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.
Contrary to common advice, the biggest companies (Walmart, Tesla) are often the best first customers. They must innovate to maintain their #1 position and are willing to take chances on new tech that gives them a competitive edge or "alpha."
The final stages of a major enterprise deal are often closed via text message, signifying a deep level of trust and personal relationship with the buyer. If your champion isn't comfortable texting you, the relationship may not be strong enough to get the deal across the finish line.
Stop targeting the ambiguous "mid-market." Your strategy, hiring, and ACV must align with either a marketing-led SMB motion or a sales-led enterprise motion. Blending them leads to failure as they are distinctly different games.
Enterprises are comfortable buying services. Sell a service engagement first, powered by your technology on the back end, to get your foot in the door. This builds trust and bypasses procurement hurdles associated with new software. Later, you can transition them to a SaaS product model.
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.
AI outbound tools pull from the same databases, hitting the same people with similar messages. To stand out, go fully manual. Research individuals, send unique, short messages, and target people not in common databases. This "back door" approach is more effective for high-value deals.
At the $1-10M ARR stage, avoid junior reps or VPs from large companies. The ideal first hire can "cosplay a founder"—they sell the vision, craft creative deals, and build trust without a playbook. Consider former founders or deep product experts, even with no formal sales experience.
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.