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Why B2B Win Loss Analysis Is the Secret to Sales Success

As Albert Einstein famously said, “Insanity is doing the same thing over and over and expecting different results.”


Yet far too many B2B software and services companies keep plugging away with the same sales strategies without stopping to dig into why they’ve won or lost a deal.

Don’t make the same mistake. Following a simple, straightforward process known as a win-loss analysis to hone in on what’s working and what isn’t won’t just streamline your efforts—it’s the surest way to meet your sales goals. That’s why it’s an essential part of our B2B sales training.


What Is a Win-Loss Analysis?

B2B win-loss analysis is the process of evaluating every deal your team has proposed to a potential customer to understand why it was won or lost. It involves looking at variables like company size, deal type, industry specifics, lead source, and more to hone in on the types of clients who are more likely to convert.


A win-loss analysis is one of the first steps of the SaleLeap outbound sales training process because it provides a critical baseline of information about what’s working and what isn’t in your company’s sales efforts. Once you’ve identified patterns in the sales that convert and those that don’t, you can narrow down your Ideal Customer Profile (ICP) and more effectively target prospects who are most likely to deliver significant value. 

Despite its effectiveness, many companies haven’t gone through this exercise before. While it may seem daunting at first, once you’ve developed a clear process for win-loss analysis, it becomes a streamlined and eye-opening exercise. We recommend that our clients conduct win-loss analyses quarterly as part of their sales process development, with once a year as a bare minimum.

Win Loss Analysis Quarterly Review Infographic

How to Conduct a B2B Win-Loss Analysis

The win-loss analysis process that we teach as part of our B2B sales training can be broken into four simple steps: plan, hypothesize, run reports, and review your findings. Follow the steps below, and soon you’ll be on track to streamline your B2B outbound sales strategy and operations, find new efficiencies, and land more customers than ever before.


1. Plan Your Win-Loss Analysis

First things first—before you start pulling data, you need to make a plan. At this point, it’s important to ask a few key questions:

  • Who should be involved in the analysis?
  • Who will lead the analysis process and present findings to the team?
  • What systems will you use to extract and analyze data?
  • What is your timeline for completing the analysis?


While you’ll want to talk to every member of the sales team to get data and it’s essential to include everyone in the discussion of your findings, you don’t want too many cooks in the kitchen at the early stage. Identifying a point person to lead the effort, as well as milestones and deadlines, is the best way to ensure that the analysis moves forward. Once the win-loss analysis becomes an SOP (standard operating procedure) for your team, integrating it into your quarterly reviews will become second nature.


2. Make Hypotheses

In all likelihood, you have a lot of data about your customers—and you don’t want to make the mistake of chasing the numbers in too many different directions. Identifying hypotheses to investigate will help guide your analysis and ensure you don’t get bogged down in the sheer number of factors that could potentially impact sales. Instead, testing out your theories will help guide you toward actionable insights.


This is the time to brainstorm with team members. Develop a minimum of five hypotheses you would like to test during the win-loss analysis. The aim is to narrow down characteristics of your target market that correlate to increased deal closing. You can also look at the sales process itself to better hone your process for approaching new leads.


Some examples of potential hypotheses to test include:

  • Companies with under $1M in revenue take longer to convert
  • Companies with less than 10 locations are more likely to convert and are more successful customers
  • The sales process moves faster when we talk to the CTO first
  • When the use-case was X, we closed at a higher rate


Ultimately, you’re looking for the common attributes that will lead to the following outcomes:

  • High conversion rates
  • Fastest speed through the funnel, from lead to deal closing
  • Highest revenue
  • Partnerships that fit your product (e.g., don’t lead to scope creep)


Some of these hypotheses will likely prove to have an impact, while others won’t turn out to be true according to the data. That’s great—it’s exactly why we test these ideas rather than making decisions based on assumptions.


3. Run the Report

Once you have the hypotheses you want to test in place, it’s time to dive into the data. Start with whatever CRM system you use, and extract data covering the time period you’re looking at (which should be at least a year for valid results). Keep as many variables in as possible at this point, so that you can slice and dice by different factors. This is also a great time to talk to sales reps to fill in any gaps and add any additional notes that didn’t make it into your CRM. Don’t be scared if you end up with a sheet with lots of columns—the more information you have, the more actionable your conclusions will be.


Start with your overall numbers—conversion rate, speed through the funnel, revenue, customer success rate, etc.—so that you have baselines for comparison. Key figures to look at include your win/loss ratio and your win rate.


Your win/loss ratio compares the number of deals you’ve won to those you’ve lost. To calculate it, simply divide the number of opportunities you’ve won by the number you’ve lost.

Your win rate reveals what percentage of your sales activity leads to a closed deal. To calculate your win rate, divide your number of won opportunities by the total number of won, lost, and in-progress opportunities in your records.


Once you have those figures, you can pull out the variables from your hypothesis. Do companies with more locations have a better, or worse win/loss rate than average? Does win rate increase if you start with a C-level contact? Of course, you’ll also want to parse the data by numbers like total revenue (compared to average) and speed to a deal. 


During this stage, you should start to see a number of high-performing market segments emerge. For example, you might find that companies with operations above a certain size are a good fit, or that companies serving a specific type of customer better align with your processes. Look for the little details that give insights into why you’ve won or lost deals. 


Typically, you want to hone in on the customers with the highest lifetime profit. Don’t just look at revenues, since higher gross revenues often come with increased cost (and time to convert). Really crunch the numbers on the cost of customer acquisition. This data will help you identify where to focus your efforts in the future. Of course, you’ll also want to think about factors like market size and growth projections, and remember that sometimes getting in on the ground floor with a company can pay off big in the long term.


4. Review Your Findings

Now that you’ve validated your hypotheses and come to some initial conclusions about where to focus your outbound sales for SaaS or B2B products, it’s time for the whole team to regroup.


The person who led the analysis should present the win-loss findings to the whole team, being sure to offer plenty of time to ask questions and discuss. In fact, it can be helpful to have the initial presentation, share findings with the full group, and then reconvene to brainstorm how to use that data moving forward. You may find that certain angles weren’t considered initially, or that the data reveals a pattern you hadn’t noticed at first—that’s normal and to be expected. Stay open to those surprising findings, and rerun the data to look into any new hypotheses that emerge.


Now comes the fun part—using what you’ve learned to bump up your sales! As a team, use the data to refine your Ideal Customer Profile and decide which data findings you’ll act on and how. Be sure that everyone working on lead sourcing understands the new ICP and how to look for leads that fit the profile. Your copywriter can tailor a personalized message in emails to fit the new ICP. Sales reps and account executives should also feel solid on this methodology since it will help inform how they talk to prospects.

Win Loss Analysis Process Infographic


Running a win-loss analysis might seem like a lot of work—but we promise, a small upfront investment in time and energy will pay massive dividends. When you’ve identified what’s working and what isn’t and built a narrowly targeted, effective ICP, you’ll save immense amounts of time chasing leads that won’t go anywhere or won’t offer much in the way of profit. The win-loss analysis is central to our B2B sales training approach for a very good reason—it works. Try it yourself, and watch your conversions, and profits, soar. 


Looking for more help developing your win-loss analysis and ideal customer profile? SalesLeap offers outbound sales training for B2B companies ready to accelerate their growth. Reach out to learn more about how we can help.. Book a discovery meeting today. 



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