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Most teams rely on reps to fill out dropdown lists and type notes when deals close. This approach has several problems:
  • Inaccurate data — Reps rush through forms or forget details
  • Biased responses — Self-reporting creates inherent bias
  • Hard to act on — Generic fields don’t capture nuanced insights
  • Incomplete coverage — Only covers deals reps remember to update

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How Hindsight Solves This

Hindsight makes win-loss analysis effortless by automating personalized interviews for every deal. The AI analyzes your calls, CRM data, emails, and notes to understand each deal’s context, then conducts tailored interviews with your team. Win-loss interviews are one of the most valuable data sources for strategic decision-making. With Hindsight’s automation, you can get comprehensive, unbiased insights from every deal without manual overhead or wasting your reps’ time.
  1. Hindsight verifies data by comparing multiple data sources
  2. Hindsight identifies gaps in your win-loss data and crafts personalized questions
  3. Hindsight conducts quick, natural conversations with reps via Slack to fill in said gaps

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Key Benefits

  • Complete coverage — Interview every deal, not just a sample
  • Unbiased insights — AI pulls objective insights without human bias
  • Personalized questions — Context-aware interviews based on deal specifics
  • Quick for reps — 1-2 minute conversations vs lengthy CRM forms
  • Actionable data — Rich insights you can actually use for strategy

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How It Works

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Internal Interviews (Sales Reps)

Automated Slack Interviews
  1. When a deal closes, Hindsight automatically sends a personalized interview request via Slack
  2. Questions are tailored based on the deal’s context (calls, notes, CRM data)
  3. Reps have a natural conversation that takes 1-2 minutes
  4. The AI conducts follow-up questions based on responses
  5. Interview transcripts are automatically imported and analyzed

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External Interviews (Prospects)

Email Outreach
  • Send automated email sequences to prospects after deals close
  • Customizable templates with different incentive levels
  • Prospects can click a link for a quick survey or schedule a live interview
Customization Options:
  • Different email variants for A/B testing
  • Delayed send timing
  • Approval workflows
  • Response rate tracking

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Setup and Configuration

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Interview Settings

  • Email templates — Customize outreach copy and incentives
  • Timing controls — Set delays for when interviews are sent
  • Approval workflows — Route requests through reps and managers if needed
  • Variants — Test different approaches to improve response rates

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Analytics and Optimization

  • Track response rates across different variants
  • Monitor which approaches get the best engagement
  • A/B test templates and timing to improve the process over time

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Best Practices

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For Internal Interviews

  • Get feedback from multiple perspectives (reps, SEs, managers, etc.)
  • Get feedback as soon as possible after deal close
  • Keep interviews short and focused (1-2 minutes)

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For External Interviews

  • Time outreach appropriately (not immediately after a loss)
  • Have reps and other relationship owners send the emails and introduce the process
  • Offer meaningful incentives for participation
  • Keep surveys short and focused