How to Get Sales Teams On Board with Win/Loss Analysis
When a software company launches a win/loss program and an external firm is introduced, sales teams may feel some trepidation. There’s a natural concern that the process could be used to point fingers or uncover feedback that feels personal or critical.
That hesitation is understandable. Salespeople invest tremendous time, energy, and emotion into every opportunity. But when win/loss analysis is positioned as a learning tool, not a judgment exercise, it becomes a powerful resource for the team’s continual improvement and shared success.
Reframing Win/Loss as a Sales Enablement Tool
Of course, the biggest reason for sales teams to embrace a win/loss program is that it helps them get better at closing deals and increasing the win rate.
In enterprise sales, deals are often complex and carry high stakes. Long sales cycles, large buying groups, and savvy competitors make it essential to understand exactly why you win or lose a deal.
How Win/Loss Insights Help Sales Close More Deals
When they hear directly from prospects and customers, sales teams can use this intel to:
learn what they could have done differently to win the business
understand what competitors did
provide unbiased data back to other departments such as marketing, product and customer success
sometimes go back and still win the business!
The ROI of a Structured Win/Loss Program
This impact is more than just anecdotal.
According to Gartner’s report “Tech Go‑to‑Market: Three Ways Marketers Can Use Data From Win/Loss Analysis to Increase Win Rates and Revenues” (Todd Berkowitz, May 2014), companies that run win/loss programs in a structured, systematic way can see up to a 50% increase in win rates and a 15–30% increase in revenue.
Gartner recommends having an independent party do the analysis – rather than the sales team – so that feedback is objective, unbiased, and more actionable.
Simple Steps to Build Sales Buy-In for Win/Loss
At IcebergIQ, we have identified a few ways to build buy-in for a win/loss program and set the sales team up for success.
Ask the team to flag deals and suggest questions they’d like explored, such as stakeholder dynamics or competitive pressure points.
Ask the team to provide warm intros, for recent wins for example, to encourage active participation in the program and to help get interviews scheduled.
Review research findings as a team and highlight what’s most useful for improving win rates.
Invite IcebergIQ to a sales meeting so the team can hear firsthand how the process works and how other sales teams benefit from it.
If you’re interested in accelerating and growing your sales through a win/loss program, please reach out to IcebergIQ here. We’d love to hear from you!