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Overview

Use AI to analyze your closed deals to generate structured win-loss insights. AI analyzes all your deal documents, CRM data, and conversations to create detailed deal stories with actionable recommendations.

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How Deal Analysis Works

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Data Sources Processing

Hindsight analyzes multiple data sources from each deal:
  • CRM Properties: Deal stage history, custom fields, and opportunity data
  • Meeting Recordings: Gong calls, Zoom transcripts, customer conversations
  • Deal Documents: Proposals, contracts, emails, notes, and attachments
  • Win-Loss Interviews: Structured feedback from buyers and internal teams
Deal data is synced automatically every 12 hours for the deals you select to import for analysis. Auto-import rules can be configured to automate the win-loss analysis process end-to-end.

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Outputs

For every analyzed deal, Hindsight creates a comprehensive deal story containing:
  • Executive Summary
  • Timeline
  • Stakeholders
  • Decision Drivers Analysis
  • Competitive Landscape
  • Key Quotes & Evidence
  • Lessons Learned & Recommendations

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Structured Insights Extraction

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Decision Driver Analysis

Hindsight maps deal conversations to your organization’s decision drivers:
  • Automated Detection: AI identifies mentions of your configured decision drivers
  • Sentiment Analysis: Positive, negative, or neutral perception of each driver
  • Impact Scoring: Relative importance of each driver in the decision
  • Supporting Evidence: Specific quotes and context for each driver

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Feature Tracking

Track which product capabilities influenced the deal:
  • Feature Mentions: Automatic detection of product feature discussions
  • Customer Sentiment: How buyers perceived specific capabilities
  • Competitive Context: Features compared against competitor offerings

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Competitive Intelligence

Comprehensive competitor analysis for every deal:
  • Competitor Identification: Automatic detection and tagging of competitors
  • Precision Tagging: Automatically classify if competitors were incumbents, primary, or secondary
  • Outcome Classification: Whether competitors were mentioned, evaluated, or selected
  • Positioning Analysis: How competitors were positioned vs. your solution

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Custom Insights:

Create custom prompts to extract specific insights:
  • Metrics: AI evaluates deals against a 1-5 scale rubric
  • Answers: Free-form answers with configurable prompts, length, and format

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CRM Integration & Sync-Back

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Automated CRM Updates

Hindsight automatically syncs insights back to your CRM
  • Win/Loss Reasons: Populate standardized win/loss reasons
  • Deal Summary: Executive summary in deal notes
  • Competitors: Update competitor fields with detected competitors
  • Features: Populate features discussed in the deal
  • Custom Fields: Sync custom metrics and answers to CRM fields
Requires HubSpot or Salesforce integration with Admin / Write access.

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Analysis Triggers & Automation

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Automatic Analysis

Deals are automatically analyzed when:
  • Deal stage changes to “Closed Won” or “Closed Lost”
  • Deal meets auto-import criteria (configured in settings)
  • New deal data is available (win-loss interviews, CRM properties)

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Manual Analysis

You can also trigger analysis manually:
  • For deals that need re-analysis after new information
  • To focus on specific decision drivers or competitors
  • When filtering by particular document types
  • For historical deals that weren’t previously analyzed

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Automated Feedback Collection

Collect feedback from stakeholders with automated win-loss interviews:
  • Internal team feedback requests via Slack and email
  • External buyer feedback through automated surveys

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Getting Started with Deal Reviews

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Setup Requirements

  1. CRM Integration: Connect HubSpot or Salesforce for deal data
  2. Analysis Configuration: Configure your organization’s Drivers, Features, and Competitors