npx skills add ...
npx skills add github/awesome-copilot --skill gtm-technical-product-pricing
npx skills add github/awesome-copilot --skill gtm-technical-product-pricing
Pricing strategy for technical products. Use when choosing usage-based vs seat-based, designing freemium thresholds, structuring enterprise pricing conversations, deciding when to raise prices, or using price as a positioning signal.
Before recommending pricing, understand:
The Pattern:
Platform company, growth stage. Pricing hadn't changed since launch. Enterprise customers paying $15K/year for a product saving them $200K+ in engineering time.
Leadership debate: "If we raise prices, we'll lose customers."
What actually happened:
Raised enterprise tier from $15K to $45K/year. Added dedicated support, SSO, audit logs to justify the jump.
Lost: 0 enterprise customers. Zero.
Gained: 3x revenue per enterprise account. Plus the customers who stayed started taking the product more seriously — higher adoption, more internal champions, more expansion.
Why This Happens:
Technical founders anchor pricing to cost ("it costs us $X to serve them, so we charge $2X"). Enterprise buyers anchor pricing to value ("this saves us $200K, so $45K is cheap").
The Pricing Sanity Check:
For every customer segment, calculate:
How to Calculate Alternative Cost:
Common Mistake:
Comparing your price to competitors instead of to customer's alternative cost. Competitors anchor you to a race to the bottom. Value anchors you to what the customer actually saves.
Model 1: Seat-Based ($X/user/month)
Works when:
Breaks when:
Model 2: Usage-Based ($X/unit)
Works when:
Breaks when:
Model 3: Outcome-Based ($X/result)
Works when:
Breaks when:
The Hybrid That Usually Wins:
Platform fee (covers your fixed costs) + usage/outcome variable (scales with value).
Example: $500/month base + $0.05 per transaction (or API call, task completed, record processed — whatever your unit of value is).
Why this works:
The Pattern:
The hardest pricing decision for developer tools: where do you draw the line between free and paid?
The Framework: Find the Production Boundary
Free users who never pay are fine — they create awareness, community, and content. The problem is when production users never pay.
How to Find the Boundary:
Map your usage distribution:
Set your free tier limit just below where production usage starts. In this example: 1,000 units/month free.
Why: Hobbyists and learners stay free (they're your marketing engine). Production users hit the limit naturally and convert (they have budget).
The Three Types of Free-to-Paid Triggers:
1. Usage limit (most common for platforms)
2. Team/collaboration gate (best for tools)
3. Enterprise feature gate (best for platforms)
Common Mistake:
Setting free tier too high ("we want developers to love us"). If production users don't hit the limit, they never convert. Generosity in free tier should target learners, not production users.
The Pattern:
Enterprise pricing isn't a page on your website. It's a conversation. The "Contact Sales" button exists because enterprise deals have unique requirements — and because you should be pricing based on value, not a menu.
Enterprise Pricing Variables:
1. Deployment model (self-serve cloud, dedicated cloud, on-prem, hybrid)
2. Usage scale (seats, API volume, data volume)
3. Support level (community, standard, premium, dedicated)
4. Compliance requirements (SOC 2, HIPAA, FedRAMP, data residency)
The Enterprise Pricing Conversation:
When prospect says "what does it cost?":
Don't answer with a number. Answer with a question: "It depends on your deployment and scale requirements. Help me understand what you need."
Map their requirements:
Anchor to value before presenting price:
Present 3 options:
Common Mistake:
Publishing enterprise pricing on your website. The moment you publish a number, that's the ceiling — the negotiation only goes down from there. Keep enterprise pricing as a conversation.
The Pattern:
Your price tells buyers who you're for. This is as much a positioning decision as a revenue decision.
Price Signals:
$0 (Open source / free tier):
$20-100/month:
$500-2,000/month:
$5,000-50,000/year:
$100K+/year:
The Positioning Test:
If you price at $50/month but want enterprise customers, your price is undermining your positioning. Enterprise buyers associate low price with low value. You may need to raise prices to attract the customers you want.
Common Mistake:
Pricing for the customer you have instead of the customer you want. If your roadmap is enterprise, price for enterprise — even if it means losing some SMB customers today.
Timing Signals:
How to Raise Without Losing Customers:
1. Grandfather existing customers (12-24 months)
2. Add value to justify increase
3. Annual increase clause in contracts
The Communication:
"We're investing in [specific improvements]. To continue this level of investment, we're updating our pricing on [date]. Your current plan is locked in at your current rate until [grandfather date]."
Never apologize for raising prices. Frame it as investment in the product they love.
Based on pricing work at developer platforms and enterprise software companies, including enterprise price increases with zero customer loss, freemium threshold design that separated hobbyists from production users, partner pricing models, and pricing conversations across hundreds of enterprise deal cycles. Not theory — patterns from pricing decisions that directly impacted revenue.
Is value ratio > 5x for most customers?
├─ Yes → Raise prices
└─ No → Continue...
│
Are win rates > 40%?
├─ Yes → Price isn't the problem, but consider raising
└─ No → Continue...
│
Are you losing deals specifically on price?
├─ Yes → Don't raise. Improve value or segment better.
└─ No → Something else is wrong (product, positioning, sales)