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.
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Generic use cases fail to persuade leadership. To get genuine AI investment, build a custom tool that solves a specific, tangible pain point for an executive. An example is an 'AI board member' trained on past feedback to critique board decks before a meeting, making the value undeniable.
Incumbent companies are slowed by the need to retrofit AI into existing processes and tribal knowledge. AI-native startups, however, can build their entire operational model around agent-based, prompt-driven workflows from day one, creating a structural advantage that is difficult for larger companies to copy.
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.
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.
Small firms can outmaneuver large corporations in the AI era by embracing rapid, low-cost experimentation. While enterprises spend millions on specialized PhDs for single use cases, agile companies constantly test new models, learn from failures, and deploy what works to dominate their market.
The true enterprise value of AI lies not in consuming third-party models, but in building internal capabilities to diffuse intelligence throughout the organization. This means creating proprietary "AI factories" rather than just using external tools and admiring others' success.
Jumping to enterprise sales too early is a common founder mistake. Start in the mid-market where accounts have fewer demands. This allows you to perfect the product, build referenceable customers, and learn what's truly needed to win larger, more complex deals later on.
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.
A key competitive advantage wasn't just the user network, but the sophisticated internal tools built for the operations team. Investing early in a flexible, 'drag-and-drop' system for creating complex AI training tasks allowed them to pivot quickly and meet diverse client needs, a capability competitors lacked.
Contrary to the belief that distribution is the new moat, the crucial differentiator in AI is talent. Building a truly exceptional AI product is incredibly nuanced and complex, requiring a rare skill set. The scarcity of people who can build off models in an intelligent, tasteful way is the real technological moat, not just access to data or customers.
