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How to do Sales Opportunity Win/Loss Analysis

Written by Team Enterpret

You've connected your sales data to Enterpret - now it's time to understand why you're winning and losing deals. This guide will show you how to build comprehensive win/loss analysis dashboards that reveal competitive dynamics, feature gaps, and opportunity patterns.

Before You Start: Understanding Your Data Structure

Every company tracks sales data differently. Before building your dashboard, find out where these key data points exist in your metadata:

Deal Information:

  • Win/loss status (e.g., Stage, Outcome, Status fields)

  • Deal values (e.g., ARR, Contract Value fields)

  • Deal types (e.g., New Business, Expansion)

Account Information:

  • Account identifiers

  • Segment/industry data

  • Account size indicators

Sales Conversation Data:

  • Source platform (e.g., Gong, Chorus)

  • Call/meeting timestamps

  • Participant information

Pro Tip: Review your metadata fields in the Integrations page to identify these key fields for your account.

Step-by-Step Guide

Setup Basic Volume Tracking

Create a Quantify to track closed-lost conversations:

Plot: Feedback Records

Filters:
Opportunity Stage = "Closed Lost" (or your equivalent field)
Source = CRM/Your sales conversation platform

Duration: Last 3 months

View: Trend chart

This lets you see if your lost deal volume is increasing or decreasing over time.

Always filter using your CRM fields (like Salesforce Opportunity Stage) to determine won/lost status, rather than relying on mentions in sales conversations.( Gong, Chrous)
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This ensures you're analyzing deals that are officially closed, not just ones where winning or losing was discussed.

Compare Win vs Loss Patterns

Basic Win/Loss Comparison

Create a Quantify to compare feedback patterns between won and lost deals:

Plot: Reasons

Filters:
Source = Your sales conversation platform
AND Deal Status = "Closed Won" OR "Closed Lost"

Duration: Last 3 months

View: Bar chart

Then click "Compare" and choose "By Another Filter":

Filter A: Deal Status = "Closed Won" (using your CRM field name)
Filter B: Deal Status = "Closed Lost" (using your CRM field name)

This will show two bars for each Reason - one showing frequency in won deals, one showing frequency in lost deals.

What this helps us understand:

  • Which topics come up more frequently in won vs lost deals

  • Key differentiators that help close deals

  • Common objections in lost opportunities

Pro Tip: Use the "Compare" feature to create a clear visual distinction between won and lost deal patterns.

Analyze Competitive Dynamics

Competitor Mention Analysis

Create a Quantify to track competitor mentions in lost deals:

Plot: Keywords (filter to Competitor category)

Filters:
Deal Status = "Closed Lost"
Source = Your sales conversation platform

Duration: Last 3 months

View: Bar chart

Feature Comparison by Competitor

Create a Quantify to understand feature discussions when competitors are mentioned:

Plot: Reasons

Filters:
Deal Status = "Closed Lost"
AND Keyword is any of [Your competitor keywords]

Duration: Last 3 months

View: Bar chart

What this helps us understand:

  • Which competitors you're losing to most frequently

  • Feature gaps compared to specific competitors

  • Common competitive differentiation points

Track Deal Stage Patterns

Stage-Based Analysis

Create a Quantify to understand feedback patterns at different deal stages:

Plot: Deal Stage (your equivalent field)

Filters:
Deal Status = "Closed Lost"
Duration: Last 3 months

View: Bar chart

What this helps us understand:

  • When in the sales cycle deals typically fall through

  • Different objection patterns at each stage

  • Opportunities for earlier qualification

Pro Tip: Look for anomalies in stage patterns - unusual spikes in losses at certain stages might indicate process issues.

Monitor Feature Gaps

Feature Request Tracking

Create a Quantify to identify missing features impacting deals:

Plot: Reasons (filter to Improvement category)

Filters:

Deal Status = "Closed Lost"
Duration: Last 3 months

View: Bar chart

Compare: Against previous period

What this helps us understand:

  • Most requested missing features

  • Trending feature gaps

  • Priority areas for product development

Detect Emerging Patterns

Anomaly Detection

Set up trend monitoring with anomalies enabled:
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Plot: Reasons

Filters:

Deal Status = "Closed Lost"
Duration: Last 3 months

View: Trend chart with anomalies

Enable anomaly detection

What this helps us understand:

  • Sudden changes in loss reasons

  • Emerging competitive threats

  • New feature gap patterns

Pro Tip: Set up regular dashboard subscriptions to stay on top of changing patterns in your win/loss analysis.


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Common Questions

Q: How do I handle deals with multiple loss reasons?

A: Enterpret automatically tracks all mentioned reasons. Focus on patterns and trends rather than exact counts.

Q: What's the right time period to analyze?

A: Start with 3 months and adjust based on your sales cycle length and deal volume.

Q: How should I share these insights with stakeholders?

A: Use the dashboard sharing feature and set up regular email/Slack updates for key insights.

Need Help with setting this up?

  • Contact us for assistance with setup

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