Product Marketing
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November 29, 2021

A Step-by-step Guide to Win/Loss Analysis

By Aggelos Mouzakitis

Why do you win some deals while you lose others? What is your winning persona and how often do you lose against the (x) Competitor? How do customers make decisions and what can you do to affect them?


Win/loss analysis insights have proven to be a very efficient tool not just for salespeople, but for every company team that seeks to better understand their competitive landscape and optimize their processes. 

Let me walk you through the steps of a successful win/loss analysis that will provide you solid insights about why you win, why you lose and what improvements can you make.

We will take a close look at how to extract valuable insights from your sales reps’ notes and recordings but also how to conduct customer interviews to identify reasons for winning or losing.

What is a win/loss analysis & how will it impact your teams’ performance?


A win-loss analysis is the process of identifying exactly why a client bought your product—or why they didn’t. 

More specifically it’s the process of evaluating performance related to a couple of variants such as competition, industry, persona, lead source e.t.c. By analysing all the above, you get accurate data that reveal why some deals are won and others lost. 

When identifying the buyers’ decision drivers, there is a clear understanding of what you can improve and what you already do well. Keep in mind that it’s not only a winning analysis. It’s a win/loss one! Loses will bring you as valuable insights and improvement points, as wins!

With these insights in your hands, your teams will begin to sell more but also enter a constant self-improvement loop.

There are 4 main steps to execute a win/loss analysis.

Let’s take a closer look at how you will successfully go through all these steps to upgrade your team’s sales performance. 

Step 1: What is a win/loss ratio and how to calculate it

Before focusing on improvements, it’s important to begin with measuring your current performance. To do so, you need to calculate your win rate and your win/loss ratio. 

Let me explain: 

Win rate is the number that shows how many of your potential deals within your sales activity turn into paying customers. 

It can be calculated just by dividing the won opportunities by the total customer opportunities that came up. Keep in mind that open cases do not count on the total opportunities number.

Win/loss ratio, on the other hand, measures the wins over the losses. In other words, how many times you win and how many times you lose in a given amount of time. 

In order to come up with the win/loss ratio number, you just have to divide the number of the cases you won, by the number of the cases you lost.

Long-term, you will use these data as a point of reference to measure your improvements. 

Step 2: How to collect meaningful data to identify why you win and why you lose

There are many sources you can take into consideration when it comes to win/loss data collection. The more different sources you include in your analysis, the wider the view you will get.

We will take a look at how to leverage sales notes and recordings but also how to conduct customer interviews and measure marketing data. 

  1. Sales Data (notes + recordings)

Help your teams perform better and let them take you way ahead in the sales game, by taking a closer look at their notes and recordings.

You have two options here. 

First, you can take a tour through your sales reps’ CRM notes and find many useful data about user cases, pain points, competitors, or even customer objections and arguments. 

Yet, if you really want to get to the core of why you win or why you lose, you could analyse your sales recordings. You can begin with a minimum of 12 videos and try to mark down the common patterns of won cases and the causes of the lost ones. 

Here are some investigation points you can keep in mind while analysing the recordings: 

-What is your winning/ losing customer persona 

-Over which competitors you win and over which you lose 

-Which are your winning/ losing lead sources

By grouping your observations you will soon find out that there are patterns that occur again and again. Some of them bring on wins and some lead to losses. 

Gather these valuable learnings from sales’ notes and recordings and get closer to uplifting your teams’ performance.

2. Customer feedback interviews

Sales reps notes are valuable but if you can directly talk with the customer you won or lost, then you are even closer to understanding why they did (or didn’t) choose you. 

The best way to learn how potential customers perceive your selling process from beginning to end, is by interviewing them.

Interviews with customers bring on extremely valuable insights as you practically speak directly to the actual decision-makers. You need to decide whether these interviews will be conducted by a third party or by an in-house interviewer. 

It’s considered a best practice to hire a third-party interviewer as they will ensure that there will be a neutral interview environment and the conversation will be safely guided into bringing up real useful information. 

A well-trained professional interviewer will create the right atmosphere, ask the right questions and retain the important information. Plus, they will deliver the insights in an easy-to-get format. Another benefit is that if the interview goes off-script, they will be able to handle it and go with the flow. 

If you are not ready to hire an outside vendor, consider delegating interviews to members of your marketing team. There are more chances that they will not take any comments about the product, or sales process personally and will be able to extract important information from interviewees.

Here are some useful tips on how to conduct a customer interview, in case you decide to run one without a third party expert:


3. Marketing Data

When it comes to fully understand why deals are won or lost, it’s quite useful to also take into consideration trends across the interactions between your marketing content and your prospect customers. 

Leverage your marketing automation tools and your CMS to segment user opportunities by buyer profile, age, traffic source, lead source, engagement e.t.c. 

Use all the means you have and remember to not only focus on lost prospects who walked away, but also on won customers who chose your product. There are many valuable learnings concerning the things you already do well. 

Step 3: What to look for, when analyzing your insights

After gathering all data from sales recordings and notes, customer interviews as well as marketing channels, you need to specifically define what you need to know about your won and lost cases, in order to translate your insights into clear learnings

Keep in mind that you need to identify common patterns in both wins and losses, strengths and weaknesses. So, carefully take into consideration all sides of qualitative feedback.

Here are some basic points you should look for: 

Also, you can keep a couple of important customer sayings and insert them in your communication and sales efforts to increase empathy. 

Combine all these findings into an easy-to-read format. The more clear and visualised you present the data, the more aligned your next action steps will be. 

Step 4. Share the learnings with your teams and drive action

At this point, you should already have a clear understanding of why you win some deals while you lose others. 

Yet gathering insights for the sake of insights is never the goal. It’s time to translate your findings into actionable steps that will help your sales reps improve their performance.

Sharing your analysis in a way that all your team can use, will be helpful in drawing a more efficient win strategy. 

Visualising data is the first step in helping your team understand their strengths and pain points and set concrete actions to be put in motion. The whole point is to create a scalable process that will help your sales reps bring on more wins and keep learning from their losses. 

Yet, findings and learnings from the win/loss analysis can also be quite useful across departments. Don’t hesitate to share the results with your marketing team, product managers, client service or even engineers. It will help all teams to better understand customer buying behaviour and acquire a pint of empathy into what they do.

Achieving sales targets and goals is challenging.

Providing clarity for wins and losses is the first step to helping your team

optimise their sales. But there is more to that. By analysing your sales cases, you will build a sustainable feedback loop that makes your team self-improving.

With actionable insights on your hands, you are able to win more, but also transform your team into:

A solid basis you can rely on to drive action, multiply your sales and achieve your goals.

Keep in mind that companies who listen to what customers have to say are the ones who develop more reliable relationships with customers in the long term.

So, if you haven’t conducted a win/loss analysis yet, it’s about time to start!

Aggelos Mouzakitis

Aggelos is the founder and Growth Product Manager of Growth Sandwich. He is among the first Customer-led experts in the world, leveraging advanced, Jobs-to-be-done customer research to orchestrate and guide Growth for B2B SaaS companies. A- and B- series SaaS are hiring him to organise, design and execute programs that infuse the whole company with qualitative data, empathy and the necessary knowledge to address any growth dilemma. In the last 4 years, he has worked with more than 100 SaaS companies and trained literally, thousands through my physical and online courses.