The counterintuitive way to sell enterprise software (learned this the hard way)

Background: Spent 6 months cold-pitching executives. Got nowhere.

The revelation: Stop selling up. Start building down.

What I learned:

Build tools that junior employees love but executives will discover and want.

The "Executive Dashboard Trojan":

1. Free tool for individual contributors
2. They create impressive work output
3. Show it in team meetings
4. Executive sees it, demands org access
5. Bottom-up becomes top-down mandate

Why it works:

• Proof beats promises
• Internal champions > external sales
• Organic demand eliminates resistance
• Usage data speaks for itself

Real validation: Datapad's enterprise revenue started this way. Free dashboards → executive presentations → company-wide adoption.

The question: What could you build that junior employees would use daily but executives would want to control?

Anyone else stumbled into bottom-up enterprise sales? What worked?