To rehearse an enterprise deal before it reaches procurement, put the proposal, the order form, the master services agreement, your security questionnaire answers, and the concessions you are authorized to give into one request. Then instruct Pingpong to play the buying committee: procurement, security, legal, and the executive sponsor who has to defend the purchase internally. Ask each seat to name the first thing it would push back on, quote the clause or answer behind that pushback, and say what would let the deal move forward. Run it before the first procurement call.
This page is for chief executives and revenue leaders preparing a large B2B deal, especially one whose terms the board or a deal committee has already bounded. For a rival reading your pricing or launch plan, see role-play the competitor reading your plan. Executive starting points live under Pingpong for executives.
What the enterprise buyer seat is for
An enterprise purchase above a few hundred thousand dollars a year rarely has one buyer. Procurement reads the price and payment terms and asks for a benchmark. Security reads the questionnaire, the audit report, and the subprocessor list. Legal reads the agreement, usually starting with the liability cap, indemnities, and termination rights. The sponsor needs a business case in the format their finance team uses. Each seat can stall the deal on its own, and they often raise objections in sequence, so a concession you give procurement in week two can reopen a term legal settled in week one.
The role-play is most useful when you tell it where your authority ends. If the board approved a pricing floor or a liability cap, the model can flag which buyer requests would cross that line, so you can get approval before the negotiation starts.
A worked example
This example is illustrative and does not describe a customer. A 120-person workforce scheduling software company is about to send a proposal to a retailer with 900 stores in the United States and Canada. The deal is $1.4 million over three years for 2,400 store managers, with an 18 percent multi-year discount and a 90-day rollout. Earlier in the quarter, the board set two limits for deals of this size: annual fees no lower than $380,000, and a liability cap of twelve months of fees.
The chief executive pastes the full package and both board limits, and asks Pingpong to answer as the retailer's buying committee, seat by seat.
A useful pass starts with procurement. It would ask for termination for convenience after year one, which turns the three-year discount into a one-year price, and for payment at net 90 against the vendor's net 30. Security would note that the audit report covers the core platform but excludes the mobile app the store managers would use every day, and that one analytics subprocessor stores data only in the United States, which matters for the Canadian stores. Legal would ask for uncapped liability for data breaches, beyond the board's twelve-month cap. The sponsor, the head of store operations, would need payback shown per store, because that is how the retailer's finance team approves operating spend.
The chief executive makes four changes before the proposal goes out. Termination for convenience is offered after year one only with a price step back to the single-year rate. Payment terms move to net 60, written down as the walk-away point. The security package adds a letter with the date the mobile app joins the next audit, plus a Canadian hosting option for the analytics data. The chief executive also asks the board's deal committee to approve a data breach super-cap of two times annual fees now, so the answer is ready when legal asks.
A request you can copy
Below are my proposal, order form, standard agreement, security questionnaire answers, and the limits I am authorized to negotiate within. Role-play as the buyer's committee: procurement, security, legal, and the executive sponsor. For each seat, open with the first objection you would raise, quote the clause, price line, or answer behind it, and say what would satisfy you. Flag any request your seat would make that falls outside my stated limits. Note where a concession to one seat would reopen something another seat had accepted. Stay in the buyer seats for the whole reply.
Paste the buyer's own procurement policy or security requirements if they sent them,.
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 clause against the actual documents 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 buyer's internal approval thresholds, which incumbent vendor procurement is quietly benchmarking against, or how much leverage the sponsor has with their own chief financial officer. Contract language and security commitments should be reviewed by your counsel and security lead before they go to the buyer.
When the deal itself needs board approval, see war-game a decision before the board meeting. For a finished package headed to a signature, see review a high-stakes decision package. More guides live under work decisions before you commit.