SKILL.md
Pricing Strategist
Expert pricing strategy and monetization guidance for SaaS and digital products — from psychology-driven pricing to enterprise negotiation tactics.
Philosophy
Pricing is the most powerful lever in your business:
- Price is a signal — It communicates value, market position, and customer fit
- Packaging is product — How you bundle features shapes perceived value
- Simplicity wins — Confused buyers don't buy
- Test everything — Intuition about willingness-to-pay is usually wrong
How This Skill Works
When invoked, apply the guidelines in rules/ organized by:
psychology-* — Behavioral economics, anchoring, framing, decoy pricing
packaging-* — Tier structure, bundles, good/better/best frameworks
metrics-* — Value metrics, usage-based, per-seat, flat-rate models
page-* — Pricing page copy, design, and conversion optimization
enterprise-* — Enterprise pricing, negotiation, custom deals
lifecycle-* — Discounts, promotions, price increases, grandfathering
Core Frameworks
The Pricing Stack
┌─────────────────────────────────────────────────────────┐
│ VALUE CREATION │
│ What problem do you solve? How well? │
├─────────────────────────────────────────────────────────┤
│ VALUE COMMUNICATION │
│ How do you convey value through pricing? │
├─────────────────────────────────────────────────────────┤
│ VALUE CAPTURE │
│ How much value do you extract as price? │
└─────────────────────────────────────────────────────────┘
Pricing Model Comparison
| Model |
Best For |
Pros |
Cons |
| Per-seat |
Collaboration tools |
Predictable, scales with adoption |
Discourages sharing |
| Usage-based |
Infrastructure, API |
Aligns with value, low entry |
Unpredictable revenue |
| Flat-rate |
Simple products |
Easy to understand |
Leaves money on table |
| Tiered |
Most SaaS |
Captures segments |
Can be complex |
| Hybrid |
Mature products |
Flexible, optimized |
Harder to communicate |
Value Metric Selection
Your value metric should be:
| Criteria |
Question |
Example |
| Easy to understand |
Can you explain it in 5 words? |
"Pay per user per month" |
| Aligned with value |
Does customer pay more as they get more value? |
More emails sent = more conversions |
| Predictable |
Can customer forecast their bill? |
Seat count is predictable |
| Scalable |
Does it grow with the customer? |
API calls scale with usage |
The Willingness-to-Pay Curve
High WTP │ ●●● Enterprise
│ ●●●●●
│ ●●●●●●● Pro
│ ●●●●●●●●●
│●●●●●●●●●●● Starter
Low WTP │●●●●●●●●●●●●●
└────────────────────
Few Many
Customers
Capture value at each segment with differentiated packaging.
Pricing Psychology Principles
| Principle |
How It Works |
Application |
| Anchoring |
First price sets expectations |
Show enterprise price first |
| Decoy effect |
Third option makes one look better |
Middle tier becomes attractive |
| Charm pricing |
9-ending feels cheaper |
$99 vs $100 |
| Price partitioning |
Split price seems smaller |
$50/mo + $20 support |
| Round numbers |
Feel more premium |
$1,000 for enterprise |
Packaging Framework
Good/Better/Best Structure
| Tier |
Target |
Feature Strategy |
Pricing |
| Good (Starter) |
Entry-level, price-sensitive |
Core features, limited usage |
Low anchor |
| Better (Pro) |
Growth, main target |
Full features, higher limits |
Optimal margin |
| Best (Enterprise) |
High-value, complex needs |
Unlimited, premium support |
Value-based |
Feature Fencing Strategies
| Strategy |
Description |
Example |
| Usage limits |
Cap quantity/volume |
1,000 vs 10,000 emails |
| Feature gates |
Reserve features for higher tiers |
SSO in Enterprise |
| Support tiers |
Differentiate service level |
Email vs dedicated CSM |
| SLA guarantees |
Higher uptime commitments |
99.9% vs 99.99% |
| Integration access |
Limit connection types |
Basic vs premium integrations |
Annual vs Monthly Framework
| Factor |
Monthly |
Annual |
| Discount |
Baseline |
15-20% off (2 months free) |
| Cash flow |
Spread out |
Upfront capital |
| Churn |
Higher (monthly exit) |
Lower (commitment) |
| Target |
Skeptics, small biz |
Confident, enterprise |
| Positioning |
"Flexibility" |
"Best value" |
Anti-Patterns
- Race to bottom — Competing on price alone destroys margins
- Complexity overload — 6+ tiers confuse buyers
- Feature stuffing — More features ≠ higher perceived value
- Discount addiction — Training customers to wait for sales
- One-size pricing — Leaving money on table from high-value customers
- Hidden fees — Surprise charges destroy trust
- Anchoring backwards — Showing cheapest option first
- Ignoring segments — Same price for SMB and enterprise