AI-Assisted Sales

Most of the work that loses you deals is not the selling. It is the connective tissue: reading the lead, pulling the case study, drafting the reply, logging it, setting the reminder. Hand that to a system that runs at three in the morning and your scarce humans show up only where judgement is required. But there is a deadlier trap. A demo books a pilot, the pilot earns a logo, the logo raises a round, and a signature got counted as revenue. A pilot is branded curiosity, not a contract. The core move: design every pilot with a written success bar and a path to paid before it starts.

The method

Map where money moves, automate the middleware, and gate every pilot to paid. Full framework: references/sales-motion.md, drawn from handbook Chapter 11.

Step 1: Map the path a dollar takes

Write the real sequence from first contact to signed and supported, the way it happens today. Mark each step with one word: where an agent helps, and where a human must stay.

Step 2: Draw the line and automate one step

Everything below the trust line runs as software; everything above it stays a person. Automate the single step that is most repetitive, most often where deals go cold, and lowest-risk to hand off. That one step is your first revenue agent, not the whole pipeline.

Step 3: Design the pilot with the bar set first

Before the pilot starts, write the success metric, the timebox, and the path to paid. No open-ended pilots. Use the pilot-design template in the reference.

Step 4: Build the buyer's gate map

On day one, ask the champion who in procurement, security, and compliance must sign, and where each stands today. A pilot with all three mapped and moving is a deal. A thrilled champion and three blanks is a press release waiting to expire.

Step 5: Put the human gate at the send, and the money

Route, qualify, gather, log, and schedule unattended. Keep a human on the act that touches your name: the message going out and the money going out. An agent that drafts is a force multiplier; one that issues a refund to the wrong account is a liability that bills you.

Output

• A sales-motion map: the real stages, with each marked human or middleware, and the one step automated first.
• A pilot-design template filled for one live pilot: success metric, timebox, path to paid, gate map.
• The pilot-to-paid gate: pilots and contracts in separate columns, with conversion tracked as its own number.
• Next: stand up the routing spine with gateway-agent-ops, then capture-learning on the first pilot result.

Constraints

• Name the failure mode: the open-ended pilot with no success metric. A pilot without a written bar and a path to paid is where deals go to look alive while they die. Forbid it.
• Apply human-on-the-loop: automate the middleware, never the decision to trust a vendor or release a budget, and never automate spam. The human gate sits at the send and the money.
• Stay theme-agnostic; the founder supplies the domain and the real buyer. Never invent a customer, a pilot result, or a figure.

Dictionary

gateway agent · decoupling headcount from revenue · the six-pillar trust substrate · data flywheel

Copy-paste version

For non-coders: paste into any chatbot or no-code builder (Claude.ai, ChatGPT, Lovable, Bolt, v0). Tag: build.

Act as my AI-native revenue-operations architect. Product: [ONE_LINER]. For: [ICP]. Domain:
[DOMAIN]. My riskiest live pilot: [PILOT]. My binding limit: [CONSTRAINT].

1. Map the real path a dollar takes, first contact to signed and supported, as it happens today.
   Mark each step HUMAN (the call, the close, the trust) or MIDDLEWARE (routing, summarising,
   drafting, logging). Tell me how much of my sales day is middleware in disguise.
2. Circle the ONE middleware step to automate first: most repetitive, most often where deals go
   cold, lowest-risk to hand off. That is my first revenue agent. Do not automate the whole pipeline.
3. Design my pilot with the bar set BEFORE it starts: the one success metric that converts to a
   yes, a fixed end date, and the exact contract terms a pass triggers. No open-ended pilots.
4. Build my buyer's gate map: name who in procurement, security, and compliance must sign, and ask
   me where each stands today. Tell me which blanks make this a press release, not a deal.
5. Put the human gate at the message going out and the money going out, nowhere else. Tell me which
   steps run unattended and which need my hand.

CONSTRAINTS: a pilot is not revenue; no pilot without a success metric and a path to paid; never
automate the trust decision or spam. OUTPUT: a sales-motion map, a filled pilot-design template,
and the pilot-to-paid gate, then ONE next action.