The world of Fortune 500 executives is a small, interconnected community. Rather than casting a wide marketing net, focus all energy on securing one key 'lighthouse' customer. Over-deliver value for them, even if the deal isn't profitable. Their endorsement and introductions to peers are more effective than any marketing channel.

Employees at large companies who independently work nights and weekends on projects outside the roadmap, driven by customer obsession, are exhibiting the key traits of a founder. This behavior, while potentially disruptive to their team, signals a strong, innate entrepreneurial drive ready to be unleashed.

Most SaaS startups begin with SMBs for faster sales cycles. Nexla did the opposite, targeting complex enterprise problems from day one. This forced them to build a deeply capable platform that could later be simplified for smaller customers, rather than trying to scale up an SMB solution.

For a new product, don't choose between targeting executives or end-users; do both simultaneously. While mapping the C-suite (top-down), engage lower-level employees to gather intel and build internal champions (bottom-up). This dual approach creates pressure and relevance from both directions.

Pursuing large "whale" customers for early validation is risky because they often come with heavy demands that can derail the product vision. Instead, seek out innovative, mid-level companies who are early adopters. They provide better feedback, and building traction with them opens doors to larger clients later.

At the $1-10M ARR stage, avoid junior reps or VPs from large companies. The ideal first hire can "cosplay a founder"—they sell the vision, craft creative deals, and build trust without a playbook. Consider former founders or deep product experts, even with no formal sales experience.

Blippar found that large, established companies wanted to fit new tech into old media silos (e.g., play a TV ad on a print ad). In contrast, challenger brands like Juice Burst were dream clients. Their risk appetite and hunger for an edge made them willing to experiment and create truly innovative use cases.

In initial meetings with enterprise prospects, Nexla's founder didn't pitch a solution. He focused entirely on validating the problem. By asking, "Do you see this problem as well?" he framed the conversation as a collaborative exploration, which disarmed prospects and led to more honest, insightful discussions.