Win/Loss Analysis Program

Create a win/loss interview template with 10-15 questions covering decision criteria, evaluation process, competitors considered, why you won/lost, pricing perception, champion strength, objections encountered.

Identify 5 recent closed deals (3 wins, 2 losses); schedule 20-30 minute interviews with key stakeholders (champion, economic buyer, or evaluator) within 2 weeks of close.

Set pass threshold: complete interviews for >=4 out of 5 deals, and identify >=3 actionable insights (sales process improvements, product gaps, positioning opportunities, competitive intel).

During interviews, ask open-ended questions: "What made you choose us?" "What almost made you not choose us?" "How did we compare to [competitor]?" "What could we have done better?" Take detailed notes.

For wins, understand what worked: Which features mattered most? Was pricing competitive? Was sales process smooth? Was champion strong? Use insights to replicate in future deals.

For losses, diagnose why: Missing feature? Too expensive? Competitor advantage? Weak champion? Poor sales execution? Identify if loss was preventable or unwinnable.

Log win/loss data in Attio with fields for primary_win_reason, primary_loss_reason, competitors_evaluated, decision_criteria, and actionable_insights; tag insights by category (product, pricing, sales process, competitive).

In PostHog, create events for deal_closed_won and deal_closed_lost with properties for win/loss reasons; track patterns over time.

After 1 week, synthesize findings: Are you losing on price? Specific features? Sales execution? Compile top 3 insights and share with team.

If >=4 interviews completed and >=3 actionable insights identified, win/loss analysis is valuable; document interview process and proceed to Baseline; otherwise refine questions or improve stakeholder access.