadership, team composition, and, critically, how you frame the change. The goal isn’t to get people to “use more AI”; it’s to deliver better outcomes for customers, with AI as the enabling engine.
“Get to customer value. If you get to customer value, it’s unarguable. Nobody can argue, should we use AI? It’s not about that. It’s like, we are providing faster, better customer value. That’s unarguable. And to get to those points is where I’d say people need to focus first and foremost.”
This focus on outcomes is the key to bringing an organization along. Instead of abstract directives, leaders should champion specific projects that demonstrate tangible benefits. VandeBoom advocates for a “show and tell” approach, where the teams building these new capabilities showcase their successes, creating a compounding effect of inspiration and adoption across the business. This approach also requires a hard look at the leadership team itself. The leaders who excel at optimizing a stable, growing system may not be the ones best suited to navigate a period of disruptive change. The former are masters of the existing playbook; the latter must be comfortable rewriting it. This doesn’t mean a wholesale change, but it does demand a conscious blend of talent and a recognition that the “safe” patterns of the past may be precisely what’s holding the organization back.
The Incumbent’s Advantage
In this new landscape, it’s easy to look at lean, AI-native startups and feel a sense of disadvantage. They have no legacy technology, no established customer expectations to manage, and no existing revenue streams to protect. They can build from a clean slate. While this is a real advantage, VandeBoom offers a compelling counterargument: established businesses possess assets that are incredibly difficult for a startup to replicate. If leveraged correctly, these assets can provide a decisive edge. The key is to fuse the institutional knowledge and data of an incumbent with the innovative mindset of a disruptor.
This is the challenge and opportunity for today’s marketing leaders. The task is not to simply adopt AI but to lead a transformation. It requires nurturing a vision that may feel uncomfortable, making foundational changes instead of superficial additions, and focusing the entire organization on the undeniable gravity of customer value. It’s about having the courage to question the very playbook that led to success, recognizing that the principles of customer focus and innovation that got you here are the same ones that, when applied to a new technological reality, will carry you forward. The game has changed, but for those willing to write new rules, the opportunity is immense.
