Guides marketers through designing, executing, and activating win/loss analysis programs — from CRM audits and interview design to stakeholder alignment and executive reporting.
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# Win/Loss Analysis
## Overview
This skill covers how to build and run effective win/loss analysis programs, including CRM-based pipeline audits, structured interview design, participant recruitment, stakeholder alignment, and translating findings into action. All practices are sourced exclusively from Exit Five podcast guests across 8 episodes. No general best practices have been added beyond what guests explicitly recommended.
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## Starting a Win/Loss Program
**Launch with a retrospective pilot before building an ongoing program.**
Start by looking back at deals from the previous two quarters rather than waiting for new deals to close. Run a focused six-week sprint targeting a specific business goal — entering a new market, validating a product thesis, or understanding a key customer segment. This gives you a larger deal pool to recruit from, proves value quickly, and builds momentum for an ongoing program. After the pilot, transition to ongoing win/loss on new deals. (Source: Drew Giovannoli, Episode #221)
**Align program timing with key business events.**
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The line at the top of this page pins the label v2026-04-21, which is what most people want. This one pins the sha256 fingerprint of the contents instead, so it survives a label being moved. Either way the exact version is written to mdr.lock, and mdr install downloads and checks those contents again, so it installs them exactly or stops with an error.
GET https://markdownregistry.com/api/v1/artifacts/art_5ujd7ah7rbjphune
GET https://markdownregistry.com/api/v1/resolve?ref=the-nam-shub/e5-real-skills/win-loss-analysis
GET https://markdownregistry.com/api/v1/blob/bf94c97c2b341828c7b4e945c1a77e4a1d332433257cf3b7b56d557ae034eec4
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modest-curator478/claude-skills · revops/win-loss-analysis/SKILL.md · AUTO-TRIGGER: Apply this skill when the user wants to run, structure,
or improve a win/loss analysis program. Trigger…
