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
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.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
How It Works
Internal Interviews (Sales Reps)
Automated Slack Interviews- When a deal closes, Hindsight automatically sends a personalized interview request via Slack
- Questions are tailored based on the deal’s context (calls, notes, CRM data)
- Reps have a natural conversation that takes 1-2 minutes
- The AI conducts follow-up questions based on responses
- Interview transcripts are automatically imported and analyzed
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
- Different email variants for A/B testing
- Delayed send timing
- Approval workflows
- Response rate tracking
Setup and Configuration
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
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
What You Get
Rich Deal Insights
- Decision drivers — Understand what really influenced the outcome
- Competitive intelligence — Learn how you stack up against competitors
- Product feedback — Discover feature gaps and strengths
- Pricing insights — See how prospects really view your pricing
Actionable Outputs
The interview data feeds directly into creating:- Battle cards — Competitive positioning based on real feedback
- Messaging guides — What resonates with different buyer types
- Product roadmaps — Feature requests and pain points
- Sales coaching — Real examples of what works and what doesn’t
Best Practices
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)
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
Getting Started
- Enable win-loss interviews in your Hindsight settings
- Customize email templates for external outreach
- Set up Slack integration for internal interviews
- Configure timing and approval workflows
- Start with a small test group to refine your approach
- Scale to all deals once you’re satisfied with the process