AI Win/Loss Decoder: Automate Post‑Mortems to Turn Every Deal into a Playbook

Bob interviews a practitioner who built an "AI Win/Loss Decoder" — a lightweight, revenue-focused pipeline that ingests call transcripts, proposals, emails, and CRM notes to reveal why deals won or lost and then auto-generates repeatable playbooks, objection responses, and next-step sequences. This episode walks through exact data sources, simple labeling approaches, prompt patterns, and human-in-the-loop checks so listeners can start with 50–200 historical deals and get meaningful insights fast. You’ll hear concrete examples of playbooks one advisor deployed, the validation metrics they used, and a pragmatic rollout plan that fits a solo operator or small team. The conversation teaches a replicable method, solves the mystery of inconsistent sales outcomes, and gives a clear, actionable path to turn existing deal history into predictable revenue.