Short cycles win. Long shadows and bravado do not close a deal, clarity does. Begin with a quiet room, two chairs, and a whiteboard that stays mostly blank. Ask for the problem in the customer's own language, then ask what hurts most on a Tuesday afternoon when a quota is due or a compliance audit lands without warning. Draw a box around what sits in your control and a separate box around what sits in theirs. Between them, sketch a narrow bridge, only as wide as the smallest realistic proof.
Discovery is a craft of attention. Collect three specifics:
- The workflow step that breaks
- The owner who feels the break
- The cost of that break in hours, dollars, or reputation
Translate each into a candidate success criterion: Not "improve reporting," but "produce the monthly reconciliation in under fifteen minutes with no manual joins." Not "better security," but "pass control 8.3 with evidence generated automatically." Ask for access to representative data and one environment where change will not set off alarms. Promise to tread lightly, then keep the promise.
Proof should be small enough to finish in a sprint and large enough to matter. Define the input, the expected output, and the checker who declares pass or fail. Avoid theatrical demos that hide behind hand-picked samples or muted warnings. Instrument the run. Show logs that a skeptical engineer respects. If an integration is required, prefer a shallow one: a file drop, a webhook, a narrow API path with a clear schema. The aim is not to impress, it is to measure.
Now draw the map from risk to signer. In an enterprise, deals do not die because the technology fails in isolation. They die when a silent risk owner, the keeper of data residency or the steward of identity, sees a surprise in the eleventh hour. Identify those owners early. Give them a memo that names the surface you touch, the data you move, the performance envelope you promise, and the logs you keep. Do not wait to be asked about retention or sub-processors. Bring the answers before the question. When a question falls outside your product's shape, say so plainly and propose a boundary, not a boast.
During the proof, keep a single shared document, visible to both teams, where assumptions are written in ordinary language. Attach a table for blockers, another for decisions, and timestamp each entry so memory does not turn into myth. In the document, record what you tried that did not work and what you changed to make it work. The act of writing becomes the act of aligning. When the proof ends, the document becomes the seed of the contract: services, SLOs, limits, and remedies already named.
Pricing should follow the value and the risk, not a fashion. If your product saves hours, price in a way that turns time into a predictable line item. If it reduces exposure, tie price to the surface area of protection. Offer a small start with a clear ramp, then keep the on"‘ramp short. Volume discounts are not kindness, they are a model of trust: the more weight a customer places on your system, the more you share the efficiency with them. Avoid the temptation to bury fees behind exotic terms. Clean invoices create clean renewals.
Renewals, in truth, begin on day one. Create a cadence where you review outcomes with the customer, not only uptime. Bring charts that show adoption by team and by feature, not just a wall of green. When adoption dips, ask why before you prescribe. Sometimes a small change to defaults unlocks an entire department. Sometimes the right answer is to remove a feature that only you love. The habit of honest review keeps surprises out of procurement and turns an annual rite into a simple continuation.
The final habit is restraint. Do not commit to features that you would not use yourself under the same conditions. Do not grow the scope of the proof when one more inch of scope buys no new certainty. Say where your software stops, and introduce a partner where that boundary makes sense. Resist the theater of the grand reveal. Deals close in daylight: clear outcomes proved in the customer's environment, a map from risk to signer without loose ends, a price that reads like a fair trade, and a shared record of what was promised and what was delivered. Leave the stage to others. Keep the work.
Case notes
Short proofs with explicit success criteria reduce time to value and lower risk for both sides. Teams that adopt shared proof memos borrow a page from modern procurement: decision logs, clear owners, and time"‘boxed tests.