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.
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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.
SaaS companies scale revenue not by adjusting price points, but by creating distinct packages for different segments. The same core software can be sold for vastly different amounts to enterprise versus mid-market clients by packaging features, services, and support to match their perceived value and needs.
Frame every negotiation around four core business drivers. Offer discounts not as concessions, but as payments for the customer giving you something valuable: more volume, faster cash payments, a longer contract commitment, or a predictable closing date. This shifts the conversation from haggling to a structured, collaborative process.
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.
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.
Don't let your personal perception of what's 'expensive' limit your earning potential. Set your price high based on the value you provide. It is easy to lower a price that gets no buyers, but impossible to know if you could have charged more if you start too low. Never say no for the customer.
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.
Jumping to enterprise sales too early is a common founder mistake. Start in the mid-market where accounts have fewer demands. This allows you to perfect the product, build referenceable customers, and learn what's truly needed to win larger, more complex deals later on.
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.
Instead of hiding price until the end of the sales cycle, be transparent from the start. Acknowledge if your solution is at the high end of the market and provide a realistic price range based on their environment. This allows you to quickly qualify out buyers with misaligned budgets, saving your most valuable asset: time.