When an AI service deal stalls: separate users from who pays
When a deal stalls, before another demo, split what you heard from what is unconfirmed for the user, payer and approver.
Key points
- Separate pay & rollout from user praise
- AI-found job titles stay unconfirmed
- Turn gaps into questions before the call
- Pick a next move: meet, brief, or wait
Contents
Separate pay & rollout decisions from the contact's praise
A&A perspective
A contact who tried your service and liked it is one fact, and a decision to pay for it and roll it out is another, so write them on separate rows of a table you keep for each deal. The three roles here are the person who will use the service, the person who decides to pay, and the person who checks whether it can be brought in. A later section shows the table with an example.
A&A perspective
The setting is a company that sells a service from its own industry to other businesses and has built AI into the way it delivers that service. A contact at a client company liked the trial and asks for another demo and a little more material. Still, nobody mentions placing an order.
A&A perspective
The user is the person who receives what the service produces in daily work and can push back on its quality. The payer is the person who signs off on the amount, or who decides whether to take it to the person who signs. The approver is the person who checks whether it fits the company's rules, including how information is handled.
From the sources
Y Combinator (YC), an organization that funds early-stage startups, published a post in October 2018 in which a YC partner answered founders' questions. The first recommendation for companies starting to sell was to figure out who the actual buyer of the product is. The post describes that buyer as the decision-maker who pulls out the credit card or signs the bill.
From the sources
The same post advises picking first customers that do not have a procurement team yet: companies where the person who likes and uses the product can decide to pay for it themselves.
A&A perspective
Automate & Augment (A&A), the company writing this article, reads this advice as resting on the view that the user and the decider can be different people. In services sold to businesses, it is common for the person who is happy with the output and the person who signs off on the cost to be different. A contact's "this looks good" confirms nothing about payment or rollout.
A&A perspective
The positive signal is real, so the owner tends to spend spare hours on extra demos and material. The work moves, yet the deal is no further along than it was a week ago. Writing the contact's satisfaction and the authority to pay in separate cells keeps the two from being mistaken for each other.
A&A perspective
If the user and the payer are the same person and the amount is within what that person can approve alone, there is no need to split the rows. The companies YC recommends as first customers are the ones that meet this condition.
AI-found job titles stay unconfirmed
A&A perspective
Having AI research a prospect tells you job titles and industry, but not whether that person can decide to pay, so the title goes in the Unconfirmed column.
From the sources
Clay, a tool that researches companies automatically, describes on its own website how it is used by Lovable, an AI service that builds apps from requests written in plain language. When a company submits Lovable's enterprise form, Clay researches that company in real time.
From the sources
It looks up the industry, the person's role, whether there is an existing relationship, and what the company's current priorities are likely to be. Based on that, the prospect is matched to the sales rep best placed to help. The page says reps receive a brief for every meeting covering who the company is and what problems it is likely solving.
From the sources
The page says nothing, however, about any step that checks purchasing authority, budget or internal sign-off. It shows no date, and it is a customer story written by Clay itself.
A&A perspective
Reading the YC post and the Clay page side by side, A&A sees it this way. AI research is strong on what can be seen from outside, such as industry and job title. It is weak on conditions inside the client company: who actually decides to pay, whether there is budget for it this term, and which department has to check before rollout.
A&A perspective
Research before a sales meeting is one of the tasks that is easy to hand to AI. But if a title found by research is treated as confirmed authority, the Unconfirmed column looks filled when it is not. A title is a clue, not proof that the person can sign. An org chart on the client's website and the contact's guesses go in the Unconfirmed column too.
| What to confirm | What AI company research shows | Unconfirmed until you ask |
|---|---|---|
| Who decides to pay | The person's job title (a clue) | Whether that person can sign off |
| This term's budget | What the company's priorities are likely to be | Whether there is budget for it this term |
| Checks before rollout | Industry, and any existing relationship | Which department has to check |
Turn gaps into questions before the next meeting
A&A perspective
Write each gap in the Unconfirmed column not as a note such as "budget unconfirmed" but as a question you can ask as is at the next meeting.
A&A perspective
Keep one table per deal.
A&A perspective
The rows are the user, the payer and the approver.
A&A perspective
The columns are what you heard from the person, what is still unconfirmed, and whom to ask next.
A&A perspective
Two rules apply. First, put under heard only what the person told you directly or what you learned from something they wrote. Second, write every unconfirmed item as a question.
Hypothetical example
Here is a made-up example. Take a service that sends companies a monthly report on what their competitors are doing. AI drafts the report and a staff member finishes it. A planning contact at a client liked the trial and asked for another demo.
Hypothetical example
The user row records what you heard: they will use it for the monthly competitor comparison, which now takes two days by hand. The unconfirmed item reads: "Can this output go into your regular internal meeting materials as it is?"
Hypothetical example
The payer row has nothing under heard. Its unconfirmed item reads: "Who decides on this cost? If you decide within the year, what do you need, and by when?"
Hypothetical example
The approver row is empty under heard as well. Its unconfirmed item reads: "Does passing us the names of the competitors the report covers need an internal check?" For all three rows, the person to ask next is the planning contact.
Hypothetical example
Once the table is filled in, only the user row has anything heard. The other two rows are still empty under heard. Building another demo at this point would only satisfy, once again, the one person who is already satisfied.
A&A perspective
Now that the gaps are questions, what you prepare next is not material. It is a way to get those questions to the people who can answer them.
Pick a next move: joint meeting, decision brief, or wait
A&A perspective
Once the table is done, pick one next move out of three: meet in a joint meeting, brief with decision material, or wait for the client's internal check.
A&A perspective
A joint meeting means asking the contact to bring in the payer or the approver. Choose it when the payer or approver row is empty and the contact can reach that person. What you write is not material but a short request the contact can easily pass on inside the company.
A&A perspective
Preparing decision material fits when the "ask next" column names the person you will meet and you know what that person wants to see. Make only what answers the questions in the Unconfirmed column, such as a cost breakdown or a comparison with the current manual work. An extra demo fits only when you learn that the user is not yet convinced by the output.
A&A perspective
How to build a demo that checks whether the user is convinced by the output is covered in another article, "Put the buyer's task in your AI demo: build a comparable eval set".
A&A perspective
Waiting fits when a check is under way inside the client and nothing you do will move it. Make nothing; just agree with the contact on what will be known by when.
Hypothetical example
In the made-up example, the payer and approver rows were empty. That calls for a joint meeting. The request you hand the contact could be as short as this.
Hypothetical example
"It looks like the monthly competitor comparison could go from two days to half a day. Could the person who decides on the cost and the person who checks information handling join us once for 30 minutes? We will only cover the cost breakdown and which information goes where."
A&A perspective
A joint meeting needs the contact's agreement first. Going over the contact's head to fill the empty cells can hurt their standing and lose you the deal. The table shows whom you need to meet, not whom you may contact.
Summary
A&A perspective
Write the contact's satisfaction and the pay and rollout decisions on separate rows of the table.
A&A perspective
A job title found by AI research does not confirm authority, so it goes in the Unconfirmed column.
A&A perspective
Before the next meeting, turn each unconfirmed item into a question you can ask as is.
A&A perspective
Look at whom each question is for, and pick one next move: a joint meeting, decision material, or waiting.
A contact's satisfaction is not proof that payment or rollout has been decided. Before building another demo, split what you heard from what is unconfirmed for each of the three roles, and let whom the open questions are for decide between a joint meeting, decision material, and waiting.
FAQ
What if the contact says, "I'll raise it with my boss myself"?
Don't push for a joint meeting; choose to wait. Leave it to the contact to raise it with their boss, make nothing yourself, and just agree, there and then, on when you will hear back.
Do I still need the table when I sell directly to an owner?
In most cases, no. If the user and the payer are the same person and the amount is within what they can approve alone, splitting into three rows takes more effort than it saves. If only the approval check remains, writing that one row is enough.
What if the empty cells never fill?
Treat that as an answer in itself. If the contact still cannot name the decider or the timing, lower the deal's priority and spend the freed time on other deals.
Sources & editorial note
Primary pages read for this article. Publication dates below belong to the sources; access dates record our research.
- Growth AMA with YC Partner Gustaf Alströmer
Y Combinator · 2018-10-29
Accessed 2026-10-24 - How Lovable uses Clay to scale one of the fastest-growing startups in history
Clay · undated customer story page
Accessed 2026-10-24