Types of Data Needed for a Successful Win/Loss Analysis

A win/loss analysis is one of the most critical analyses that a product marketer can create to benefit their teams. Conducting interviews and collecting data can help your entire organization improve customer acquisition and retention strategies and grow the business. All of your teams will benefit from the win/loss analysis you produce. Though there is no single way to conduct a win/loss analysis, there are many helpful pieces of data that can contribute to your results. It’s essential to incorporate both quantitative data and qualitative data into your analysis. Let’s dive into the best practices for conducting a successful win/loss analysis.

Quantitative Data

Quantitative win/loss analyses allow you to put hard numbers to your team’s successes and opportunities. There are a handful of quantitative data points you should be calculating to gather the most accurate information across your organization. Calculating different win rates can highlight how well you’re doing and where you need to invest more resources. Here are the key data points to form your quantitative analysis. 

  • Overall Win Rate
    Your win rate is a measure of the percentage of sales opportunities your team successfully turns into a paying customer or client. To calculate your win rate, take your # of won opportunities/# of total opportunities. When calculating your overall win rate, you should be sure to calculate it both for overall opportunities, and again while excluding open and in progress opportunities that may still close in the future.

  • Win/Loss Ratio
    A win/loss ratio compares your won opportunities against your lost opportunities to put wins and losses side-by-side. To calculate your win/loss ratio: # of won opportunities / # of lost opportunities.

  • Competitive Win Rate
    Competitive win rates shine a spotlight on your success rate in opportunities where you go head-to-head with another solution. When calculating your competitive win rate, you can group all of your competitive deals together for an overall rate, as well as calculate this by each individual competitor. You could also group your competitors into tiers and calculate your win rate by direct, indirect, and aspirational competitive deals. This formula is the same as your overall win rate, but only include data from specific competitive deals. To calculate your competitive win rate, follow the standard win rate formula, but take the # of opportunities won where you were head-to-head with a competitor / # of total opportunities where you went head-to-head with a competitor.

  • Win Rate by Sales Segment
    Calculating your win rate by sales segment is important so that you can see how each of your sales teams is doing. For example, if you have one enterprise sales team and one mid-market sales team, you can calculate your win rate for both so that you can see which team has higher success, and which needs work on closing more deals. To calculate your win rate by sales segment, follow the standard win rate formula, but take your # of opportunities won in the segment / # of total opportunities in that same segment.
     
  • Win Rate by Product
    If your company sells more than one product and has specific sales teams or reps dedicated to selling that product, you should calculate those specific win rates. This will help you understand which products are selling more effectively, and conversely, which deals aren’t closing. This will allow you to allocate more sales enablement resources to help your team sell underselling products. As well, if you dig a little deeper and figure out your loss reasons per product, you can provide that feedback to your product team to help them improve the product and better serve the needs of your market. To calculate your win rate by product, take your # of won opportunities per one product / # of total opportunities of the same product.
     
  • Loss Rate by Reason
    Calculating your loss rate by a specific reason gives you necessary detail to improve your win rates. How many of your deals were lost because of no budget, timelines not matching up, or feature functionality? Calculate your loss rate for each of these qualifiers to see where you need to invest your sales, marketing, or product efforts. To calculate your loss rate by reason, take your # of losses by reason / # of total losses.

These metrics should be calculated on a cadence that mirrors your sales quota cycle so that you can measure your progress. To keep these data points as up-to-date as possible, calculate these metrics at least every month and every quarter. By regularly measuring your win rates, you can monitor your successes over time and identify new opportunities for improvement.

You can make it easier to track these metrics by setting up reports in your CRM (or wherever you keep your sales opportunity data) to automatically generate these reports on a regular basis.

Qualitative Data

Qualitative data can be an incredibly useful complement to your quantitative analysis because it can uncover the “why” behind your wins and losses. The qualitative data for your win/loss analysis can be collected in multiple ways, including internal and external interviews and surveys. Internal interviews are conducted with your sales representatives to get more color behind why they won or lost specific deals. What were the main reasons that a customer signed on? Conversely, what were the main reasons the opportunity decided not to sign a deal? Understanding this from your sales representatives’ point of view will help you identify opportunities for better training, resources, or campaigns.

Internal interviews can give you insight into how you can improve your sales enablement efforts. For example, if you're actively working to improve enablement materials for a specific vertical, you can survey your sales team during this initiative to understand if they feel better equipped based on new collateral, training, etc. and which resources have been most helpful for them as they approach their deals.

In addition, you should be speaking to external sources for your win/loss interviews. You should be speaking both to customers and prospects about why they chose the solutions they chose, whether that be your solution or a competitor’s. Leveraging a third-party firm to conduct the interviews can get you more honest feedback, but in the very least having the interviewer be someone other than the sales rep involved will help you get better responses.

There are many questions you could ask to find out why you won or lost a deal; be sure to ask follow up questions to get the real “why” behind the decision. Here are some questions to get you started.

  • Were there any specific product features or services that impressed you from other vendors?
  • If all prices were equal, which vendor would you have chosen?
  • What was the most significant contributor to your final decision?
  • What was your overall experience like working with our team?
  • What was your decision-making process like?
  • What did you like/dislike most about our product/service?
  • Do you have any advice for us as we work to make our sales experience and product better?
  • Would you consider our services again in the future?

A good number to start with is about five interviews. Once you start hearing the same responses over and over again, you’ve conducted a healthy amount of interviews to begin to draw conclusions.

You can combine one-on-one interviews with customer and prospect surveys to collect more data and feedback about specific areas of interest. For example, if you find through your interviews that pricing was a key factor in many decisions, you can run a survey with more sales opportunities to gather their feedback on this specific topic.

Benefits of Win/Loss for your Entire Organization

Your win/loss analysis has benefits for multiple teams within your organization. There are benefits for your Sales, Marketing, and Product teams. For each team, you should talk through the win/loss analysis, your findings, and how your findings can benefit that team specifically.

  • Sales - Win/loss analyses help your sales teams immensely. This can be on a personal level, such as why a specific rep lost a deal, or on an organizational level, uncovering the strongest and weakest areas on the team. Both win reasons and loss reasons can be used to foster learning opportunities for your sales reps and sales organization to improve upon the sales process and ideally, win more future deals.

  • Marketing - For marketing, win/loss analyses can highlight aspects of your brand that potential customers appreciate, as well as highlight your weaknesses. This is beneficial for your marketing team because they can fine-tune messaging, adjust campaigns, and create stronger content to highlight your company’s strengths.

  • Product -  Your win/loss analysis can help drive product decisions and investments. Knowing what works, what doesn’t work, what your product is missing, and what makes your customers happy, are all great data points for your product team to build out new product features and take your product development in a positive direction.

Although a win/loss analysis can require a significant time commitment, the data you will gather during the process is extremely valuable. Not only will this help improve your sales process to increase competitive win rates, but it will reveal new ways to develop your marketing and product strategies to grow your business overall.



Ellie Mirman

Ellie Mirman

Ellie Mirman
is CMO at Crayon, the market and competitive intelligence company that enables businesses to track, analyze, and act on everything happening outside their four walls. Prior to Crayon, she was VP Marketing at Toast, where she built and led the marketing function across demand gen, content marketing, product marketing, branding, and customer advocacy. Previously, she held multiple marketing leadership positions at HubSpot during its growth from 100 customers to IPO. Ellie loves working at the intersection between Marketing, Sales, and Product, and building marketing from startup to scale-up.





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