To rehearse a mid-market sale before you send the proposal, give Pingpong the proposal, the order form, your pricing, and a few lines on the buyer: who signs, who will use the product every day, how the company pays its bills, and its busiest months. Then instruct Pingpong to read the proposal as that owner or operations lead. Ask for the first line that would make them hesitate, the term they would push back on, and the question they would ask on the next call. Run it before the proposal goes out.
This page is for founders and chief executives selling to companies of roughly 50 to 500 people, where one or two people decide. If the buyer has a procurement team, a security review, and in-house counsel, see role-play the enterprise buyer before procurement. Executive starting points live under Pingpong for executives.
How a founder-led buyer decides
In a company this size, the person who signs often also uses the product, or sits next to the person who does. They are spending money they can see on their own profit and loss statement. They usually compare your proposal with the spreadsheet and phone calls they use today, and they ask what happens if the rollout goes badly in their busy season.
These buyers read the whole proposal, including the contract terms an enterprise buyer would hand to counsel. An automatic renewal with a 90-day notice window, an onboarding fee with no listed deliverables, or a security appendix written for a bank tells them the vendor sells to someone else. They also want to know who they will call when something breaks.
What to tell the model about the buyer
- Who signs and who uses the product daily.
- How the company is paid and when cash is tight.
- The months when a rollout would hurt.
- What they use now and what it costs them.
A worked example
This example is illustrative and does not describe a customer. A 30-person software company sells a quoting and estimating tool. The board approved a push into mid-size contractors this year, and the first serious deal is a family-owned commercial roofing company with 140 employees. The second-generation owner signs. The chief estimator, who has built every bid in a spreadsheet for eleven years, will use the tool daily.
The draft proposal is the company's enterprise template: $38,000 a year paid upfront, a $16,000 onboarding fee, a three-year term with automatic renewal and 90 days' notice, a twelve-page services agreement, a security appendix, and go-live in April. References are two national construction firms.
The chief executive asks Pingpong to read the proposal twice in one reply, as the owner and as the chief estimator.
A useful pass starts with the owner. Paying $54,000 upfront in January lands in the slowest cash months of a roofing year. The renewal clause reads as a trap to someone who has been caught by one before. An April go-live collides with the start of roofing season, when bids are due daily. From the estimator's seat, nothing in the proposal says whether a bid gets out faster, and the onboarding fee does not say who moves eleven years of templates. Neither reader would recognize their company in the references.
The chief executive cuts the proposal to six pages. Billing moves to quarterly. The onboarding fee is split across three milestones: templates imported, the first 20 bids sent from the tool, and estimator training. Go-live moves to February. The term becomes one year with 30 days' notice, and two references come from contractors under 200 people. The proposal names the support lead the estimator will call. Before sending, the chief executive writes down a price floor, so a request for a discount on the next call has an answer.
A request you can copy
Below are my proposal, order form, and pricing, plus notes on the buyer: who signs, who will use the product, how the company manages cash, and its busy season. Read the proposal as the person who signs. Tell me the first line that would make you hesitate, the term you would push back on, and the question you would ask on our next call. Then read it again as the daily user and tell me what they would need to see to support the purchase. Point out anything that suggests we built this proposal for a much larger customer. Stay in the buyer's seat.
Paste discovery call notes, especially anything the buyer said about past vendors.
How Pingpong runs the role-play
The web review app sends your request through several models in order. Each later model receives the original request and every earlier answer, with instructions to assess the work so far. Check every flagged point against your call notes before you change the proposal. For the steps inside the app, see running your first review.
What a model can't role-play
A model does not know this owner's history with vendors, how the estimator feels about being replaced by software, or what a competitor quoted them last week. Changes to contract terms should go past your counsel before you send them.
When the deal opens a segment the board is watching, see war-game a decision before the board meeting. More guides live under work decisions before you commit.