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pricing-strategy Structures pricing strategy decisions, packaging options, and pricing page design for SaaS and digital products. Use when reviewing or setting pricing, designing pricing tiers, evaluating freemium vs paid, or preparing a pricing change. Triggers on "pricing strategy", "pricing tiers", "freemium", "pricing page", "how should we price", "pricing change".

Pricing Strategy Skill

Build pricing that reflects value delivered — not cost to build. Structure every pricing decision with customer segmentation, value metric identification, competitive context, and a packaging recommendation.

Pricing Foundations

Three questions to answer before any pricing decision:

  1. Who is our buyer? (Role, company size, willingness to pay)
  2. What value do we deliver? (Quantifiable outcome — time saved, revenue generated, risk reduced)
  3. What is our pricing model? (Per seat, usage-based, flat, hybrid)

Pricing Models

Model Best For Risk
Per Seat Collaboration tools, team software Disincentivises adoption as team grows
Usage-Based APIs, infrastructure, consumption tools Revenue unpredictability for both sides
Flat Rate Simple tools, early-stage Leaves money on table from power users
Tiered Products with clear user segments Feature gatekeeping frustrates users
Freemium Viral/PLG products with low marginal cost Conversion to paid is hard to engineer
Value-Based Enterprise, outcomes-driven products Requires strong ROI story

Freemium Decision Framework

Use freemium when:

  • Marginal cost per free user is near zero
  • Product is inherently viral (network effects or sharing)
  • Free tier creates genuine value (not just a demo)
  • Clear upgrade trigger exists (feature, volume, or team size)
  • Conversion benchmark is realistic (25% free-to-paid is typical)

Avoid freemium when:

  • Support cost per free user is high
  • No natural upgrade trigger in the product
  • Core value requires features you'd need to gate

Packaging / Tiering Framework

Recommended 3-tier structure for SaaS:

Tier Target Price Signal Key Features Lock-in Mechanism
Free / Starter Individual, early discovery $0 Core value, usage-limited Invite colleagues, export limit
Pro / Growth SMB, growing teams $[X]/seat/mo Full features, higher limits Team collaboration, integrations
Business / Enterprise Mid-market, enterprise $[X]/seat/mo or custom Admin, SSO, SLAs, dedicated support Security, compliance, volume

Tier design rules:

  • Each tier should be genuinely sufficient for its target segment
  • The upgrade trigger should be felt naturally — not manufactured
  • Price jumps of 35x between tiers are normal and defensible

Competitive Pricing Context

Competitor Model Price Key Differentiator
[Name] [Model] [Price] [What they lead with]

Positioning options:

  • Premium: Price 2040% above market. Justify with enterprise features, support, or brand.
  • Parity: Match the market leader. Win on product or distribution.
  • Value: Price below market. Win on volume. Dangerous without strong unit economics.

Output Format

Pricing Strategy Recommendation — [Product] — [Date]

Current State: [What pricing exists today, if any] Problem to Solve: [Why pricing is being reviewed]

Recommended Pricing Model: [Model name + rationale]

Value Metric: [The single unit that scales with customer value — e.g., "active users", "API calls", "documents processed"]

Proposed Tiers:

[Table using 3-tier structure above]

Free-to-Paid Upgrade Trigger: [Specific moment or threshold that creates natural upgrade pressure]

Competitive Position: [Premium / Parity / Value + reasoning]

Pricing Change Rollout (if applicable):

  • Grandfathering: [Yes / No — recommendation and rationale]
  • Communication plan: [How to tell customers + timing]
  • Rollback plan: [Under what conditions you'd revert]

Risks:

  • [Risk] → Mitigation: [Action]

Metrics to Monitor Post-Change:

  • Conversion rate (free to paid)
  • Churn rate by tier
  • Average revenue per user (ARPU)
  • Expansion revenue

Guidelines

  • Never price based on cost — price based on value delivered to the customer
  • Always A/B test price changes where possible; use geographic holdouts if A/B isn't feasible
  • Recommend annual pricing with 1520% discount — improves cash flow and reduces churn
  • If enterprise pricing is "contact us", recommend adding a price floor to qualify inbound