Am I winning or losing more deals than I’m closing?
You close deals. You lose deals. But do you know the ratio, and more importantly, is it getting better or worse? Here's how to track your win/loss balance.
The short answer
Count Closed Won and Closed Lost deals for each month. The ratio tells you whether you're winning more than you're losing. But also check the volume: are you resolving enough deals each month, or are most deals sitting open indefinitely? A healthy pipeline has a steady flow of resolutions, not just a growing stack of open opportunities.
Win/loss ratio reveals more than close rate alone
Your close rate might be 30%. But that number doesn't tell you whether the trend is improving or declining. It doesn't tell you whether you're losing more deals this quarter than last. And it doesn't tell you whether the deals you're losing are bigger or smaller than the ones you're winning.
A win/loss analysis by month shows the trajectory. If you won 8 and lost 4 in January but won 5 and lost 9 in March, something changed. Your close rate might have only dropped a few points, but the deal outcome balance flipped. That's a warning sign you need to investigate before it becomes a revenue problem.
Deal outcome metrics to track monthly
- Deals won vs. deals lost (count). Simple ratio by month. Is the trend improving?
- Revenue won vs. revenue lost (dollars).You might win 8 deals worth $60K total but lose 4 deals worth $120K. The count looks good. The dollars don't.
- Resolution rate.What percentage of pipeline is being resolved (won or lost) each month vs. sitting open? If you have 50 open deals and only resolve 5 per month, deals are piling up faster than they're being worked.
- Lost reasons trend.Are the same reasons showing up? “Budget” three months in a row means a pricing or qualifying problem. “Went with competitor” trending up means your positioning or timing is slipping.
How to track win/loss balance in HubSpot
- 1Go to Reports → Analytics Tools → Sales Analytics
Select Deals closed vs. goal or Deal close rate from the sidebar. Set the date range to the last 6 months. This shows won and lost deals by month with the ratio.
- 2Check revenue values, not just counts
In the Deals view (Sales → Deals), switch to List view. Filter for “Deal stage is Closed Won” and note the total amount. Then filter for “Closed Lost” and note that total. Compare the dollar values, not just the deal counts.
- 3Review lost reasons
In Sales Analytics, select Deal lost reason analysis. This groups lost deals by reason. Look for patterns: if one reason is growing as a percentage over time, that's the root cause to address.
Total time: 10-15 minutes. The counts are quick. Getting the dollar-weighted view requires filtering in the Deals list.
How to track win/loss balance in Salesforce
- 1Create a Won vs. Lost report
Go to Reports → New Report → Opportunities. Filter for Closed Won and Closed Lost in the last 6 months. Group by “Stage” (which separates won and lost). Summarize Amount as Sum and Record Count. Group secondarily by Close Date (month) to see the trend.
- 2Add loss reasons
Filter for Closed Lost only. Group by the “Loss Reason” field. If this field isn't populated, that's a data quality issue to fix. Without reasons, you can't diagnose why you're losing.
- 3Check the resolution rate
Count total resolved deals (Won + Lost) per month. Compare to the total deals in your pipeline. If you have 80 open deals and resolve 10 per month, your pipeline is 8 months deep. That probably means most of those deals are dead but not marked as such.
Total time: 15-20 minutes. One custom report for win/loss balance. A separate filter for loss reasons.
Validate wins against actual invoices
A “win” in your CRM should produce an invoice in your accounting software. If you won 8 deals this month but only 6 invoices appeared in QuickBooks or Xero, 2 wins either fell through, changed scope, or were never billed. Cross-referencing ensures your win count reflects actual revenue, not just CRM stage changes.
Monthly effort for win/loss tracking
About 15 minutes to pull the numbers. The harder part is discipline: making sure reps close dead deals as Lost (with reasons) instead of leaving them open. Without that, your loss count is understated and your win/loss ratio is artificially inflated.
Or get your win/loss balance tracked every month
Bottomline tracks deal outcomes by count and by dollar value, monitors the trend, and cross-references wins with actual invoicing.
Warning: You're winning more deals by count but losing bigger deals by dollar value. Average lost deal is 2.4x average won deal.
The insight that matters most: are you winning by count but losing by dollars? Bottomline catches this pattern automatically and surfaces it before it becomes a revenue problem.