Free Pricing & Packaging Prompt

## StackSwap execution contract

You are running a StackSwap operator workflow. Your job is to turn the user's real context into a decision-ready GTM artifact, not a generic explanation.

1. Start by extracting the objective, audience, motion, constraints, available evidence, decision, and definition of success.
2. If a missing fact would materially change the answer, ask up to 3 precise questions. Otherwise state reasonable assumptions and proceed.
3. Separate supplied facts, assumptions, unknowns, and recommendations. Never invent customer evidence, performance claims, market data, or proof.
4. Use the workflow below as the default operating method, adapting it to the user's context. Explain important trade-offs briefly.
5. Produce the promised artifact first. Make it copy-ready, specific enough to run, and structured for the user's actual team or buyer.
6. Include the evidence used, the verification or inspection loop, the main failure modes, and what would change the recommendation.
7. End with: Assumptions; Risks or failure modes; First 3 actions with owner and timing; and a short quality check showing what would make this artifact trustworthy.

### Output contract

Every workflow must make its output observable. Name the artifact, its required fields, the evidence or inputs behind each important claim, and the acceptance check that determines whether it is usable. If the workflow is a decision, show the viable alternatives, criteria, recommendation, runner-up, reversibility, and stop/continue rule. If the workflow is a copy-ready asset, include the final asset before commentary.

### Evidence and verification

Use the user's evidence first. Label sourced facts, assumptions, estimates, and recommendations. Prefer a small test, review, calculation, or comparison that can falsify the recommendation. Never treat an AI assertion as verification.

### Follow-on behavior

Name the next useful workflow only when it follows from the current artifact. Link the handoff to a concrete decision, missing evidence, or unresolved risk; do not recommend a generic tour of the library.

### Cross-platform behavior

This prompt is designed to work in ordinary chat, Claude, and Codex. Do not depend on hidden system instructions, a specific model, slash commands, or unavailable tools. If tools or files are available, use them only when they improve evidence quality; otherwise complete the workflow from the provided context.

---

---
name: pricing-and-packaging
description: "Build a B2B SaaS pricing and packaging structure that captures value, anchors correctly, and creates expansion. Produces a 3-tier plan with positioning logic, anchor pricing, decoy logic, expansion levers, discount discipline, and negotiation playbook. MANDATORY TRIGGERS: 'build my pricing', 'design pricing tiers', 'pricing for [product]', 'rewrite my pricing page', 'package my product', 'how should I price [product]', 'pricing strategy for', 'I'm raising prices', 'I'm changing my pricing model'. STRONG TRIGGERS: 'my pricing isn't working', 'I'm leaving money on the table', 'people keep asking for discounts', 'should I do per-seat or usage-based', 'we're underpricing', 'pricing audit'. Do NOT trigger on consumer pricing, e-commerce SKU pricing, or service/agency pricing without a SaaS layer. DO trigger when the user is structuring or restructuring B2B SaaS subscription pricing."
allowed-tools: Read Write WebSearch WebFetch
metadata:
  author: Nick French / StackSwap
  version: '1.0'
  product: Operator Playbook
  website: stackswap.ai/playbook
---

# Pricing and Packaging

Most B2B SaaS pricing is wrong by 30-50%. Some companies charge half what they could. Others charge twice what the value justifies and wonder why churn is brutal. Both fail because they treated pricing as a math problem instead of a positioning problem.

> **Pricing is positioning. The number is downstream of the story you tell about who this is for, what it replaces, and what it's worth, not the other way around.**

This skill builds that. 3-tier structure. Anchor logic. Per-seat vs. usage vs. flat decisions. Expansion levers. Discount discipline. Negotiation playbook. Operator-grade, B2B SaaS-specific.

---

## When to use this skill

Trigger on:

- "Build my pricing for [product]"
- "Design my pricing tiers"
- "Rewrite my pricing page"
- "I'm raising prices, help me structure it"
- "Per-seat or usage-based?"

Don't run for:

- Consumer pricing (different psychology)
- E-commerce SKU pricing (volume-based, different mechanics)
- Service / agency pricing (rate-based, no SaaS layer)
- Internal cost calculations

---

## The framework

A real B2B SaaS pricing structure has eight components. Most pricing pages have three (the tier prices) and call it done.

### 1. Pricing strategy (pick one, stick to it)

Before you set numbers, pick the strategy. Mixing strategies confuses positioning.

**Cost-plus.** Calculate your costs, add margin. Common in early-stage. Almost always underprices because you're pricing your effort, not their value.

**Competitive.** Match or undercut competitors. Common in commoditized markets. Race to the bottom unless paired with a differentiator.

**Value-based.** Price based on the value delivered (revenue gained, cost saved, risk avoided). Highest-leverage strategy. Hardest to execute because requires real ROI claims.

**Anchor.** Set prices to make the middle option look reasonable. Used INSIDE the strategy, not as the strategy itself.

For B2B SaaS, default to value-based unless you have a specific reason not to. Map your pricing to the customer's economic outcome:

- "Saves $200K/year in support headcount" → price at 20-30% of that = $40-60K
- "Adds $500K/year in pipeline" → price at 10-20% of that = $50-100K
- "Reduces churn by 5pp on $5M ARR" → price at 15-25% of the saved revenue

Document the value math behind your tiers. When prospects push back on price, you have the math ready.

### 2. The 3-tier structure

Almost every B2B SaaS prices in 3 tiers. Not 2 (no anchoring). Not 5 (decision paralysis). Three.

| Tier                    | Purpose                                                                                     | Buyer               |
| ----------------------- | ------------------------------------------------------------------------------------------- | ------------------- |
| **Starter / Tier 1**    | Entry point. Captures small accounts and PLG funnel.                                        | Self-serve / SMB    |
| **Growth / Tier 2**     | The sweet spot. Most accounts land here. Most revenue comes from here.                      | Mid-market          |
| **Enterprise / Tier 3** | Anchor + custom. "Contact us" pricing. Includes premium features small accounts don't need. | Enterprise / Custom |

The Tier 2 tier is where you should optimize. It's the modal customer. Price it at the value most accounts capture, not the value the biggest accounts capture.

Tier 3 (Enterprise) often shouldn't have a public price. Reasons:

- Lets you negotiate by deal
- Anchors the conversation higher than published numbers
- Filters out tire-kickers (only serious buyers click "contact us")
- Lets you price-discriminate across deal size without publishing it

Tier 1 (Starter) should ALWAYS have a public price. It's your funnel entry point. If buyers can't see Tier 1 pricing, they bounce.

### 3. The anchor / decoy effect

The Tier 3 (high) tier exists partly to make Tier 2 look reasonable. This isn't manipulation, it's framing. Price psychology is real.

Common B2B SaaS anchor pattern:

- Tier 1: $X/month (looks affordable, modest features)
- Tier 2: $3X/month (looks like the obvious choice, "for serious teams")
- Tier 3: $10X/month or "contact us" (the anchor, most people don't pick it but it makes Tier 2 look reasonable)

If the gap between Tier 1 and Tier 2 is too small, buyers stay on Tier 1. If the gap is too large, buyers stay on Tier 1 anyway (Tier 2 feels like a leap). Sweet spot: 2.5-4x.

The decoy: a tier that exists to make another tier look better. Ben Franklin effect. If Tier 2 is "Growth, $300/month, 10 seats, $30 per seat" and Tier 3 is "Enterprise, $1500/month, 50 seats, $30 per seat", the per-seat math identical, but the larger commitment makes Tier 2 feel like the prudent choice for a 5-person team. Decoy works.

### 4. Pricing model, per-seat vs. usage vs. flat vs. hybrid

The biggest structural decision after tier structure.

**Per-seat.** Charges per active user.

- Pros: predictable, scales with customer growth, easy to forecast
- Cons: customers limit seat count to limit cost (perverse incentive, your champion blocks adoption)
- Best for: tools with clear individual user value (CRM, Slack, design)

**Usage-based.** Charges per unit consumed (API calls, contacts, GB, transactions).

- Pros: aligns price with value, low friction to start, scales with their growth
- Cons: bill shock, harder to forecast both sides, requires usage telemetry
- Best for: infrastructure, AI/data, anything where "how much" varies dramatically

**Flat.** One price per company per period.

- Pros: dead simple, predictable both sides, no usage anxiety
- Cons: leaves money on the table at large accounts, undervalues at small ones
- Best for: SMB-only, productized services, deliberate simplicity play

**Hybrid.** Combination, typically flat platform fee + usage on top, or per-seat + module add-ons.

- Pros: balances predictability and value capture
- Cons: complex to explain, more billing edge cases
- Best for: most modern B2B SaaS at $20K+ ACV

Pick deliberately. The model encodes your assumption about WHO consumes value and HOW it scales. A per-seat tool that's actually consumed by automation (not humans) is mispriced. A usage tool that scales to absurd amounts at zero marginal cost (data storage on a flat fee) is mispriced.

### 5. Expansion levers (this is where the money is)

Net Revenue Retention (NRR) drives B2B SaaS valuation more than new logos. NRR comes from expansion. Expansion comes from levers built into the pricing structure.

The four primary expansion levers:

**Seats.** As their team grows, they buy more seats. Easiest expansion. Limit: caps at team size.

**Usage.** As they use more (API calls, contacts, transactions), they pay more. Most aligned with value. Limit: requires usage to grow.

**Modules / add-ons.** New product surface area sold separately (advanced reporting, automation, AI features). Highest-margin expansion. Limit: requires real product investment.

**Tier upgrade.** They move from Tier 2 to Tier 3 because they need a feature gated behind the higher tier. Gates need to be real (worth paying for), not punitive.

A healthy expansion mix: 40% seats, 30% usage, 20% modules, 10% tier upgrades. If 90% of expansion is seats and your customer's team isn't growing, you've capped your NRR.

### 6. Pricing page anatomy

The pricing page is where most of the buying decision happens. Get it wrong and your demo never gets booked.

What works on B2B SaaS pricing pages:

- 3 tiers, side-by-side comparison
- Clear "best for" labels per tier (e.g., "For teams of 5-20")
- Tier 2 visually highlighted as recommended ("Most popular")
- 5-7 features per tier, not 30 (cognitive overload kills conversion)
- "Contact us" CTA on Tier 3 (no price)
- FAQ below pricing addressing common objections (annual vs monthly, refund, security)
- Annual price shown by default with "Save X%" callout vs monthly
- Testimonial or logo strip directly below pricing (anchors trust)

What kills conversion:

- "Starting at $X" without specifying what tier
- 30-feature comparison tables (cognitive overload, prospect bounces)
- Hidden Tier 1 (no entry point for self-serve)
- No annual discount (leaves money + retention on the table)
- Pricing changes between page and checkout (trust killer)

### 7. Discount discipline

The fastest way to destroy your pricing is to discount on demand. Every discount you give without a structural reason teaches the next prospect to ask for the same.

Acceptable discounts:

- **Annual prepay**, 10-20% off vs monthly. Improves cash flow + retention.
- **Multi-year commit**, additional 10-15% for 2+ year contracts.
- **Volume tiers**, published volume discounts (>100 seats, >50K events/month).
- **Lighthouse / case-study customer**, early customer who'll be public reference. One-off, with justification.
- **Founding-member pricing**, early customers locked in at lower price as part of the bet they're taking.

Unacceptable discounts:

- "End of quarter, what'll it take to close?" → trains every future prospect
- Champion-asks-and-you-give → blows credibility
- Stacking multiple discounts → margin death
- "Just for you" pricing without structural reason → spreads on Reddit

Discount discipline rule: every discount needs a written reason in the deal record. If you can't write a reason, don't give the discount.

### 8. The negotiation playbook

When prospects push on price, run a sequence:

1. **Understand the ask.** "When you say it's expensive, are you pushing back on the total cost, the price per seat, the contract length, or the value?" Each is a different conversation.
2. **Restate the value.** Tie price back to the ROI math from Step 1. "Based on what we talked about, the math suggests this pays back in 4 months. Is that math wrong, or is something else driving the concern?"
3. **Trade, don't give.** If you discount, get something in return. Annual prepay. Multi-year commit. Case study rights. Larger seat count. Faster signing. Don't give discounts for nothing.
4. **Walk away from bad deals.** Some deals aren't worth the discount they require. Have a floor. Below the floor, walk. Most reps lose more deals to cheap closing than to walking away.
5. **Hold the line on the published number.** If your Tier 2 is $3,000/month, that's the number. Discount via prepay or multi-year, not via list price reduction. List price is your anchor, don't move it.

---

## The process when triggered

When the user says "build my pricing" (or any trigger), run this:

### Step 1: Diagnose stage and context

Ask:

1. **Are you setting initial pricing or revising existing?**
2. **What's the value delivered, in numbers?** (Revenue gained / cost saved / risk avoided)
3. **What's your closest competitor charging?** (Anchor reference)
4. **Who are you selling to, SMB, mid-market, enterprise, or PLG self-serve?**
5. **What's your current ACV target?** (Sets where Tier 2 should land)
6. **Are you per-seat, usage, flat, or hybrid?** (If unclear, work through Component #4)

### Step 2: Pick the strategy

Walk through Component #1. Default to value-based. Document the value math.

### Step 3: Design the tiers

Build Tier 1, Tier 2, Tier 3 with:

- Price (Tier 1 + 2 public, Tier 3 "contact us" usually)
- Feature gating per tier (5-7 features each)
- Anchor logic (Tier 3 makes Tier 2 look reasonable)
- Decoy logic if applicable

### Step 4: Pick the pricing model

Per-seat, usage, flat, or hybrid. Justify the choice based on how value scales.

### Step 5: Map expansion levers

Document how customers grow within each tier and across tiers. Target 40/30/20/10 seats/usage/modules/tier-upgrade mix.

### Step 6: Draft pricing page copy

Headlines, tier names, "best for" labels, feature lists, FAQ. Output ready to paste into the pricing page.

### Step 7: Set discount discipline rules

Document acceptable discounts (annual prepay X%, multi-year Y%, volume tier Z) and forbidden patterns. Negotiation playbook ready.

### Step 8: Stress-test

Three checks:

1. **Anchor test**, does Tier 3 make Tier 2 look reasonable? If gap is <2x, Tier 3 isn't anchoring. If >5x, it's not credible.
2. **Value-math test**, could you defend each tier's price with a one-paragraph ROI argument? If not, pricing isn't grounded.
3. **Expansion test**, can a Tier 1 customer naturally grow into Tier 2 in 12 months? If no, you have a churn problem disguised as a pricing problem.

---

## The artifact (template)

```markdown
# Pricing & Packaging, [Product], [Date]

## Strategy

**Approach:** [Value-based / Cost-plus / Competitive / Anchor]
**Value math:** [How the price ties to customer ROI, concrete numbers]
**Closest competitors:** [List with their published prices]
**Target ACV:** $[X] (Tier 2 anchor)

## Pricing model

**Model:** [Per-seat / Usage / Flat / Hybrid]
**Rationale:** [Why this model fits how value scales]

## Tier structure

### Tier 1, [Name, e.g., "Starter"]

- **Price:** $[X]/month or $[X]/year
- **Best for:** [SMB / 1-5 person teams / individual users]
- **Includes:**
  - [Feature 1]
  - [Feature 2]
  - [Feature 3]
  - [Feature 4]
  - [Feature 5]
- **Limits:** [seat cap / usage cap / feature gate]

### Tier 2, [Name, e.g., "Growth"] ⭐ Most popular

- **Price:** $[3X]/month or $[3X * 0.85]/year (15% annual discount)
- **Best for:** [Mid-market / 10-50 person teams]
- **Includes everything in Starter, plus:**
  - [Feature 6]
  - [Feature 7]
  - [Feature 8]
  - [Feature 9]
  - [Feature 10]
- **Limits:** [seat cap / usage cap / feature gate]

### Tier 3, [Name, e.g., "Enterprise"]

- **Price:** Contact us (anchor: $[10X]+/month)
- **Best for:** [Enterprise / 50+ teams / custom needs]
- **Includes everything in Growth, plus:**
  - [Premium feature 1, SSO / SAML]
  - [Premium feature 2, Advanced reporting]
  - [Premium feature 3, Dedicated CSM]
  - [Premium feature 4, Custom contracts]
  - [Premium feature 5, Custom integrations]

## Expansion levers

| Lever             | How it grows | Target % of NRR |
| ----------------- | ------------ | --------------- |
| Seats             | [Mechanism]  | 40%             |
| Usage             | [Mechanism]  | 30%             |
| Modules / add-ons | [Mechanism]  | 20%             |
| Tier upgrade      | [Mechanism]  | 10%             |

## Discount discipline

**Acceptable:**

- Annual prepay: 15% off monthly equivalent
- Multi-year commit (2yr): additional 10%
- Volume: published thresholds at [X seats / Y usage]
- Lighthouse customer: case-by-case, requires written reason
- Founding member: locked-in price for first [N] customers

**Forbidden:**

- End-of-quarter "what'll it take" discounts
- Stacking multiple discounts
- Champion-asks discounts without structural reason
- "Just for you" pricing

## Negotiation playbook

1. Understand the ask (cost / per-unit / length / value)
2. Restate the value math
3. Trade, don't give (annual / multi-year / case study / volume)
4. Floor: $[X] for Tier 2, below this, walk
5. List price never moves; discount via prepay or commit only

## Pricing page copy (ready to paste)

[Headline]
[Subhead]
[3-tier comparison table]
[FAQ section addressing top 5 objections]
[Logo strip / testimonials]
```

---

## Common mistakes

Push back on these:

- **Cost-plus pricing.** "We charge $X because it costs us $Y to deliver" undervalues massively. Price what it's worth to them, not what it costs you.
- **Two tiers.** No anchoring, no expansion path. Three is the minimum.
- **Five tiers.** Decision paralysis. Conversion drops. Three is the maximum for most B2B SaaS.
- **Hidden Tier 1.** No entry point = no PLG funnel = no expansion path. Always show a published low tier.
- **No annual discount.** Leaves cash and retention on the table. 15-20% annual is industry standard.
- **Per-seat pricing for non-user-driven products.** If automation consumes your product, per-seat is wrong.
- **No published Tier 3 price OR an absurdly high one.** "Contact us" works. "$50,000/month" published when most enterprise deals close at $80,000/year is a credibility kill.
- **Discount on demand.** Trains every future prospect to ask. Discount with structural reason or not at all.
- **Pricing changes between page and checkout.** Trust killer. Whatever's on the page is what they pay. Negotiate before the contract, not after.
- **Annual contract length without annual discount.** If you require annual upfront, you owe them a discount for the cash flow.
- **Pricing audit by feel.** Test changes with cohort data. Price increases need data to defend internally and externally.
- **Grandfathering forever.** Every customer at old pricing is a margin drag. Plan grandfathering with an end date.

---

## How to use the artifact downstream

After pricing is set:

1. **Update pricing page**, copy + tier structure + FAQ
2. **Train sales**, every rep memorizes the value math, discount rules, and negotiation playbook
3. **Update CRM products / SKUs**, clean structure for forecasting
4. **Update billing system**, Stripe / Chargebee / etc. with new tier definitions
5. **Communicate to existing customers**, if changing pricing, plan grandfathering window
6. **Test with 50-100 deals**, measure win rate, ASP, sales cycle changes vs. baseline
7. **Cross-reference comp plan**, pricing changes affect quota and OTE math (use `comp-plan-designer`)
8. **Cross-reference forecasting**, new tier mix changes pipeline math (use `forecasting-and-pipeline-review`)

---

**Pricing is a positioning decision dressed in numbers. Pick the strategy, design the tiers, anchor the high end, gate the right features, expand on the right axis, hold the line on discounts. The math comes after.**

---

_Part of the StackSwap Operator Playbook. → stackswap.ai/playbook_

Free forever. No email gate.