When selling high-ticket services, don't raise prices incrementally. Instead, make a significant jump (e.g., from $3,800 to $8,000). If it doesn't sell, you've gained valuable market data and can simply re-price the next cohort. The upside of finding a new price ceiling far outweighs the risk of a single failed launch.

Stop trying to convince executives to adopt your priorities. Instead, identify their existing strategic initiatives—often with internal code names—and frame your solution as an accelerator for what they're already sold on doing. This dramatically reduces friction and speeds up deals.

Startup founders often sell visionary upside, but the majority of customers—especially in enterprise—purchase products to avoid pain or reduce risk (e.g., missing revenue targets). GTM messaging should pivot from the "art of the possible" to risk mitigation to resonate more effectively with buyers.

Introduce a significantly more expensive, highly customized version of your service alongside your main offering. This price anchor makes the actual product you want to sell appear like a fantastic deal, even if it has a high price point, thereby increasing conversion rates.

Instead of asking for a budget, which can feel confrontational, state a typical investment range for your solution. This anchors the price, makes the conversation less awkward, and positions you as a transparent consultant by asking where they fall within that range based on their research.

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.

Don't pitch features. The salesperson's role is to use questions to widen the gap between a prospect's current painful reality and their aspirational future. The tension created in this 'buying zone' is what motivates a purchase, not a list of your product's capabilities.

Chasing ten $10k deals over one $100k deal is a mistake. Smaller deals attract clients who nickel-and-dime you, don't fully buy into the vision, and provide distracting feedback. A single large deal provides a committed partner who will help guide your product roadmap.

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.