How win-loss analysis helps Revenue Teams increase win rates?

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How many times have you asked your sales team why they lost this deal? What if you get the superpower to be 100% sure about why the prospect didn’t really choose you? Win-loss analysis offers this power. It’s the process of systematically asking your buyer why he decided to accept your offer or not. Best B2B companies launch win-loss analysis at the end of each sales cycle because it’s the most trusted way to understand what really impacted the decision of their buyers. When they receive the feedback, they can adjust their tactics, get valuable insights on sales performance, competitors or pricing and increase their win rates.

Win-loss prevents you from speculating about why you win or lose deals

Successful revenue leaders systemize win-loss at the end of each deal. The basic first step is to ask your salespeople to fill in the CRM with the notorious “closed-lost reasons”. It’s a good base but not sufficient.

If you make sure to collect reliable feedback from your prospect once you win or lose a deal, you will be able to understand what exact drivers had a positive or negative influence on the final outcome. On a deal level, you know exactly why you lose this deal. On an aggregate level, you can make impactful conclusions as to where you lose money on your business. 

You get answers to wonderful questions such as : 

  • Why did my prospect decline my offer?
  • In the last quarter, why did I lose 7 deals to this particular competitor?
  • Why is one of my sales reps a low performer and how can I help?

Win-loss makes your sales team improve their performance

Launching relevant and targeted enablement program

Once you manage a successful win-loss analysis program, you start to understand : 

  • What are the decision drivers that have an impact on deal’s outcome
  • What are the decision drivers that helps you win
  • What are the decision drivers that makes you lose

We make sure our product, sales and marketing teams are aligned and that the company stays ahead of the competition. Understanding why we lose and why we win deals is now a must-have for us.

Head of Sales @Seiza

If you focus on the buying experience your prospect lives, you will get valuable insight on how your sales representatives can improve. More and more revenue leaders know that enabling their sales team is key. But best revenue leaders understand that before launching an enablement plan, they need to know where there are gaps and weaknesses. Some examples:

  • Is my demo customization perfect?
  • Is my sales team showing enough empathy and understanding?
  • Is the selling experience easy for our prospect?
  • Are my sales people showing expertise & knowledge?
  • Do we send the right sales content & resources?

Launching win-loss helps you target relevant coaching, improve sales tactics and boost team confidence. All of this results in a win-rate increase.

My concrete example

When I launched our first win-loss analysis program in my previous company in 2021, we were shocked by the results. Before this initiative, we relied on the “closed-lost” reasons in the CRM and we asked for a sales consulting agency to train our sales during 2 full days. When we had to choose on which topics, we selected generic topics such as discovery, closing, negotiation. 

At the same time, we started collecting feedback thanks to win-loss and in 3 months, we understand that : 

  • 5 big deals were lost because our sales didn’t show enough expertise. We didn’t lose because of our pricing or product features. We did lose because prospects didn’t feel confidence in our company to be experts in our domain. 
  • Our low performers were losing 15% of their deals due to lack of demo customization. Their prospects felt the product didn’t suit their needs.
  • Some deals (their sum was 130k annual recurring revenue) were lost because of lack of communications.

These 3 key points were not tackled in our training that we paid for. ROI was logically not there for the simple reason that we didn’t know why our team was losing deals. The issue was not our consulting agency, the issue was us.

Win-loss creates “win-back” opportunities

When you ask for a neutral third party like Diffly to make your win-loss analysis, you get valuable insights on why your buyer chose you or not. At the end of the interviews, we always ask if the buyer would like to stay in touch with you and in which timing. If the answer is yes, then you can re-launch the sales process with more intelligence and data that you didn’t have at the beginning. In the B2B world, you don’t always win the first time. You can win the third time. Win-loss helps you win more the second, third and fourth time.

Win-loss improve competitive win rates

Knowing its competitor is really important when you are in the B2B world. If you know like the back of your hand all of the following topics on your competitors, you get a competitive edge to win more:

  • Their strengths;
  • their weaknesses;
  • their ways of selling;
  • their pricing strategy;
  • the way they differentiate from you;
  • Etc.

You should find all of this information in battle cards that your ops, product marketers or sales enablement teams design for you. The thing is : it’s more than complicated to get battle cards up to date. Just because everyone learns and evolves. Win-loss analysis enables you to stay at the page and get a constant reliable view on your competitors.

Knowledge is power. 

Diffly's platform dashboard
Diffly's platform dashboard

Win-loss helps sales team influence product roadmap

Product roadmap is influenced by a lot of people

  • CSM people to improve customer retention
  • Product people 
  • Marketing people
  • Product marketers
  • Sales people

How can you make sure you make the right decision? Sales people can influence product roadmap thanks to data extracted from win-loss analysis. At Diffly, lots of our clients use qualitative transcripts to focus on what their buyer wants regarding their products & solutions.

Imagine you lose a big deal. Two different situations : 

  • Situation A :
    • You go to the product guys and say “we really have to fix this feature or to create this new feature so that I could win future delas”
    • Product guys will probably say “okay, we will review your point” 
  • Situation B :
    • You go to the product guys and say : “I just lost a big deal and I got this dashboard explaining why I lost it. I lost it for this particular main reason on this product we miss. You can find the transcripts from my prospect here. Can you add it to the product roadmap?”
    • Product guys will probably be more than okay to add it.

Win-loss duplicate winning strategies from top performers

If you have already been in a position to explain why you have top performers and low performers on the same floor, then win-loss analysis is here for you. By implementing a real analysis, you know the exact actions and reasons your top performers are doing. Same story for your low performers. 

You can launch a winning post-mortem with deals your top performers won. This will help your top performers make introspection and understand what they do to win. This will also help you to share to your low performers what is the recipe for success.

When is the best time to start a win-loss program?

Best Revenue leaders usually start win-loss when: 

  1. They want to become a leader in their market
  2. Win rate is not enough 
  3. They make decisions based on salespeople’ anecdotes 
  4. They want to reactive lost deals with intelligence 
  5. They have discrepancies in their sales teams  
  6. They need to ramp up quickly or to launch an sales enablement program


Top performers take time to analyze the reasons why they win or lose deals. They always want to receive constructive feedback on how to improve their selling experience. The best way to do it is to allow them receive reliable feedback through win-loss analysis. Even if they tried to ask their prospects why they didn't sign a contract, they will not receive full transparency. Here at Diffly, we are here to help your sales team perform thanks to the win-loss analysis automation platform. Feel free to contact me if you need more information!

Julien Cohen-Roussey
Co-founder & CEO of Diffly