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.

Investor Stacy Brown-Philpot advises that to win large enterprise deals, an AI startup must create a solution so compelling it beats the customer's internal team vying for the same budget. The goal is to access the core 15% budget pool, not the 1% 'play money' budget.

Economist Bernd Hobart argues that large enterprises are too risk-averse for early AI adoption. The winning go-to-market strategy, similar to Stripe's, is for AI-native companies to sell to smaller, agile customers first. They can then grow with these customers, mature their product, and eventually sell the proven solution back to the legacy giants.

AI's capabilities evolve so rapidly that business leaders can't grasp its value, creating a 'legibility gap.' This makes service-heavy, forward-deployed engineering models essential for enterprise AI startups to demonstrate and implement their products, bridging the knowledge gap for customers.

For fragmented, tech-averse industries, GC funds startups to first build an AI automation platform. Then, instead of a difficult sales process, the startup acquires traditional service businesses, implementing its own AI to dramatically boost their margins, providing immediate distribution and data.

Enterprises struggle to get value from AI due to a lack of iterative, data-science expertise. The winning model for AI companies isn't just selling APIs, but embedding "forward deployment" teams of engineers and scientists to co-create solutions, closing the gap between prototype and production value.

Large enterprises don't buy point solutions; they invest in a long-term platform vision. To succeed, build an extensible platform from day one, but lead with a specific, high-value use case as the entry point. This foundational architecture cannot be retrofitted later.

StackAI found the bulk of enterprise revenue comes from expansion, not the initial deal. They operationalized this by creating a team of "AI strategists" who work with customers post-sale to proactively identify and build new use cases, driving deep account penetration and growth.

For enterprise AI, the ultimate growth constraint isn't sales but deployment. A star CEO can sell multi-million dollar contracts, but the "physics of change management" inside large corporations—integrations, training, process redesign—creates a natural rate limit on how quickly revenue can be realized, making 10x year-over-year growth at scale nearly impossible.