Win-Loss Analysis

Want to Sell More? All you Have to do is Ask.

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You Need This.

Why Win-Loss Analysis?

The reality is that most companies don’t know the real reasons why they lose deals. Sales reps tend to blame budget, product, or competition, and customer feedback to you, the vendor, is not always forthcoming. Use Thirdside to conduct win-loss interviews on your behalf and gain candid insights into your customers’ decision-making process.

Increase Win Rates

You don’t even know why you win or lose. Customers aren’t telling you the full truth, but they will tell us. Use that intelligence to win more deals

Improve Competitive Intelligence

Customers will share more information with us about your competitors that they won’t share with you: product features, promotional strategies, pricing and more.

Win Back the No-Decisions

Get an immediate revenue bump from the no-decisions, long-maybes, and ghosted accounts.

Book a Discovery Call

Let’s see if there’s an opportunity to work together.


From blind spots to bright spots. Light your path to winning.

Every B2B organization has blind spots – those things you think you’re doing well, but that don’t resonate with buyers. It could be product features, sales tactics, or competitive maneuvers. The reality is, you simply don’t know.

Win-loss analysis illuminates these blind spots, helping you align your strategy with real customer needs and perceptions.

Revenue is Waiting

Win-Loss Analysis:
Why Now?

If you aren’t addressing blind spots, then you are continuing to lose. Even as you are reading this, the shortcomings and blindspots slowing revenue persist. Find them. Fix them. Now.

Is your go-to-market motion suffering from any of these? (And do you even know? Really know?)

  • Lack of Discovery
  • Failure to connect to customer pains
  • Generic demonstrations
  • Undifferentiated positioning
  • Missing features

What’s the Fix? (WTF)

Thirdside: Your Partner in Problem Solving

We understand your situation better than most. We’ve carried sales quotas, run marketing departments, and managed product lines. We take our in-the-trenches experience into every project, interview, and report for our clients. (We’re not burning through interviews to populate a hard-coded dashboard.)

An Eye for Revenue

Unlike career researchers, who tend to be academic in their approach, our team members are all experienced sales & marketing professionals, who pull and probe on the right experiential threads, uncovering blindspots beyond your initial line of thinking.

Safe Space for Discovery

By removing any hint of sales pressure or bias from the vendor perspective, we get much more candid responses – both positive and negative – than our clients can get on their own.


Win-Loss Analysis Reporting:
For You in Your Preferred Formats


Detailed Interview Reports

Summarized, tagged, highlighted, and linked text make it exceedingly easy to scan a report for the highlights, or quickly jump to the tags of interest.

Regular Review Calls

Guided discussions about recent interview reports provide an opportunity for stakeholders to ask questions of the Thirdside researcher who conducted the interviews.

Online Dashboard & Reporting

Thirdside includes online and completely tailored dashboards where stakeholders can access charts, anecdotes, insights, and full interview reports and run ad-hoc queries of the data.

Management Summaries

Thirdside provides periodic executive presentations in support of management meetings, business reviews, kickoffs, board meetings, etc.

You can’t Fix what you can’t see

Example Blindspots Revealed

Every company has blindspots. Only Thirdside has the flexibility in research & reporting to find them and report them so you can fix them.
The examples here are just a sample of what we’ve uncovered in the buyers’ journeys.

Sales Process
Customer Success
RevOps & Enablement

Marketing Blindspots

  • What buyers are saying about us without us?
  • How do buyers perceive us vs. competitors against their criteria?
  • How do our marketing initiatives impact buyer decisions and our deals?
  • What messaging and content resonates with our ICP?
  • What pains and decision criteria are at the top for our buyers now?
  • How is the customer experience and satisfaction?

Sales Blindspots

  • What are all the true reasons we win/lose deals?
  • What pains and decision criteria are at the top for our buyers now?
  • Are we losing deals to do-it-yourself, competitors, or do-nothing? 
  • What sales have done well/can do better to win business?
  • What are our sales skill gaps, and what do reps need to know about buyers to win more?
  • How do buyers perceive us vs. competitors against their criteria

Customer Success Blindspots

  • What makes our clients churn and drives retention or renewals?
  • What specific clients are at risk of leaving right now?
  • What should we do to win back churned clients?
  • How is the customer experience after the sale?  
  • What skill gaps are in CS that prevent us from renewals? 
  • What do CSMs need to really know about our clients/users to drive expansion?

Product Blindspots

  • What features of our solution are differentiators or lacking?
  • What product gaps should be prioritized in our roadmap?
  • How should we refine product strategy for ideal positioning?
  • How can we influence our firm with credible data and drive product adoption? 

RevOps & Enablement Blindspots

  • What skill gaps are in sales and customer success to win the market? 
  • What do reps/CSMs need to really know about our buyers to win?
  • What is the impact of our partners on our sales efforts?
  • What’s the impact of our enablement programs on deals over time?
  • What are all the true reasons we win/lose deals?
  • What messaging and content resonates with our ICP?


Win-loss analysis can improve win rates by up to 50% and revenue by 15-30%. (Gartner)


Rigorous Win-loss interviews, on average, increase win rates by 18%. (Accenture)

The pessimistic
business case?

If your annual revenue target is $10M and you have a 20% win rate, only a 10% improvement in win rate as a result of win-loss analysis means an additional $1M in revenue every year.



Find answers to frequently asked questions about the win-loss analysis process, benefits, and Thirdside’s unique approach.

What is win-loss analysis?

Win-loss analysis is the process of interviewing recent sales wins, losses, and no-decisions to gain insights and identify blind spots in your sales pipeline.

Why is win-loss analysis important?

Win-loss analysis is important because it helps companies understand why they win or lose deals, uncover areas for improvement, and make data-driven decisions to enhance their sales strategies.

How does Thirdside conduct win-loss analysis?

Thirdside conducts win-loss analysis by conducting in-depth interviews with customers, leveraging their experience as business professionals to uncover meaningful insights and identify blind spots.

What are the benefits of win-loss analysis?

The benefits of win-loss analysis include gaining a deeper understanding of customer needs, improving sales effectiveness,

Still have questions?

If you have any more questions about win-loss analysis or how Thirdside can help your business, please contact us.

How can I get started?

To get started with Thirdside’s services, simply reach out to us through our contact form or give us a call. We look forward to discussing how we can help your business.

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