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.

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.

Avoid pursuing prosumer and enterprise motions simultaneously. The optimal sequence is to first build massive bottoms-up love and brand trust with individual users. This creates internal champions within target companies, providing crucial momentum and turning a cold B2B sale into a pull-based motion.

Founders whose startups were acquired by large enterprises can become your most powerful internal champions. They understand the startup mentality, know how to navigate internal politics and procurement, and are often motivated to bring in better technology. Actively seek them out.

According to OpenAI's Head of Applications, their enterprise success is directly fueled by their consumer product's ubiquity. When employees already use and trust ChatGPT personally, it dramatically simplifies enterprise deployment, adoption, and training, creating a powerful consumer-led growth loop that traditional B2B companies lack.

1Password's growth illustrates the 'land and expand' model. Start with a B2C product individuals love, which they bring into their workplace. This creates organic internal demand, allowing you to then approach the company with an enterprise solution offering management and compliance.

Enterprise buyers purchase tools like Slack because employees love using them, not based on clear ROI. This presents a major adoption hurdle for non-viral, single-player products like enterprise search, which must find creative ways to generate widespread user adoption and love.

Instead of approaching leaders first, engage end-users to gather 'ammunition' about their daily pains. They may not have buying power, but their firsthand accounts create a powerful internal case (groundswell) that you can then present to management, making the approach much warmer and more relevant.

Your ideal champion inside a large company is often someone who secretly wishes they'd founded a startup but is too risk-averse. They are drawn to the founders' ambition and will advocate for you because they want to feel part of the startup journey vicariously.