Sales Win-Loss Analysis Framework
Market ResearchintermediateClaude 3.5 Sonnet or GPT-4o. Claude excels at pattern recognition across complex datasets and produces well-structured analysis. GPT-4o offers faster processing for large deal datasets. Both handle the multi-step analysis framework effectively.
When to Use This Prompt
Use this prompt quarterly or after significant deal cycles to understand market dynamics and competitive positioning. It's especially valuable when win rates are declining, losing to specific competitors repeatedly, or when you need to justify product roadmap priorities to leadership.
The Prompt
You are a strategic sales analyst helping a B2B [INDUSTRY] company understand why they win and lose deals. I'm providing you with deal data and customer feedback to identify patterns.
## Your Task
Analyze the following win-loss data and produce:
1. **Key Win Factors** - Top 3-5 reasons customers chose us
2. **Critical Loss Factors** - Top 3-5 reasons we lost deals
3. **Competitive Positioning** - How we compare to main competitors
4. **Segment Insights** - Patterns by company size, industry, or geography
5. **Actionable Recommendations** - Specific changes for sales, product, and marketing
## Data to Analyze
**Company Profile:**
- Product/Service: [YOUR_PRODUCT]
- Target Market: [TARGET_SEGMENT]
- Average Deal Size: [DEAL_SIZE]
- Sales Cycle: [CYCLE_LENGTH]
**Won Deals Summary (Last [TIME_PERIOD]):**
- Total Won: [NUMBER]
- Average Deal Value: [VALUE]
- Top 3 Customer Reasons for Choosing Us: [REASONS]
- Common Customer Titles: [TITLES]
**Lost Deals Summary (Last [TIME_PERIOD]):**
- Total Lost: [NUMBER]
- Lost to Competitors: [COMPETITOR_NAMES]
- Top 3 Customer Reasons for Not Choosing Us: [REASONS]
- Price Sensitivity: [HIGH/MEDIUM/LOW]
**Customer Feedback Themes:**
[PASTE 3-5 REPRESENTATIVE CUSTOMER QUOTES OR FEEDBACK SUMMARIES]
## Analysis Requirements
- Identify patterns across deal size, industry vertical, and geography
- Distinguish between price objections and value objections
- Assess product gaps vs. sales/marketing execution gaps
- Rank recommendations by impact and implementation difficulty
- Highlight quick wins vs. long-term strategic changes
## Output Format
Structure your analysis with clear sections, bullet points, and a prioritized recommendation matrix that includes effort level and expected impact.
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Tips for Best Results
- 1.Include actual customer quotes or feedback snippets in the data section—AI analysis improves significantly with direct voice-of-customer input rather than summaries.
- 2.Segment your win-loss data by deal size, industry, and geography before analysis—patterns differ dramatically and generic insights miss critical opportunities.
- 3.Add competitive intelligence about competitor pricing, features, and positioning—this context helps AI identify realistic differentiation strategies.
- 4.Request a prioritized recommendation matrix with effort/impact scoring—this forces actionable output and helps you sequence changes based on resources available.
Example Output
## Win-Loss Analysis Summary: Enterprise SaaS Platform
### Key Win Factors
1. **Integration Ecosystem** (45% of wins) - Customers valued pre-built connectors to existing tools
2. **Ease of Implementation** (38% of wins) - Fast time-to-value with minimal IT overhead
3. **Customer Support Quality** (32% of wins) - Responsive, knowledgeable support team
4. **Transparent Pricing** (28% of wins) - No surprise costs or complex licensing
5. **Security Compliance** (25% of wins) - SOC 2, HIPAA, GDPR certifications
### Critical Loss Factors
1. **Price Premium** (52% of losses) - Positioned 25-40% higher than primary competitors
2. **Feature Gaps** (38% of losses) - Missing advanced reporting and custom workflows
3. **Incumbent Switching Costs** (35% of losses) - Customers reluctant to migrate from legacy systems
4. **Sales Cycle Length** (22% of losses) - 6-month process lost to faster-moving competitors
5. **Limited Mobile Functionality** (18% of losses) - Mobile app lacked desktop feature parity
### Competitive Positioning
- **vs. Competitor A**: We win on support and UX; lose on price and feature breadth
- **vs. Competitor B**: We win on security and compliance; lose on market presence and brand recognition
- **vs. Competitor C**: We win on implementation speed; lose on advanced customization options
### Segment Insights
- **Mid-Market (100-1000 employees)**: Highest win rate (62%); price-sensitive but value implementation speed
- **Enterprise (1000+ employees)**: Lower win rate (38%); require advanced features and custom integrations
- **Financial Services**: 71% win rate; compliance and security drive decisions
- **Healthcare**: 45% win rate; feature gaps in patient data workflows causing losses
### Top Recommendations
| Recommendation | Owner | Impact | Effort | Timeline |
|---|---|---|---|---|
| Develop advanced reporting module | Product | High | High | Q3-Q4 |
| Create competitive battle cards | Sales | Medium | Low | 2 weeks |
| Implement mobile feature parity | Product | Medium | High | Q2-Q3 |
| Launch value-based pricing model | Marketing | High | Medium | 6 weeks |
| Establish customer advisory board | Customer Success | Medium | Low | 4 weeks |
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