Pricing and packaging skill

Pricing and packaging — The headcount org chart — 16 departments, 172 skills, searchable (from the cbrock84/headcount README)

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Sets price, structures packages and tiers, and designs the monetization surfaces that carry them — upgrade paths, paywalls, and offer construction.

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Pricing and packaging

The highest-leverage number in the business and the least examined. Most companies are underpriced and have never tested it.

The pricing metric

Choose what you charge per before choosing how much. It should scale with the value the customer receives, be predictable enough to budget, and be something they cannot easily game.

Get this wrong and no amount of tuning the number fixes it — a metric that scales with your cost rather than their value creates a permanent argument at every renewal.

Setting the level

Anchor on value delivered, not cost incurred. Cost sets a floor and nothing else.

Evidence to gather: what the alternative costs them today including labor, what similar categories charge, and what current customers say about price — with the caveat that nobody says a price is too low. Willingness-to-pay research is directional, not decisive; people misreport.

If nobody ever objects to your price, it is too low. Some loss on price is correct.

Packaging

Tiers should map to distinguishable segments with different needs, not to arbitrary feature counts. Three is usually right; more creates paralysis and support load.

Each tier needs one obvious reason to upgrade, tied to something that grows with the customer's success. Gating on a feature they will never need does not drive upgrades; gating on a limit they will hit does.

Name tiers for who they are for, not by metal. "Team" and "Business" tell a buyer where they belong.

Monetization surfaces

Upgrade prompts and paywalls should appear at the moment of blocked value — when someone is trying to do the thing the tier does not allow, not on a schedule.

Explain what is behind the gate and why the limit exists. An unexplained wall reads as extraction. Show the value already received before asking for payment, and make declining easy — dark patterns buy one conversion and lose the account.

Changing price

  • Grandfather existing customers, or expect churn well beyond the price-sensitive segment.
  • Announce with real notice and a clear reason.
  • Change one thing at a time — price and packaging together makes the result unreadable.
  • Model the downside first: at what churn rate does this increase lose money?

Sources

references/sources.md in this skill lists the outside authorities that settle the questions here — what each one is authoritative for, and what you may do with it. Check them before answering on anything they cover, and cite what you used. Most are free to read and not free to reproduce; the use note on each is binding.

Never

  • Change price without telling existing customers before it takes effect and honoring what they already signed.
  • Pick a pricing metric the customer cannot predict. If they cannot forecast the bill, they will not sign.
  • Add a tier to close a single deal. Tiers are a permanent tax on every conversation after it.
  • Discount without taking something back in exchange — term, scope, payment timing, a reference. A free discount resets the price for everyone.
1---
2name: pricing-and-packaging
3description: Sets price, structures packages and tiers, and designs the monetization surfaces that carry them — upgrade paths, paywalls, and offer construction. Use this to set or change pricing, design or restructure tiers, choose a pricing metric, build an offer, design upgrade prompts and paywalls, or evaluate whether a pricing change is safe to make.
4---
5 
6# Pricing and packaging
7 
8The highest-leverage number in the business and the least examined. Most companies are underpriced
9and have never tested it.
10 
11## The pricing metric
12 
13Choose what you charge *per* before choosing how much. It should scale with the value the customer
14receives, be predictable enough to budget, and be something they cannot easily game.
15 
16Get this wrong and no amount of tuning the number fixes it — a metric that scales with your cost
17rather than their value creates a permanent argument at every renewal.
18 
19## Setting the level
20 
21Anchor on value delivered, not cost incurred. Cost sets a floor and nothing else.
22 
23Evidence to gather: what the alternative costs them today including labor, what similar categories
24charge, and what current customers say about price — with the caveat that nobody says a price is too
25low. Willingness-to-pay research is directional, not decisive; people misreport.
26 
27If nobody ever objects to your price, it is too low. Some loss on price is correct.
28 
29## Packaging
30 
31Tiers should map to distinguishable segments with different needs, not to arbitrary feature counts.
32Three is usually right; more creates paralysis and support load.
33 
34Each tier needs one obvious reason to upgrade, tied to something that grows with the customer's
35success. Gating on a feature they will never need does not drive upgrades; gating on a limit they
36will hit does.
37 
38Name tiers for who they are for, not by metal. "Team" and "Business" tell a buyer where they belong.
39 
40## Monetization surfaces
41 
42Upgrade prompts and paywalls should appear at the moment of blocked value — when someone is trying
43to do the thing the tier does not allow, not on a schedule.
44 
45Explain what is behind the gate and why the limit exists. An unexplained wall reads as extraction.
46Show the value already received before asking for payment, and make declining easy — dark patterns
47buy one conversion and lose the account.
48 
49## Changing price
50 
51- Grandfather existing customers, or expect churn well beyond the price-sensitive segment.
52- Announce with real notice and a clear reason.
53- Change one thing at a time — price and packaging together makes the result unreadable.
54- Model the downside first: at what churn rate does this increase lose money?
55 
56## Sources
57 
58`references/sources.md` in this skill lists the outside authorities that settle the questions
59here — what each one is authoritative for, and what you may do with it. Check them before
60answering on anything they cover, and cite what you used. Most are free to read and not free
61to reproduce; the use note on each is binding.
62 
63## Never
64 
65- Change price without telling existing customers before it takes effect and honoring what they already signed.
66- Pick a pricing metric the customer cannot predict. If they cannot forecast the bill, they will not sign.
67- Add a tier to close a single deal. Tiers are a permanent tax on every conversation after it.
68- Discount without taking something back in exchange — term, scope, payment timing, a reference. A free discount resets the price for everyone.
69 

Discussion

Alternatives

Mobile App Monetization StrategyWhen the user wants to design or optimize their app's monetization — pricing, paywalls, subscriptions, or in-app purchases. Also use when the user mentions "pricing", "paywall", "subscription", "IAP", "how to monetize", "revenue optimization", "free trial", or "conversion to paid". For retention impact, see retention-optimization. For competitive pricing, see competitor-analysis.Sales & ecommerce · MITPaywall Optimization (Subscription Apps)When the user wants to design, test, or optimize their app's paywall — layout, copy, pricing display, trial offers, plan structure, hard vs soft paywall, paywall placement, or paywall A/B tests. Use when the user mentions "paywall", "paywall design", "paywall conversion", "trial-to-paid", "soft paywall", "hard paywall", "paywall A/B test", "paywall copy", "plan picker", "annual vs monthly display", "best paywall", "RevenueCat paywall", "Superwall", "Adapty", or "my paywall isn't converting". For overall pricing strategy and monetization model choice, see monetization-strategy. For trial nurture, dunning, and churn, see subscription-lifecycle. For where in the onboarding the paywall fires, see onboarding-optimization.Sales & ecommerce · MITPricing Strategy (Lenny's Podcast)Help users validate willingness-to-pay, select the right value metrics, and continuously optimize pricing and packaging to drive growth.Sales & ecommerce · MIT$100M Money ModelsDesigns a deliberate sequence of offers (attraction, upsell, downsell, continuity) so a new customer generates enough cash within ~30 days to fund acquiring the next one - Alex Hormozi's client-financed acquisition. Use when customers buy once and never again, when CAC eats all the profit, when you can't afford to advertise profitably, when the business grows but cash shrinks, when you sell one product at one price, when deciding what to sell first or next, or when structuring upsells, downsells, payment plans, trials, and continuity. Covers the 30-day payback rule, attraction/upsell/downsell/continuity offer types, and cash-flow sequencing for validated markets.Sales & ecommerce · MIT