30 signals that you need to implement Win-Loss Analysis

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According to Gartner, B2B companies that take a more comprehensive win-loss analysis approach have seen a 15% to 30% increase in revenue and up to 50% improvement in win rates. This is huge but how can you be sure win-loss will have a real impact? In this article, I share 30 signals that will help you to understand if you have or not to implement such a process across your company. I classified these signals by thematics (general signals, signals for product marketing manager, revenue leaders, product leader, marketing leaders and CSM leaders).

Win-loss analysis is a new superpower to understand what really drives your buyer’s final choices 

Once a deal is lost or won, launching win-loss analysis helps you understand what are the exact reasons that positively or negatively impacted your buyers’ final decision. This process helps you step into your buyer’s mind. If you successfully perform win-loss, you become close to your buyer’s needs and you get better performance. According to Accenture, companies that perform continuous win-loss analysis increase their win rates by 18%.

visual graph explaining that Diffly’s platform allows B2B companies understand why some clients have churned
Decisio drivers graph

12 general signals that you need to implement win-loss

  1. You want to be best-in-class and become a leader in your market
  2. You are not satisfied with your current win rate and/or your win rate is decreasing
  3. You don’t really understand what makes you lose and makes you win
  4. You need to align sales, marketing and product with one single source of truth
  5. You lack direction for your strategy and want to be data-driven and not feeling-driven
  6. You make decisions based on salespeople’ anecdotes 
  7. You ask your sales representative to fill your CRM’s drop-down list of win-loss reasons at the end of each deal
  8. You want to leverage more your previous lost deals and reactive them with intelligence
  9. Your way of selling is evolving from a transactional model to a mid-market / enterprise model
  10. You launch a new pricing model
  11. You want to identify new trends on your market and / or new levers of growth
  12. You have some insights on what makes your buyer take their decision but ignore their weights

3 specific signals for Product Marketing Manager
(in addition to the general signals above)

  1. You lack reliable insights to launch and maintain an efficient GTM strategy
  2. You start to lose against one competitor or you have a low win rate against a particular competitor
  3. You have competitors you don’t know well and you struggle building efficient battle cards

6 specific signals for Revenue leaders
(in addition to the general signals above)

  1. You have big gaps in sales rep’s performance  
  2. You have a sales representative with low win rate
  3. You need your sales team to ramp up and you want to build an efficient sales enablement program
  4. You enter into a new geographic territory or a new market
  5. You want to focus on a new ICPs or buyer personae
  6. You are not sure about how your top performers actually perform

3 specific signals for Product leaders
(in addition to the general signals above)

  1. You are not 100% sure that your product roadmap is aligned with your buyer’s needs
  2. You have launched a new feature / product and you need to understand how the market is reacting
  3. You struggle to prioritize your product roadmap

4 specific signals for Marketing leaders
(in addition to the general signals above)

  1. The pipe generated by your marketing actions doesn’t convert well
  2. You don’t know how your company is viewed externally
  3. You just launched a new marketing & positioning strategy
  4. You don’t have enough insight on what drives your leads to become clients

2 specific signals for CSM leaders
(in addition to the general signals above)

  1. You have an important churn rate and your customer experience is not satisfying
  2. You want to leverage your client base to close upsell and cross sell opportunities

Win-Loss Analysis is usually owned by Product Marketing Manager teams and / or Revenue teams (particularly Chief Revenue Officer, VP Sales, Head of Sales, all sales representatives and Revenue Operations, Head of Ops). 

Executives (CEO, CSO), marketing professionals, product teams (VP Product, Product manager), customer success managers and competitive analysts are also looking to master their jobs thanks to win-loss. 


If you feel personally involved in some of these signals, then you are in the right place and you probably need to launch a win-loss analysis program. At Diffly, we are experts on this topic and we help B2B companies launch their win-loss program from A to Z. Feel free to contact us or subscribe to our newsletter to receive more information on win-loss, revenue enablement and competitive intelligence topics.

Julien Cohen-Roussey
Co-founder & CEO of Diffly