Empowering Win-Loss Analysis: 5-Steps to Success

Empowering Win-Loss Analysis: 5-Steps to Success

Jordan Weaver
Jordan Weaver
10-minute read

Follow this 5-step win-loss analysis guide to help you effectively improve sales numbers, marketing messaging, and the product pipeline to gain a competitive edge.

Table of Contents

  1. What is Win-Loss Analysis
  2. How is Win-Loss Analysis Measured
  3. Successful Win-Loss Analysis in 5-Steps
  4. Essential Focus Areas for Win-Loss Interviews
  5. Win-Loss Companies: Game-Changing Benefits
  6. Where Win-Loss Research Fails
  7. High-Impact Win-Loss Program
  8. Let's Get Started with Win-Loss

What is Win-Loss Analysis

Win-loss analysis is a research technique that involves gathering feedback from customers and prospects to understand the factors that influenced their decision to buy or not to buy from your company. This type of research often falls under the umbrella of competitive intelligence.

It is a process of systematically evaluating the factors that led to winning or losing a deal, with the ultimate goal of improving the overall sales performance, messaging and positioning, and product pipeline prioritization. The way we at Anthroware have positioned ourselves to be one of the most white-glove software development companies for the last 10 years has given us an edge on conducting this type of in-depth research.

The analysis typically includes in-depth interviews with buyers, decision-makers, and influencers to gain a comprehensive understanding of the entire sales process from their perspective. Deep insights can be extracted from this qualitative dataset that can be synthesized into actionable recommendations to drive impact across a business. Some companies, as we do at Anthroware, have even started leveraging AI tools to extract data in ways that even some of the top AI companies are.

The Powerful Role of Win-Loss Surveys

Some companies like Anthroware will also run a supplementary survey alongside the interviews to compile a quantitative dataset that can validate or invalidate the scale of relevancy of the hypotheses found in the interviews, but that's a more complex business-level strategy we'll save for another article solely on the topic of win-loss surveys.

In this guide, we will delve into the 5-steps for conducting an effective analysis, and how to use the insights gained from it to win more deals, generate more/higher-quality leads, and ensure the features and products you're launching are the most relevant to your total addressable market (TAM).

Why Conduct a Win-Loss Analysis

The feedback gathered from these programs can help you identify areas of strength and weakness in the following areas:

  • Sales process and value proposition
  • Go-to-market strategy, messaging and positioning
  • Effectiveness of your product pipeline prioritization and product-market-fit
  • A better understanding of the overall competitive landscape
In fact, according to Ellen Naylor from The Business Intelligence Source (TBIS), 'companies properly utilizing this analysis will find that it produces the best actionable intelligence available, purely from their sales results'. Naylor, Ellen. "Increasing sales through win/loss analysis." Competitive Intelligence Magazine 5.5 (2002): 5-8.

At Anthroware we've found this to be true, especially when using the mix of win-loss surveys alongside the interviews.

How is Win-Loss Analysis Measured

Measuring success isn't rocket science, in fact, it's quite simple. There are two ways to look at it, win rate, or win-loss ratio. The number of won opportunities divided by the total number of opportunities in your pipeline equals your win rate, the measurement of how often (percent of the time) you are winning deals. The number of won opportunities divided by the number of lost opportunities in your pipeline equals your win-loss ratio, the measurement of how frequently you are winning deals versus losing them.

To put this simply, if your win-loss ratio is greater than 1, that means you are winning over 50% of your deals. You are winning more often than you are losing.

If your win-loss ratio is less than 1, you are losing over 50% of your deals. You are losing more often than you are winning.

Research cohorts for diving deep

For measuring, you wouldn't look at the entire customer relationship management (CRM) database when calculating your win rate or win-loss ratio. The idea is to try and get more granular with whatever research cohort aligns the most strongly with whatever business objectives your stakeholders are trying to tackle.

For example, starting with a segment of your pipeline that has a very specific ideal client profile (ICP) and calculating the win rate or win-loss ratio for that, is going to be easier to monitor over time versus your entire pipeline.

Measuring Win Rate with Win-Loss Analysis
How is the Win Rate Measured?
Measuring Win-Loss Ratio with Win-Loss Analysis
How is the Win-Loss Ratio Measured?

But what about marketing and product?

While your win rate and win-loss ratio are pulled from sales, you might be wondering how we measure our success with product marketing and the product pipeline. As we mentioned above, those are other main focus areas. Marketing is usually more focused on things like demand generation, lead quality (alignment with sales), and brand awareness.

Product pipeline prioritization is more focused on making sure the product roadmap is delivering new features and products that are in the highest demand to help win more deals, drive more demand, and increase overall customer satisfaction and customer lifetime value. Another side bonus is how much these programs help with building a strong team.

Competitive example

For example, if a trend is identified in which customers are going with a competitor because marketing didn't advertise a certain feature, or the platform is actually lacking the feature, the product roadmap can prioritize that by either adding it or bumping its launch up a few quarters. Marketing can follow and start advertising that the new feature or product will be coming soon, to start driving awareness and leads.

Anthroware's steel thread - research

As you can probably imagine, measuring effectiveness for product marketing and product pipeline is much more nuanced than the sales win rate or win-loss ratio. Our 10 years of experience in strategic consulting and product R&D has provided us with a few strategies we like to deploy here, but that's an entirely separate article on its own.

If you aren't currently able to identify your win rate or win-loss ratio, a good place to start is with more basic 'sales win-loss analysis' and to first set up a solid system of win-loss record-keeping.

Successful Win-Loss Analysis in 5-Steps

At Anthroware we've identified these key 5-steps to be the most successful ways to spin up, conduct, and deliver a valuable W/L program.

We'll dive into these more below and highlight some reasons for using this win-loss research framework.

5-Steps for a Successful Win-Loss Analysis
5-Steps for a Successful Win-Loss Analysis
5-Steps for a Successful Win-Loss Analysis
5-Steps for a Successful Win-Loss Analysis

Step 1. Establish a baseline and determine business objectives

From our years of experience in product strategy, we've learned a solid baseline is one of the most important components of research.

Dig deep into your data and outline desired outcomes/goals.

  • Be prepared to spend more time upfront to get things going, watch the time, but we make the margin based on the length of the contract.
  • Our partners will have a treasure trove of B2B competitive intel already. Get access to this and rigorously learn/evaluate.
  • Interview stakeholders to deeply understand their needs (product leaders AND sales/marketing leaders if possible).
  • Find out how to zero in on a few key knowledge gaps. The more focused we can be learning about an organization, the more focused and actionable the intel we provide will be.

Step 2. Define a seamless process for extracting data

Work with the client’s sales leaders and/or customer success leaders to implement a process to incentivize closed deals into our interview funnel

  • How and when do we incentivize customers into our interview funnel?
  • How will we utilize surveys (i.e., as interview funnel intake source? or validation?) and agree on expectations for the data we get from them?
  • Agree on incentive packages (Amazon gift card, etc.)

Step 3. Customize to your stakeholders and teams

What questions do we know to ask? What are areas where we know something is up, but can't put our finger on it?

This is where we define a business strategy for the interviews and surveys.

  • Key stakeholders (hopefully C-Level or Regional) will have specific questions or gaps in understanding. Meeting their needs and having them feel heard is super important.
  • Gather knowledge of ‘change agents’ within the client organization – People that are uniquely positioned to accept actionable recommendations and successfully implement them in order for clients to see outcomes. The 80/20 rule applies here (80% of work within many organizations is done by 20% of their employees). We want these employees involved even if they aren't stakeholders.

Step 4. Execute and synthesize data/insights into actionable intelligence

Conduct the interviews, analyze raw data, and work with your team to turn data into wisdom

  • Run the interviews.
  • Be curious!
  • Compile thoughts as we go and be the neutral third party when it comes to insights.

Step 5. Periodic reporting for stakeholders and change agents

The main value we add at Anthroware is critical thinking and analysis to make the most of your digital storefront. It isn't just about patterns and insights. We make recommendations, when possible, and act as an extension of your sales, marketing, and product teams (which also makes us unique to most other digital transformation consulting firms and win-loss firms out there). Think of us as your action-to-impact partner.

  • Show results that can be quantified clearly.
  • Show qualitative results/comments/insights as interpretive and have clear reasoning for any conclusions we draw from the data.
  • Create a deck and present findings. This includes summaries of actionable recommendations and the potential impact they will have across the business.
  • Get as many people involved to ensure action is taken and that your win-loss program doesn't just exist as more useless "shelfware".
Win-Loss Analysis
Win-Loss Analysis

Essential Focus Areas for Win-Loss Interviews

This portion serves to highlight the custom ways that we adapt our interview and survey process through meeting with stakeholders that have the highest stake in the success of the company. It’s their sensitivity to company goals, vision, and priority initiatives that serve as our compass for conducting the rest of the win-loss research.

Pre-sales engagement

Includes the initial motivation for searching for sales software, initial brand perceptions of individual companies, and perceptions of market leaders. Having really effective team communication between our company and our partners really helps build a strong foundation for these programs, and that's what we're experts at.

Sales timeline

Covers the initial contacts with companies, changes in perception, external factors, and demonstrations.

Sales experience

Examine whether the customer felt that the companies they spoke to fit their use case and why or why not.

Customer Success

Understand time to value, ease of implementation, and the customer service experience perceived by clients. If this is a priority, a customer retention program might be the best fit for your company instead of a win-loss program.

Product and Solution

Assess missing or excessive features, integrations, and UI/UX comparisons. Keep in mind some human-centered design examples related to our partner's products and try to determine if fixing the design is a big part of the product usage problem, if there is one.

Pricing and Packaging

Evaluate the clarity of pricing, surprises, and preferred pricing structures.

The win-loss interviews also include questions about the perceived future state or partnership potential with the company vs their competitors, customer service, and any negatives in the sales process. Finally, we ask customers to rank the following in order of importance: ease of use, ease of implementation, price, features, and customer service. We do this to extract as much data and insights as possible with our W/L program.

Win-Loss Companies: Game-Changing Benefits

Many people believe win-loss companies to be purely dedicated to supporting sales teams. Anthroware believes this couldn't be further from the truth! Sales, marketing, and product management should all benefit.

Sales Leader Outcomes

  • Identify process or sales experience issues.
  • Hear about competitor strengths and weaknesses.
  • Continuous improvement in sales efforts.
  • Address specific stakeholder needs in an agile way (90-day learning sprints)
  • Faster learning cycles and more surgical application of funds

Outcome = increased win rate = increased revenue! (Near-term KPI)

Marketing Leader Outcomes

  • Refine go-to-market messaging based on real-time market feedback
  • Gain a deep understanding of product-market-fit even as the market is changing
  • Identify crystal-clear buyer personas
  • Understand the importance of customer behavior analysis
  • Speak with customer success and customer experience to determine the effectiveness of current customer retention strategies
  • Obtain a broader understanding of the voice of the customer beyond your installed base

Outcome = increased TAM = increased revenue! (Mid-term KPI)

Head of Product Outcomes

  • What experiences in our product don’t compete in the market and need our attention?
  • What’s missing?
  • What’s working well?
  • Insights to prioritize product roadmap with what sells.

Outcome = increased TAM = increased revenue! (Long-term KPI)

Value is driven from the bottom up and deep insights should be applied at all levels of the product lifecycle.

Where Win-Loss Research Fails

When we began these programs for our customers, we decided to spend a ton of extra time doing our own market research and competitive research (and leveraging data from our competitive intelligence software partner, Crayon) before deciding how we were going to structure our programs. We wanted to have a clear understanding of which processes and philosophies would deliver the highest value to our customers.

Below are some common challenges we see in companies running internal win-loss research or even sometimes using another win-loss partner. Keep an eye out for them - they could cause your win-loss program to fail on delivering high value!

Some of these challenges are easier to solve than others. We've developed unique approaches to some of these based on our expertise in strategy and product.

  • Level of expertise of the interviewer - don't use a survey shop, use someone who has a high level of knowledge.
  • Biased data or lack of candid data - this is where a 3rd party win-loss partner is helpful, to extract more truthful data.
  • Running the same survey quarter over quarter - don't do this unless the study is extremely specific. Markets change, so do business objectives, so should surveys.
  • Keeping sales in the dark - this is the best way to have a low conversion rate of opportunities to interviews. You want sales to be involved. Get them excited about how much they are going to learn and improve. Allow them to be the champion here!
  • Actionable recommendations - if you aren't getting these from your win-loss program, what's the point? More data doesn't solve core issues within a business, taking action does. This is where critical thinking becomes one of the most important aspects of your win-loss program to synthesize data and insights into action.
  • Including change agents - aligning them early on with stakeholders and business objectives will help get them on the same page and understand how to take action and start driving impact.

If you're experiencing any of these challenges with your win-loss program, let's get started together and discuss if we can help you figure out a solution. Just like it's not easy to understand how to choose your ideal software development partner, we know it can be tough to understand which direction to go for win-loss.

High-Impact Win-Loss Program

If you're curious to learn more, feel free to check out our win-loss case study from our research with Salesloft, which provides an example of how impactful this type of B2B analysis really can be for your company.

By understanding the factors that contribute to sales successes or failures, businesses can make targeted improvements. Whether that means improving the sales process, refining messaging, reprioritizing the product pipeline, or developing strategies to differentiate themselves from their competitors, there are many different areas of focus that businesses can choose from.

With the right process and a commitment to continuous improvement, this can be one of the most powerful foundations in your business's arsenal for driving success and achieving business growth.

If you're ready to dive right in and start talking about how win-loss can affect your business, let's get started with the link below!

Let's Get Started with Win-Loss

Click our contact page at the top of our page to visit Anthroware's and start receiving help for building out your company's win-loss analysis today.

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.