Product as a Trojan Horse

The New Gates of Troy

For centuries, the city of Troy stood as an impregnable fortress. Its walls were high, its gates were guarded, and its leaders were the sole arbiters of who—and what—was allowed inside. For decades, the world of enterprise software resembled those ancient walls. To sell a product to a large corporation was to lay siege to a fortress. The process involved a small army of salespeople, months of strategic planning, and a relentless campaign aimed directly at the kings of the castle: the CIO, the CTO, and the CEO. The goal was to convince these powerful gatekeepers to sign a massive, top-down contract that would impose the new software upon their entire kingdom of employees. It was a slow, expensive, and brutal form of warfare. Victory, when achieved, was absolute. A single signature could mean millions in revenue and thousands of users overnight. But the landscape of this war was built on a fundamental assumption: that the leaders at the top knew what was best for the workers at the bottom. The software they chose was often clunky, complex, and despised by the very people forced to use it. It was designed to solve organizational problems, to check boxes on a security audit, or to integrate with legacy systems—often at the expense of the user’s sanity and productivity. The employees, the foot soldiers in this corporate kingdom, had no say. They used what they were given. Then, quietly, a new strategy began to emerge. It was subtle, almost invisible at first. It didn’t involve a frontal assault on the C-suite. It didn’t require lavish dinners with executives or armies of salespeople. Instead, it targeted the unguarded side entrances, the forgotten pathways into the city. This new strategy was embodied in a new kind of product, one that looked less like a battering ram and more like a gift. This was the Trojan Horse. Companies like Dropbox, Slack, and Evernote didn’t ask for a meeting with the CIO. They didn’t need one. Their target was a single, frustrated employee. Someone who just needed to share a file that was too large for email. A small team of developers tired of being buried in endless reply-all chains. A project manager desperate to organize their notes without using a spreadsheet. These products offered a simple, elegant solution to a personal, painful problem. And crucially, they offered it for free. Like the fabled wooden horse left at the gates of Troy, these tools appeared harmless, even helpful. An employee would discover Dropbox and start using it to store their own files. They’d find it so useful that they’d share a folder with a colleague to collaborate on a project. That colleague would sign up, and then share it with another. The same pattern repeated with Slack. A small team, fed up with inefficient communication, would create a free workspace. They’d invite a few more people. Soon, conversations that once cluttered inboxes were happening in channels, visible, searchable, and far more efficient. The product wasn’t being sold; it was spreading. It was an infection of efficiency, a virus of productivity. This is the essence of the Product as a Trojan Horse strategy. It bypasses the traditional gatekeepers by appealing directly to the end-user. It weaponizes user delight and individual utility to gain a foothold inside an organization. It doesn't ask for permission; it earns its place through value. The product itself becomes the primary driver of acquisition, adoption, and expansion. This is the core of what we now call Product-Led Growth (PLG), a movement that has fundamentally reshaped the software industry. While the old guards were busy reinforcing the main gates—perfecting their enterprise sales pitches and security checklists—an entire generation of software companies was quietly rolling their horses up to the walls. By the time the CIOs and IT departments noticed, it was often too late. The product wasn't just inside the gates; it was deeply embedded in the daily workflows of their most productive teams. The employees weren't just users; they were advocates. They were champions. And they were making it clear that taking this new tool away would be a declaration of war on their own productivity. The choice for leadership was no longer whether to let the horse in, but how to gracefully pay for the army that had already conquered the city from within.