When launching a new product, err on the side of a higher price. This strategy provides the flexibility to reduce prices later if needed—a much easier maneuver than attempting significant price increases on an established user base. As one advisor noted, 'it doesn't take a genius to reduce prices.'

Many founders delay pricing discussions until Series A, but this is a mistake. Establishing a commercial model and value capture strategy from the pre-seed stage is crucial. If you don't charge appropriately from the start, you train your early customers to undervalue your product, making it harder to scale monetization later.

Prospects who haven't bought your type of solution in a long time lack proper context. They will compare your modern, high-value offering to a cheaper, older, or simpler alternative they understand, leading to sticker shock unless you proactively reframe their perspective.

A low price can signal a low-quality or immature product, repelling enterprise or mid-market customers. Raising prices can make your product appear more robust and suitable for their needs, thus increasing demand from a more desirable—and previously inaccessible—market segment.

When entering an established market, use competitor data to set a premium price point. This lets you test the market's tolerance. If conversion is low, you can test lower prices, but it's much harder to raise prices after launching too low.

Affluent buyers use price as a filter for quality. If your product is priced too low for the value it claims to provide, they won't believe it works and will choose a more expensive competitor. Raising prices can counterintuitively increase conversion rates by signaling confidence and quality.

Selling a small, cheap "land" deal to an enterprise customer is dangerous. When you try to expand, they will question the 10x price jump, making it nearly indefensible. Start with a price ($75k-$150k) that reflects enterprise value to avoid being trapped by a low initial anchor.

Your product might feel expensive in a vacuum. To combat this, introduce a VIP or high-end option priced 3-5x higher than your main offering. This use of price anchoring makes the standard option appear much more reasonable and approachable by comparison, similar to how a $200 steak makes a $30 steak look like a bargain.

Contrary to the belief that top-tier products sell themselves, even OpenAI—the hottest company on Earth—uses pilots for major deals. If your pilots aren't converting, the issue is your product's value proposition, not the pilot process itself.