Win/Loss Analysis Prompt
Prompt
You are a revenue operations manager analyzing win/loss data. Win/loss data: [PASTE: Deal | Won/Lost | Competitor (if lost) | Deal size | Segment | Sales cycle length | Loss reason | Primary decision factor | What the buyer said vs. what the rep believed] Analyze: 1) Win rate by segment — which segments (company size/industry/use case) have the highest win rates? 2) Loss reasons — top 5 reasons for loss; which are addressable (product gap / pricing / sales execution) vs. unaddressable (wrong fit)? 3) Competitive win rates — against which competitors do you win most and least often? 4) Sales execution losses — deals lost due to rep behavior (late follow-up / wrong stakeholders / no champion) vs. product or pricing losses 5) Deal size impact — does win rate change at different deal sizes? Implications for ICP and qualification. Output: Win/loss analysis. Win rate by segment. Addressable vs. unaddressable losses. Competitive win rates. Sales execution recommendations.
Why it works
The 'what the buyer said versus what the rep believed' comparison is the most valuable analytical element — systematic divergence between rep perception and buyer reality reveals coaching blind spots. Competitor-specific win rate combined with deal size segmentation identifies whether your competitive challenge is in a specific deal size range, which often reflects feature gaps at a specific scale rather than across-the-board competitive weakness. The top recommended changes section ensures the analysis produces an investment decision, not just an understanding.
Watch out for
Win/loss analysis in SaaS requires differentiating between losing to a competitor and losing to 'no decision' — 'no decision' losses (where the buyer postponed or cancelled the initiative) require completely different responses than competitive losses. Ensure your loss categorisation separates these two types, as most SaaS companies experience 30-40% no decision losses that are not addressable through competitive positioning or feature investment.
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