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Overview

Hindsight’s automated win-loss interview system helps you systematically collect feedback from both buyers and sellers after deals close. The platform automatically identifies closed deals, sends customized interview requests, conducts AI-powered interviews, and analyzes responses to provide actionable insights.

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Key Features

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Automated Interview Triggers

  • Deal-Based Filtering: Automatically trigger interviews based on deal stage, amount, owner, or custom criteria
  • Smart Timing: Configurable delays to send interviews at optimal times after deal closure

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Multi-Channel Collection

  • Email Automation: Customizable email sequences with professional templates
  • Slack Interviews: Conduct interviews directly in Slack with voice transcription support
  • Survey Links: Generate shareable survey links for AI interviews in a web interface
  • A/B Testing: Test multiple outreach sequence variants to optimize response rates

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AI-Powered Interviews

  • Personalized: Interviews are deeply personalized based on insights from Deal Reviews and contact information
  • Conversational AI: Natural language interviews that adapt based on responses
  • Voice Support: Record and transcribe voice responses through Slack
  • Smart Follow-ups: AI asks relevant follow-up questions based on initial responses

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Setting Up Automated Interviews

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External Buyer Interviews

Configure automated feedback collection from buyers and prospects in (Settings)[https://app.usehindsight.com/settings/reports]: 
// Example deal filter configuration
{
  dealStage: ["Closed Won", "Closed Lost"],
  dealAmount: { min: 10000 },
  dealOwner: "[email protected]", // Optional
  customField: "enterprise_deal" // Optional
}
Email Customization Options:
  • Custom subject lines and email content
  • Personalized sender (we recommend PMs or leadership, not sales reps)
  • Email threading to maintain conversation context
  • Link included in email to complete the interview
  • Automated reminder sequences
Response Collection:
  • Completed interviews are transcribed, uploaded to Hindsight, and analyzed automatically
  • Slack-based interviews with voice support are handled similarly

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Internal Seller Interviews

Automate feedback collection from your sales team: Slack Integration:
  • Automatic requests in Slack when deals close
  • Voice recording capabilities through Slack
  • Real-time transcription using AI
  • Integration with Deal Review workflows
Email Workflows:
  • Customizable templates for different deal types
  • Automated follow-ups for incomplete responses
  • Thread management for organized communication

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Interview Customization

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Email Templates

Create multiple email variants to optimize response rates, for example:
  • Professional Templates: Formal business communication style
  • Casual Templates: Friendly, conversational tone
  • Industry-Specific: Tailored messaging for different verticals
  • Follow-up Sequences: Gentle reminders with varying messaging

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AI Interview Personas

Customize the AI interviewer based on your needs:
  • Conversational Style: Formal vs. casual tone
  • Question Focus: Technical details vs. business impact
  • Follow-up Depth: Surface-level vs. deep-dive questioning

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Slack Integration

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Setup Requirements

  1. Slack App Installation: Install Hindsight bot in your workspace

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Voice Interview Features

Recording Capabilities:
  • High-quality voice recording through Slack
  • Automatic transcription using Groq Whisper AI
  • Support for multiple languages and accents
  • Noise reduction and audio enhancement

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Response Analysis

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Automatic Processing

All interview responses are automatically:
  • Transcribed: Voice converted to text for analysis
  • Categorized: Responses sorted by themes and topics
  • Analyzed: AI extracts key insights and patterns
  • Documented: Stored as structured deal documents

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Integration with Deal Analysis

Interview responses integrate seamlessly with:
  • Deal Review Reports: Include feedback in comprehensive deal analysis
  • Competitive Intelligence: Extract competitor mentions and comparisons
  • Feature Feedback: Identify product improvement opportunities
  • Win-Loss Patterns: Build understanding of success factors

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Success Measurement

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Response Rate Optimization

Track and improve interview participation: Email Metrics:
  • Response rates by email variant
  • A/B test performance
Survey Metrics:
  • Completion rates by survey length
  • Follow-up effectiveness

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Best Practices

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Timing Strategy

For Won Deals:
  • Send within 1-2 weeks of deal closure
  • Allow time for implementation discussion
  • Capture fresh memories while maintaining relationships
For Lost Deals:
  • Send immediately after loss notification
  • Maintain professional tone
  • Focus on future relationship building

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Email Effectiveness

Before Sending Requests
  • For external requests, try to have the sales rep send a personal note explaining that they will receive a request
  • Include context about the interview purpose and importance
  • For internal requests, ensure the sales team understands the value of providing feedback during trainings and win-loss insights shareouts
Subject Line Optimization:
  • Include deal/company reference
  • Avoid “survey” language
  • Use personal, conversational tone
  • A/B test different approaches
Content Best Practices:
  • Keep initial request brief
  • Explain value for respondent
  • Offer multiple response options
  • Include clear next steps
The win-loss interview system transforms post-deal activities from manual, inconsistent processes into systematic, data-driven insights that improve your entire sales and product strategy.