When different departments push their own projects onto the sales team, reps get overloaded. To solve this, enablement leaders must shift the focus of every initiative away from departmental priorities and toward a shared customer outcome. This unified goal minimizes internal friction and clarifies what's truly important.

The difficulty of enterprise procurement is a feature, not a bug. A champion will only expend the immense internal effort to push a deal through if your solution directly unblocks a critical, unavoidable project on their to-do list. Your vision alone is not enough to motivate them.

Visionary founders often try to sell their entire, world-changing vision from day one, which confuses buyers. To gain traction, this grand vision must be broken down into a specific, digestible solution that solves an immediate, painful problem. Repeatable sales come from a narrow focus, not a broad promise.

Enterprise leaders aren't motivated by solving small, specific problems. Founders succeed by "vision casting"—selling a future state or opportunity that gives the buyer a competitive edge ("alpha"). This excites them enough to champion a deal internally.

A common PLG pitfall is assuming the user base will naturally springboard into enterprise deals. Often, the enterprise buyer is a different person with different problems. This oversight can cost companies years, as they have to build a second, separate sales motion from scratch.

A founder's ability to sell is not proof of a scalable business. The real litmus test for repeatability is when a non-founder sales hire can close a deal from start to finish. This signals that the value proposition and process are teachable, which is the first true sign of a scalable go-to-market motion.