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win-loss analysis

Unlocking True Value from Win/Loss Analysis: A Product Marketing Manager's Guide

Product marketers: Want cross-functional alignment, sharper marketing, and better competitive insights? Try a win/loss analysis. Here's how to get started.



As a product marketing manager, your role revolves around bringing teams together. In fact, making sure everyone in your organization is on the same page is vital to the success of your positioning, messaging, and go-to-market strategy.

So when you hear Manny in sales saying you win because of price while Mina in product tells her team you win because of your reporting feature, what can you do to get cross-functional alignment?

Embracing win/loss analysis is a spectacular first move.

Because once Manny, Mina, and the rest of your organization are aligned on why you win and lose, you're not just aligned. You're also poised for exponential growth and new opportunities.

This article will help you gain the confidence to conquer even the biggest challenges in building a win/loss program. 

Win/loss can be a win/win for your organization.

What is a Win/Loss Analysis?

A win/loss analysis is the process of gathering intelligence to answer these nagging questions confidently;

  • Why do we win deals?
  • Why do we lose deals?
  • Why do we keep customers (who often upgrade)?
  • Why do we lose customers?

Through this process, you'll learn more about what your customers and potential customers need and prefer. You'll see where your solution shines (your strengths) and where it needs improvement (your weaknesses).

This investigation will also reveal market trends and competitive threats your company should know about -- and act upon.

Who Benefits from a Win/Loss Analysis (Besides Sales)?

The intelligence you collect benefits nearly every team in your organization. Here is a sampling of win/loss benefits, explained team by team (starting with sales)

Sales enablement. Win/loss data gives sales leaders a clear understanding of why their team wins and loses. These analyses often reveal what customers and prospects liked or didn't like about the sales process.

With these insights, sales leaders can adjust training and materials to win more deals

Product management. Product managers use win/loss insights about a solution's features and functionality to guide product development. For example, they prioritize the product roadmap based on features that customers and prospects commonly mention when discussing wins or losses.

Product managers also review these insights to improve the customer's overall experience with the solution.

Customer success. Customer success managers use findings to improve customers' onboarding experience. With a better understanding of how customers justify their investment in your product or service, they can better track success metrics and reduce churn.

C-suite. For company executives, win/loss trends provide insights into market trends, prioritize resources for key teams, and identify potential areas for future investment.

Product marketing. Now let's talk about you. You create these analyses for the company, but you're the key beneficiary in the end. (Let that be our secret!)

For example, did your investigation reveal that the value proposition you've used throughout your positioning has fallen flat with prospects? Use that knowledge to refine and optimize your value proposition and its associated positioning and messaging to resonate with more prospects.

Win/loss analyses are usually brimming with competitive intelligence ... another gift for your positioning and marketing efforts. Have you won or lost deals because of competitor pricing, functionality, or customer support? Use what you learn to refine your positioning and messaging to better match your target market's needs.

Competitive intelligence also provides excellent insights into market pricing. Did you lose prospects and customers because competitors offered them better deals? Take the information you gather to align your product strategy with market expectations.

And remember to use these insights to get more sales wins! Transfer the key competitive takeaways to create sales assets like Battlecards to boost your sales team's competitive win rates.

How to Calculate a Win/Loss Ratio and Win Rate

Before we delve into the win/loss how-tos, let's clarify some win/loss terms:

A win/loss ratio measures how many deals are won and lost in a given period. To get this ratio, divide the number of won opportunities by the number of lost opportunities.

Say you've won 80 deals and lost 40 deals this quarter. The computation would be 80/40 = 2.0 (or 2:1).

To calculate your win rate from those 120 opportunities, divide the number of won deals (80) by the number of total opportunities (120). Then, multiply that number by 100.

(80/120) x 100 = 66.66%

Get your loss rate by dividing the number of lost deals (40) by your 120 opportunities. Then, multiply that number by 100.

(40/120) x 100 = 33.34%

A win/loss analysis differs from win/loss ratios and win/loss rates. This analysis qualitatively peeks into the win/loss ratio and win and loss rates to uncover the impetus behind those numbers. In doing so, it's a more complex, multi-step process that takes place, at a minimum, for several weeks.

The analysis often includes win/loss ratios and win or lose rates as data points. These measurements are usually sprinkled throughout an analysis to describe how an organization wins by various job titles, regions, or verticals.

Kompyte includes this in your dashboard and does the math for you:

win-loss-kompyte (1)-1


How to Conduct a Win/Loss Analysis

If you want your work to drive company success, you'll need to mark off a few essential tasks on your win/loss checklist.

"By following best practices like structured surveys, cross-team collaboration, and a commitment to continuous improvement, PMMs pave the way for a successful win/loss program that fuels growth and customer satisfaction." - Samia Barud, PMM at Stripe

Let's talk about these must-dos for a great win/loss project.

Gather internal data. Start by searching every corner of your organization for intel. You'll be surprised how much win and loss information is hidden away!

Speak to department heads in sales, product, and customer success to see what goldmines of customer information they have to help you with this project. CRM data, NPS scores, recent surveys, and review site feedback are all good places for them to pull intelligence for you. (These colleagues might surprise you with win/loss goodies in other unexpected places!)

While you have their attention, ask them why your company wins and loses. Ask the same of the C-Suite. Answers from these stakeholders will better gauge current company alignment (apart from just Manny and Mina disagreeing). 

Conduct interviews. Interviewing the marketplace is a crucial step to support or refute the materials and opinions you've collected. Speak with a mix of prospects and customers, won deals and lost deals.  Uncover insights into the customer or buyer's:

  • Job and responsibilities
  • Business drivers for finding a solution like yours
  • Buying process (including selection criteria)
  • Perception of your brand, solution, and pricing versus the competition
  • Experience with your sales team

You can hone In on just a few of these areas. As Jason Oakley from Productive PMM explains,

“Win/loss programs give you the most actionable insights when you focus your cohorts on specific themes. Randomly selecting interview candidates based on wins or losses will get you a broad range of feedback. The more targeted you can get, the more reliable your findings will be. So be intentional and pick a theme each quarter, like losses to a specific competitor around a specific use case, or wins in a specific market segment, etc.” -- Jason Oakley, Productive PMM

However you form your interview questions, customer stories will make your analysis fresh, recent win and loss details, and give your storytelling in that analysis extra oomph. And whose writing couldn't use some extra oomph?

You can also work with a firm specializing in win/loss interviews. Kompyte now integrates with win/loss reports from research firm IcebergIQ. They have a knack for getting candid, in-depth feedback and distilling it in a way that’s easy to digest and share. 

Synthesize data. Once you've gathered internal data, stakeholder opinions, and market interviews, it's time to analyze. Start taking notes and look for recurrent themes. Organize your findings by segment (vertical, region, company size). Based on your findings, offer suggestions and actionable next steps for each functional group in your company.

Present your findings. Your goal is alignment, so make sure your insights reach as many people as possible. Ask to present your findings at a company-wide meeting. 

First, describe the scene before the analysis: that misalignment about win and loss reasons. Refrain from mentioning poor Manny and Mina by name, but share anonymized results of your earlier stakeholder win/loss questions to illustrate the current state of misalignment.

Quickly follow that up with the benefits of win/loss analyses across your organization. Highlight the potential for growth and increased profitability through leveraging win/loss analysis insights. For additional impact, mention a potential loss of the company not implementing these insights.

This will give your company more incentive to listen up. 

Touch upon top-level, relevant discoveries and actionable takeaways for each department. Then, offer a link to the full report for colleagues to learn more.

At the end of your presentation, offer a link to the full report for colleagues who want to learn more.

The Biggest Challenge in Building Win/Loss Analyses

So far, we've hinted at the heaps of discoveries you'll find in this process. Yay!

And if you popped those discoveries in a document, it could easily fill 50 pages. Yay!

Although this disclaimer might temporarily burst your enthusiastic PMM bubble, a helpful win/loss guide needs to warn you: Gathering all those win/loss discoveries and then distilling those 50 pages into something the entire company will use to stay aligned takes an incredible amount of time.

Ask a PMM who's gone through it. (Sigh.)

Luckily, there are two keys to overcoming this challenge.

First is to know that there is a bucket load of time involved. Check!

The second is to streamline the win/loss process to extract the most value from your discoveries so that your organization can reap all the benefits mentioned in the article.

Best Practices for a Win/Loss Program that Sticks

Engage stakeholders in the process. Get internal stakeholders on board as early as possible and maintain communication with them.  This early, ongoing communication will optimize your chances of aligning their teams with your win/loss findings.

Solve that time challenge through technology. Put that Time Challenge in the rearview mirror with software and AI. Find out if your sales enablement software offers or integrates with win/loss software. 

For example, Kompyte provides detailed win/loss statistics, including your company's overall win rate and which of your competitors are most formidable. Now with our integration with IcebergIQ, you can also get candid insights into the reasons you win and lose from real prospects - right inside Kompyte.

Win-Loss product animation

The integration funnels IcebergIQ win/loss interviews into Kompyte where KompyteGPT quickly summarizes key themes of the interviews. PMMs can use these summaries and customer quotes on the same platform to update their Kompyte win/loss Battlecards and help their sales team increase wins. 

"IcebergIQ has become an extension of our team, and the invaluable insights we get from their research have helped us hone our messaging, better understand competitors, and make more informed decisions. "
- Lindsay Kocel, Director, Product Marketing, TaskRay

These summaries will provide an easily digestible, single source of win/loss truth from the entire company. Talk about alignment!

If you want to take a first step toward win/loss alignment, try this win/loss Battlecard template. Many B2B SaaS companies rely on it daily to stay competitive and win more deals.


While you might initiate win/loss analysis to keep your entire organization in step regarding why you win and lose, you'll soon see other benefits from your work. Your discoveries provide clear guidance for product marketing, sales, and customer success to connect more effectively with the marketplace.

And more effective connection = more deals won (and won back).

With an organized plan, stakeholder engagement, and an assist from AI, your win/loss program will fuel your company's sustainable growth and success. And you'll get Manny and Mina to agree. Again, a total win/win!

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