To war-game a pricing change before you announce it, put the new and old pricing structure, the revenue model with its churn and downgrade assumptions, the customer base broken out by segment and contract terms, the rollout and notice plan, and the sales and customer success plan into one request. Then instruct Pingpong to test the change from three sides: the revenue model, the customers who will pay more, and the teams who will explain it. Ask where the model overstates the gain, which customers face the largest increase, what contract terms limit the change, and what the board should watch after launch. Do it before the board approves a forecast that includes the new revenue.
This page is for chief executives, chief financial officers, and revenue leaders preparing a price increase or a new pricing model for existing customers. It covers the decision and the rollout. Executive starting points live under Pingpong for executives.
Five things to settle before the announcement
- Who is affected, and when. New customers only, existing customers at renewal, or everyone on a set date? Which contracts cap increases or require longer notice?
- The model by segment. An average increase hides the spread. Small customers often face the largest percentage change and churn the most.
- Downgrade paths. New tiers can let some customers pay less. The model should count them.
- Team readiness. Sales and customer success need scripts, clear discount authority, and compensation that rewards holding the new price.
- Signals and a review point. Which numbers will show trouble early, and when will the board look again?
A worked example
This example is illustrative and does not describe a customer. A 400-person workflow software company plans to move existing customers from per-seat pricing to usage tiers at renewal. The average increase is 18%. The board deck forecasts $9 million in added annual recurring revenue over the next year, assuming three points of additional churn.
The chief financial officer pastes the pricing proposal, the revenue model, the customer list with segment, contract end date, and price terms, the renewal calendar, the sales compensation plan, and the draft customer notice.
A useful pass starts with the model. It applies the full increase to every renewal in the next twelve months, but about 35% of recurring revenue sits on multi-year contracts that cap annual increases at 5%. Some heavy-seat, low-usage customers would move to a cheaper tier, and the model does not count that loss. Rebuilt with both, the added revenue falls to roughly $5 million.
Then the customers. The smallest 40% of accounts face an average increase of about 35%, while the largest accounts see about 8%. The smallest accounts already have the highest churn, so the flat three-point churn assumption is likely too low for them. Some contracts require 60 days of notice before a price change, and the draft notice plan allows 30.
Then the teams. Account executives are paid on new bookings, not renewal increases, so they have little reason to hold the new price. Customer success managers have no guidance on discounts and would likely negotiate one renewal at a time. Nothing in the plan tells the board what early signal would prompt a change of course.
The chief financial officer and chief revenue officer revise the plan. The forecast shows a base case near $5 million with a range on each side, built by segment and contract term. First-year increases for the smallest accounts are capped at 15%. Notice periods follow each contract. A discount authority table sets who can approve what. Renewal compensation includes a component for holding price. The board will see weekly churn, downgrade, and discount figures and review results after the first two monthly renewal groups.
A request you can copy
Below are our current and proposed pricing, our revenue model and its assumptions, our customer base by segment and contract terms, our renewal calendar, our rollout and notice plan, and our sales compensation and customer success plans. Test the change from three sides: the revenue model, the customers paying more, and the teams explaining it. Flag contract caps and notice terms the plan ignores, downgrade paths the model leaves out, and segments where churn is likely to exceed the assumption. Rebuild the revenue estimate by segment and list what the board should monitor after launch.
For the same change seen from one large account's side, see role-play the enterprise buyer before procurement. To check how the new revenue affects the cash plan, see war-game a cash runway brief before the number reaches the board.
How Pingpong runs the war-game
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. Recheck every figure in your own model and confirm contract terms with counsel. For the steps inside the app, see running your first review.
What a model can't war-game
A model does not know how your customers value the product, how competitors will respond, or what your sales team hears on calls. Customer conversations and early results will tell you whether the price holds.
When the plan goes to the board, see war-game a decision before the board meeting. More guides live under work decisions before you commit.