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How to do Sales Opportunity Win/Loss Analysis
How to do Sales Opportunity Win/Loss Analysis
Team Enterpret avatar
Written by Team Enterpret
Updated over 2 weeks ago

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)

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:

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.


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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