When testing a new, potentially higher-value customer segment, the single most important data point to validate is revenue retention. Focus initial efforts on confirming that new customers reorder quickly, as this proves the long-term viability and stacking revenue model of the new market.

Since today's AI companies grow too fast to have multi-year renewal data, investors must adapt their diligence. The focus shifts from long-term retention to short-cycle retention and, crucially, deep product engagement. High usage is the best leading indicator of future stickiness and value.

For consumption-based models, simple size-based segmentation (SMB, Enterprise) is insufficient. Stripe and Vercel use a two-axis model: company size (x-axis) and growth potential (y-axis). A small company growing at 200% YoY is more valuable and warrants more sales investment than a large, stagnant one.

High customer churn creates a mathematical limit to growth. By tracking just four key metrics (new customers, churn rate, etc.), you can calculate the exact point in the future where your business will stop growing, forcing you to address retention issues proactively.

A powerful demand signal is when a company repeatedly tries to hire a person for a specific role but fails due to high turnover or an inability to get the job done. This indicates they are willing to spend significant money on the problem and that the human-based solution is flawed, creating a perfect entry point for software.

In every industry, a few established enterprises—like Costco for HR software—act as 'tastemakers' by adopting new technology early. Winning these key accounts first provides crucial validation and influences other companies in the vertical to follow, creating a powerful go-to-market advantage that bypasses smaller customers.

2X CMO Lisa Cole identifies the most potent buying signals as a trifecta: a business catalyst (like new leadership), third-party intent data (e.g., from Demandbase), and first-party engagement (content consumption). The presence of all three indicates a high-probability opportunity.

Instead of broad surveys, interview 10-12 satisfied customers who signed up in the last few months. Their fresh memory of the problem and evaluation phases provides the most accurate insights into why people truly buy your product, allowing you to find patterns and replicate success.

Instead of focusing on traditional sales metrics, one company found its most powerful leading indicator for organic growth was the volume and quality of conversations between its own engineers and its customers' engineers. This metric became the central focus for driving the business forward.