How to Conduct a Win-Loss Analysis to Improve B2B Sales

Let’s face it, you can’t win them all. This is a lesson we are forced to learn at an early age. Whether losing a board game to your older sister, a fantasy football game to your best friend or putt-putt vs your significant other, at some point we all come to terms with the fact that victory all the time is impossible.

I know it, you know it, and Sales VPs certainly know it. What matters is that we learn from our losses and apply these lessons to future opportunities. This is why the win-loss analysis is a critical aspect of the sales process.

Why should you conduct a Win- Loss Analysis?

There are many benefits to win-loss analysis, including:

  • Improve efficiency and resource allocation
  • Increase win rates
  • Identify weaknesses in your sales process
  • Capture competitive intelligence
  • Drive product innovation and address feature gaps

Tracking your win-loss ratios and understanding them are two different things. How you interpret the activities leading up to the end of a deal – both positive and negative—will help determine better ways to leverage trends and pivot to avoid future losses.

But how should you conduct this analysis? What should you be looking for? And where should you be searching?

How to Segment a Win-Loss Analysis

A win-loss analysis can be conducted from a variety of different angles, depending on what you’re looking to achieve. Traditionally, these have been manual processes, so revenue teams have been forced to choose a key field by which to segment, such as Lost Reasons, Employee, Lead Sources, etc.

However with advanced analytics, it’s now possible to get much, much deeper. We’re talking about the ability to identify the exact inflection points within your sales cycles where deal trajectory changed, based on a variety of factors.

One you understand that milestone, you can use it to improve your value proposition, apply feedback in rep 1:1s and coaching sessions, and incorporate it into day-to-day activities.

Building Win-Loss Dashboards

With more than 350 out-of-the-box RevOps dashboards and reports, it should come as no surprise that InsightSquared provides a variety of ways to look at win-loss analysis. These reports are self-serve and can be launched in minutes, providing clear views into the state of your pipeline and the secrets behind your wins and losses.

What are some best practices in conducting a win-loss analysis?

  • Look Beyond a single Quarter: Most CROs want to look at relatively long periods to discover actionable trends, while taking into account outliers such as new product launches, changing market dynamics, competitive changes or even a global pandemic. All of these factors may significantly affect your sales cycle. So, it’s essential to invest time in understanding metrics and how your ability to win or lose business changes over time.
  • Explore the Dimensions of the Sales Cycle: Having the ability to dissect your pipeline activity through different categories can give you a 360 view into the health of your pipeline. Explore data based on region, industry, and sales reps or managers. Ask: What are the key indicators that drive success so that you can drill down and start creating repeatability? And how do you take these things that you learned during your win-loss analysis and apply them into your weekly or monthly management cadence?
  • Cohort your analysis like you segment your goals and business: Every metric can be tuned to the specific data that your business cares about and drives your business. How do you segment your business? If I don’t want to track data by region and segment by industry, you can save those parameters as a template and continue editing that. Furthermore, you can also track how your pipeline is being created by region and how that tracks against pipeline creation goals.It matters how you achieve your goals. If you’re underachieving in a particular region and overachieving in another, you can make necessary adjustments. The goal is to analyze the underlying inputs that contribute to achieving revenue targets.

What should be in a Win-Loss Dashboard?

  • KPI Trends: A KPI trends dashboard is a tool and a template designed to track secondary amount fields, like the revenue split between license and non-recurring revenue, as well as several different ways that you need to look at your business over time.
  • Pipeline History: When assessing wins and losses, you want to be able to look at a pipeline history by stage over time. This gives you insight into key questions such as — Has my open pipeline increased or decreased over time? Have my number of deals increased or decreased over time? How have those deals been forecasted, and how has that split adjusted and evolved over that time? What you’re looking for is the overall health of the business. If your pipeline is trending up to the right, ask what’s the source of that net new pipeline. If your pipeline is trending down and to the right, why are you losing more now? If your pipeline is turning up to the right, look at how your pipeline creation is trending, and figure out what’s driving that.
  • Funnel Stage Conversion: Look at win rates over time to see how you’re actively converting through the sales stages. Is your team, or a particular rep, struggling in specific stages of the sales cycle? You want a dashboard that provides clear visualization as well as the ability to drill into the space and help determine how those conversion rates or win rates changed based on the deal size. We also offer dashboards that can help companies understand why win rates decline and provide accompanying data that can help to get back to historical averages. Clients can even take advantage of InsightSquared’s robust library covering sales cycles analysis, sales price analysis, win rates, and much more.

Using InsightSquared to conduct a win-loss analysis

InsightSquared offers robust analytics that help your team understand exactly why you are losing deals at both a macro and a micro level. The result is our customers get ahead of issues before they repeat themselves.

Consider Charlotte, an experienced CRO. She has two direct first-line managers who have reps that report to them. With InsightSquared, she can manage KPI trends, not just holistically for the business but also by team. As a top-level business level analytic, she’ll be able to see these metrics by person, as well. Our dashboards can also filter down to particular fields. Within the platform, every field is filterable—derived fields, date fields, amount fields, industry fields. It’s the information you need, how you need it. For example, if Charlotte wants to understand her win rates in high-tech only, that’s possible.

InsightSquared offers dashboards for that win-loss analysis, including high-level profiles of your baseline, information on deals that look good, and data on deals that were lost. Every 1-2 weeks, you’re going to look at a report and examine the timeline of the deal’s progression, including detailed information about activities that occurred six weeks before the end of the deal. This information paints a clear picture of what happened.

Once you set those parameters for specific opportunities, you can look at the pattern of engagement, including when a deal went dark. You may discover that the sales rep wasn’t effectively working in it, and information didn’t get documented in your pipeline review process. That presents an opportunity to tighten up processes to identify future loss deals as soon as possible. So, viewing the last six weeks of a deal is an excellent foundation for coaching sales reps and reviewing the causes of wins and losses regularly.

Conducting a win/loss analysis by lead source is just one of the many ways in which CROs and RevOps teams can study their victories and defeats. The lessons gleaned in these analyses should then be applied in future decisions.

Interested in seeing a sample win-loss dashboards and learning how easy it is to configure for your team? Request a demo with our sales analytics experts.