War-game a pricing add-on before SKU mapping, entitlement rules, and sales talk tracks harden into how every quote gets built.
Pricing add-ons fail when the SKU name invents value the product does not deliver, when entitlements disagree between billing and the product UI, when sales discounts the add-on into free forever, and when finance cannot show attach rate without dual-counting seats. A neat pricing table is not evidence.
What must be frozen
State the add-on name and price, which plans can buy it, what unlocks when it is purchased, who owns discount exceptions, and the success metric for attach after two quarters. Attach the entitlement matrix, billing plan map, sales one-pager, and the kill criteria if support tickets or refunds spike. If product, finance, and sales disagree on whether the add-on is optional or effectively required, reconcile before seating.
Name the decision you will make if the war game finds nothing new, and the hold criteria if any entitlement still lacks a measured unlock path or a named discount owner.
Where it breaks
- Value fiction: copy that promises outcomes the feature set cannot show in a demo.
- Entitlement blur: billing unlocks that never appear in the product within the promised lag.
- Discount theater: exceptions that become the default without a published floor.
- Attach math: success metrics that dual-count seats, trials, or bundled giveaways.
- Support load: "what did I buy" tickets your macros cannot clear from the same SKU sheet.
Optional counsel seat if consumer or regulated pricing rules bind the form. Optional customer success seat if the add-on changes renewal conversations.
Run it
Feed Pingpong the add-on brief, entitlement matrix, and open risk list. Early passes steelman the SKU. Later passes attack from buyer, sales, finance, support, and product seats. End with a pass that turns surviving objections into clearer entitlements, a published discount floor, or a hold. Delete invented "customers already ask for this" claims and dual-counted attach.
Ask sales and finance seats to price the behavior the new add-on will invite. If day-one copy promises a must-have while the product still ships the capability free for a quarter, buyers will wait you out. Write the intended attach path, the discount owners, and the language you will refuse, then attack whether margin still holds under that discipline.
Force a day-after narrative: what happens if a large account refuses the add-on and threatens churn, if a competitor undercuts the SKU, or if support cannot explain the unlock. If those stories are stronger than your mitigation plan, fix the package before you publish. Related: war-game a pricing change, war-game a packaging change, war-game a pricing floor, before you change pricing, and the war-game decisions hub. Process: how to run a Pingpong.