Sales Win-Loss Analysis: Lessons From the Trenches

Sales Win-Loss Analysis: Lessons From the Trenches

Jordan Weaver
Jordan Weaver
7-minute read

Unlock the potential of your sales teams with sales win-loss analysis. Outsmart your competitors, increase win rates, and make data-driven sales decisions.

Table of Contents:

  1. My Experience: Sales Win-Loss Analysis
  2. What is Sales Win-Loss Analysis
  3. What is B2B Win-Loss Analysis
  4. Advantages of Sales Win-Loss Programs
  5. Outcomes of a Win-Loss Analysis Strategy
  6. Sales Win-Loss Data: Build Your Foundation

My Experience: Sales Win-Loss Analysis

While I've never worked for a company that had a robust program for sales win-loss analysis, I know for certain that if those companies did, I would have sold more deals, generated more leads, exceeded my KPIs, and my managers would have known exactly where to improve my sales behavior. Sales win-loss analysis can provide priceless knowledge for salespeople.

Some of my sales history

At the time of writing this article, I've been in sales for a little over 7 years now, mostly in the B2B SaaS industry. I've worked with some amazing salespeople and sales teams, and I've worked with some pretty bad ones. Notably, the experience I had with my team at Fleetmatics during the acquisition by Verizon Connect (Verizon Telematics at the time) in 2016 is what provided a rock-solid foundation for my sales career. I'm forever grateful for that experience and for those people who supported me there.

Those that know about Fleetmatics usually know them for one main reason, which is their amazing sales processes for their time. While I'm not a 20-year seasoned sales veteran and still have a ton to learn about sales, I've worked with quite a few different sales processes and systems up to this point. With that said I'll put my point simply, which is that I've yet to work for a company that has a robust win-loss analysis program. And usually, they don't even have a basic sales win-loss analysis program other than CRM reason codes. When making business decisions, this type of research is critical for having supportive data instead of just wildly guessing what to do next.

So what's my point?

This is no bash on any of the previous companies I've worked for. In fact, it's no surprise. Why is it no surprise? Well traditionally, win-loss analysis has been primarily known as sales win-loss analysis, which solely supports sales teams. Over time, many tools and methods have come to market to solely support salespeople that are sometimes more cost-effective than sales win-loss analysis (depending on the business objectives). The reality is that not many companies, including very large enterprise businesses, understand how to build a win-loss program to drive action and impact their business in multiple ways other than just sales. It's not easy, but more than anything there are hundreds of different ways to do it, and some of those ways are much more valuable than others. This has to do with the nature of win-loss analysis which is that in order for it to be highly effective, it must be designed in a way that is completely custom and bespoke to a business.

I think the demand for win-loss analysis is increasing rapidly in this recessionary environment, as more and more businesses and stakeholders are starting to catch on to the true value of win-loss when it comes to supporting not only their sales efforts but also their marketing and product management efforts. This research can really help you become one of the businesses that thrive in a recession.

As the picture becomes more clear for businesses to know what to look for in a valuable win-loss analysis program, more and more businesses will start to ask themselves how they should start their own win-loss analysis program. Hopefully, this article will help those people who are new to or are rediscovering win-loss analysis.

Sales win-loss analysis vs win-loss analysis

So, where to start? Usually, you'll want to start with a 'sales win-loss analysis' program. The difference between this and a fully robust 'win-loss analysis' program is that most of the data and insights extracted from this sales program will be dedicated purely to helping sales. The data might not make its way outside the account team yet, but if this is done correctly, it will lay the foundation for a robust program in the future that can extend to other departments.

A full win-loss analysis program includes ways to synthesize your sales data into actionable recommendations that impact marketing, product management, RevOps, and even improve your internal customer retention programs or optimize your customer experience in general. These full programs are much harder to build out, and if you currently don't have some type of scorecard for keeping track of your sales data in a more robust way, it'll be hard to make progress. Starting with sales is much more simple, and will drive better data extraction when the time comes for a full win-loss analysis program.

What is Sales Win-Loss Analysis

Sales Win-Loss Analysis is a systematic approach to organizing sales win-loss data in a way that provides visibility into trends, patterns, and insights over time. This strategy will ultimately lead to supporting sales, marketing, and product management at a minimum. This is the foundation of win-loss analysis.

Many companies running their win-loss programs internally face a huge problem. They run a post-mortem, basic analysis of an opportunity alongside their CRM’s reason codes. A handful of people in sales might learn from the findings, and when the analysis is finished, all of the data is lost. None of the data is making its way outside the account team, and there isn’t a scorecard keeping track of what’s happening over time.

No trends, patterns, or insights can be extracted from this, let alone actionable recommendations that drive impact to multiple departments. Having a solid system of data storage for sales win-loss data is the only way to ensure data can be distributed properly, and in most cases, for a company to see a large ROI from their win-loss initiatives.

What is B2B Win-Loss Analysis

A full B2B win-loss analysis program is a valuable research methodology for businesses to understand their successes and failures throughout sales, marketing, and product pipeline. Many companies choose to leverage a partner like Anthroware to gain an objective third-party perspective on their sales process, win-loss ratio, go-to-market strategy, product-market fit, and to inform the product pipeline.

Importance for B2B Companies

In the ever-growing B2B market, it is essential for companies to have a thorough understanding of what drives wins and losses. This helps them stay ahead of their competition and have a true understanding of their total addressable market and ideal client profiles that generate the most demand and revenue. Win-loss data shouldn't just support sales, it should support multiple departments.


Here we aim to explore the importance of comprehensive record-keeping or data storage practices from sales wins and losses, and the impact this data has on a B2B company's sales, marketing, and product pipeline efforts. To put it simply as you can see in the image below, this article will focus on the Catalyst and the Research sections of win-loss, whereas a full W/L analysis program would focus on all 4 steps.

Sales win-loss analysis
Sales Win-Loss Analysis

Advantages of Sales Win-Loss Programs

Sales win-loss can support much more than just B2B competitive intel initiatives. By providing a deeper understanding of the actual customers within a market, qualitative insights are extracted that include the true feelings of the customers within specific market segments as they go through the sales process for specific products or services.

Improved Accuracy in Sales Forecasting

Anthroware has found that companies conducting this B2B win-loss research have a more accurate understanding of their sales pipeline, allowing for better forecasting and more effective resource allocation.

More Effective Sales Process

Most companies that conduct win-loss are better equipped to identify the strengths and weaknesses in their sales process, leading to improved win rates and a more efficient sales process overall.

Insights Into Customer Behavior and Preferences

Win-loss allows companies to better understand their target audience and tailor their sales and marketing efforts accordingly. They can also identify and capitalize on emerging market trends and shifting customer preferences. This will help develop internal customer retention strategies.

Support for Product Marketing

Win-loss programs provide data-driven decisions for growth and success. For example, it can reveal the key differentiators that customers are looking for in a product, allowing the marketing team to highlight these features in their messaging. Creating a workflow to drive data to product marketing from your sales win-loss analysis is one of the easiest ways to start impacting other departments due to how closely tied sales and marketing are.

For example, your sales analysis can also identify gaps in their total addressable market, providing insight into areas where the company can differentiate itself and better meet customer needs.

Informing the Product Pipeline

A full B2B win-loss analysis is not just a way to evaluate sales and marketing efforts, but it can also inform the product pipeline. By looking at what factors led to wins or losses in sales, companies can identify areas for improvement in their products or help you understand how to choose your ideal software development partner.

For example, if a competitor's product is chosen over the company's product because it has a feature that the company's product does not have, the company can prioritize adding that feature in its next product update.

Another example is if the company is consistently losing deals due to longer implementation times, the company can work on streamlining the implementation process to make it more efficient. By informing the product pipeline, companies can stay ahead of the competition and better meet the needs of their target customers.

Informing the product pipeline with win-loss analysis is a deep subject and it's worth saving for another article by itself. Let's just keep it simple and realize that the more work that's put into developing your sales win-loss analysis program, the easier it will be in the future to begin informing the product team when you get to that step. Don't slack on building a process of data extraction and data synthesis! It's debatably the most important part and the main purpose of this article.

Outcomes of a Win-Loss Analysis Strategy

It is essential that your B2B company receives these 3 outcomes from your sales win-loss analysis strategy. A win-loss program cannot be conducted without first having a strategy of organization for your win-loss data and insights. This can all be put in place similarly to having a strong requirements-gathering process in a development process

Support Sales, Marketing, and Product Pipeline Efforts

  • Record-keeping for your sales data provides valuable insights into customer behavior and purchasing habits for visibility into trends and patterns over time.
  • This information can ultimately be used to inform sales, marketing, and product pipeline efforts, enabling companies to make data-driven decisions.
  • For example, by regularly reviewing and keeping track of win-loss data, companies can ensure their data makes its way outside of the account team and into other departments such as marketing and product, and provides visibility into how those trends relatively change over time.

Develop a Powerful B2B Win-Loss Analysis Program

  • In a highly competitive B2B market, it's essential to stay ahead of the competition by continuously improving and adapting to changes in customer behavior, which can only be done by interpreting a dataset that’s been built over time.
  • By keeping thorough records of competitive information, companies can identify patterns and trends in customer behavior relative to their competitors and use that information to better understand how to take action and inform their business-level strategy.
  • Over time this helps with continually refining sales messaging, addressing any shortcomings in marketing strategies, and improving product offerings.

Retain customers and attract new ones

  • Helps companies to understand what factors lead to customer retention and acquisition.
  • By identifying the reasons behind customer wins and losses, companies can make informed decisions that lead to increased customer satisfaction and loyalty.
  • This, in turn, leads to increased customer retention and improved customer acquisition efforts. Again, only possible with a large dataset that continues to grow over time through solid record-keeping.
  • If the main business objective for stakeholders is to have an increased focus on churn, customer retention, customer lifetime value, net revenue retention, etc., a win-loss analysis program might not actually be the best fit. When working more directly with customer success teams or customer experience teams, we usually suggest Customer Retention Programs to support their direct initiatives outside of sales and marketing.

Sales Win-Loss Data: Build Your Foundation

It's becoming increasingly clear that these practices can play a crucial role in the success and growth of a B2B competitive intelligence program for a company. From informing sales, marketing, and product pipeline efforts to retaining customers and attracting new ones, a sales win-loss strategy provides a foundation for full win-loss programs, customer behavior analysis, and understanding purchasing habits.

It's our belief that B2B companies should take advantage of the benefits of sales win-loss analysis for keeping a detailed scorecard of their sales data and developing a robust system as we continue through economic uncertainty. Comprehensive sales programs and practices will ensure that companies have the information and insights they need to make informed decisions that drive growth and success, ensure their data can ultimately make its way outside the sales account teams, and provide visibility into how trends change over time to support other departments.

We hope this article has been informative. Whether you're just starting out or you're an established player, these practices are essential for success and growth. So, take our call to action and start conducting regular sales win-loss analyses and implementing comprehensive sales practices in your company today. Once your sales are optimized, you might even be in need of a digital transformation consulting firm to take the next bigger step of transforming your company!

Let's get started!

Find our contact page from our navigation bar to get in touch with Anthroware and receive help in developing your own robust B2B win-loss analysis strategy or to learn more about our more simple programs such as sales win-loss analysis.

Jordan Weaver
Jordan Weaver
Enterprise Account Executive & Strategic Partnerships
Atlanta, GA

Win-Loss/Churn Analysis | GTM-Strategy | Sales Enablement | We deliver actionable recommendations, not a PDF that sits on a shelf.