Getting Started: How to Build the Foundations for a Successful Win-Loss Program

Successful win-loss programs start with smart groundwork.

This means securing stakeholder buy-in, establishing clear research objectives, and setting up processes that scale – all before you conduct your first interview or analyze a single deal.

Get this wrong and months down the line you’ll find yourself with scattered data, disengaged stakeholders, and a program that needs a complete and costly overhaul. 

This guide is all about nailing those critical first steps. We’ll walk you through how to:

• Secure program buy-in from key departments
• Create focused research objectives using stakeholder surveys
• Narrow down which deals to prioritize

Totally new to win-loss analysis? Check out our ultimate guide to win-loss first for definitions and best practices. 

Let’s get started!

Rally Your Stakeholders

A win-loss program is only as strong as the organization behind it.

Before you start sourcing interviews and analyzing win-loss data, you’ll need to secure buy-in with the right people. 

To do this, map out what departments at your org interact with your buyers and customer

rs and then consider what insights those stakeholders might need most. Chances are:

• Product is dying to know what features make or break deals
• Marketing is eager to validate their messaging 
• Sales leaders are interested in identifying process and execution gaps
• Executives want deep buyer insights to guide strategy and big-picture decision-making

The key is showing each group how win-loss insights will directly impact their goals. 

As VP & Co-Founder of Klue Win-Loss Ryan Sorley puts it: “The best win-loss programs aren’t built FOR leadership, they’re built WITH leadership.”

Let’s look at how to approach each stakeholder group…

Prefer to watch? Dylan D’Urso broke down how to start a win-loss program on the C&C Pod👇

CEO/C-Suite

Naturally, this is your most important stakeholder to win over. The good news? It’s typically a straightforward pitch.

Think about it – how often does your C-suite get an unfiltered view of why deals are won or lost? Their “single source of truth” is typically whatever makes it up from sanitized CRM data and second-hand sales reports

Our recommendation, start with one simple question: “Do you feel you truly know why we’re winning and losing deals?” The answer is usually no. That’s your opening.

Then, when it comes to the actual pitch, emphasize how win-loss analysis can be aligned directly with broader corporate objectives. For example, if you’re at a SaaS company that’s looking to move upmarket, show how win-loss insights will reveal crucial enterprise buyer requirements and accelerate expansion by helping you identify product gaps you need to fill.

💡 Did you know? In 2025, 98% of win-loss programs have executive visibility. For more stats like this, check our 2025 Win-Loss Trends Report (we surveyed 300+ leaders!).

Functional Leaders

Product, Marketing, Sales, and Customer Success leaders need to see direct value. And that means results, results, and more results.

The key to getting their buy-in? Show how win-loss insights will directly impact their metrics and help them hit their goals faster.

To do this, meet with each leader or send a short stakeholder survey (more on this shortly) to understand:

• What assumptions or hypotheses they hold about why they win or lose deals
• What feedback they’re missing about deals
• What questions they would ask buyers directly
• How they plan to use these insights to achieve their goals

When leaders put their thumbprint on the program design, they’ll develop a sense of ownership. This is key. 

Sales Team

Your sales team can be your biggest asset or your biggest roadblock. Many hear “win-loss” and think “deal inspection.” Here’s how to flip that perception.

First, start with sales leadership. Meet with your CRO or Head of Sales to understand their blindspots:

• What don’t they know about team performance?
• What competitive intel are they missing?
• Which buyer insights would help them win more?

Second, warm up your sellers to win-loss by sharing win interviews that highlight their strengths. Begin by interviewing customers from successful deals where your team won the business. Share these win reports openly and celebrate moments where sellers excelled. This will immediately show that win-loss isn’t about pointing fingers – it’s about honing in on success.

Third, give your sales team direct involvement in the program. Let them know early on that they’ll be able to nominate deals they want analyzed, especially ones where they need competitive insights or buyer feedback.

Set Your Win-Loss Research Objectives

With your stakeholders aligned, it’s time to define clear objectives for your program.

What Are Win-Loss Research Objectives?

Your program needs intentionality right from the get-go. Learning objectives are the specific insights you want to uncover with your win-loss program – and they should be defined in partnership with your stakeholders.

Strong learning objectives:

• Align with company goals
  • Example = “own our category by becoming the preferred vendor over Competitor X”
• Address stakeholder needs
  • Example = “understand why sales team loses 70% of head-to-head deals against Competitor X”
• Drive specific actions
  • Example = “create new competitive battlecards and objection-handling guides”
• Are measurable
  • Example = “increase competitive win rate from 30% to 50% against Competitor X”

Generally, your learning objectives will fall into one of the following categories:

• Business Drivers: The core reasons behind why buyers were exploring solutions
• Competitors: How rival solutions impacted the buyer’s choice
• Demo/Presentation: Feedback on how well your product demo resonated
• Product: What buyers loved – or felt was missing – from your offering
• Pricing: Reactions to cost, value, and pricing structure
• Sales Process: How your sales team performed and connected with the buyer
• Influencers: Who (inside or outside the company) shaped their decision
• Selection Criteria: The features and capabilities buyers cared about most

Using Stakeholder Surveys to Create Crystal Clear Learning Objectives

Now that you understand what makes a strong learning objective, let’s look at how to use stakeholder surveys to develop them. While not mandatory, this stakeholder-driven approach is highly recommended at Klue. 

Here’s how to run an effective stakeholder survey:

First, decide who will receive your survey. If you’ve followed the steps in this guide so far, you should have buy-in secured and these stakeholders should be expecting your survey:

• CEO/Executive team
• Marketing
• Sales & Enablement
• Customer Success
• Product
• Research team

Second, write your survey. Keep it short and focused – no more than 5 minutes to complete. 

Here are the core questions we like to use at Klue:

• What feedback are you missing about deals? (product, pricing, sales process, competitive intel, etc.)
• What are the top 5 questions you’d want to ask buyers directly?
• How will you use these insights to drive change in your team?

Third, distribute your survey using simple tools like Typeform or Google Forms. Don’t be afraid to send friendly reminders – stakeholder input is crucial for program success.

Finally, use your survey results to build out learning objectives. To do this, we recommend using the X, Y, Z Formula: “If I knew [X], I could do [Y], which would result in [Z]”

Where:

• X is your knowledge gap: What you need to learn
• Y is your action: What you’ll do with that knowledge
• Z is your goal: The measurable outcome you want to achieve

For example, if several stakeholders mention struggling against a key competitor and they want to understand why, your learning objective might look like this: “If we knew why customers choose Competitor X over us, we could improve our sales playbooks and feature prioritization, which would result in higher win rates against them.”

Set Up Your Win-Loss Program Structure

Once you’ve defined your research objectives, the next step is to set up your win-loss program. A program is simply a way to group related interviews with shared characteristics.

It’s common for organizations to run multiple programs focused on different segments – like separating Enterprise deals from Mid-Market, or New Business from Expansion opportunities. This segmentation helps you track patterns and insights specific to each part of your business. 

Within Klue, you can easily manage multiple programs using clear naming conventions like “Win-Loss Analysis – 2025” or “Churn Analysis – 2025”. Including the interview type, date, and segment in your program name helps keep everything organized and makes it simple to analyze trends over time.

Here’s how to create a new program in Klue Win-Loss 👇

Prioritize Your Most Impactful Deals for Interviews 

With your program set up, the next step is deciding which deals to analyze. While every closed opportunity offers potential insights, being strategic about your selection will maximize the value of your win-loss program.

Here are some things to prioritize when selecting deals:

• Learning Objective Alignment: Start with deals that directly align with your research objectives. This ensures every interview contributes to your program goals.
  
• 90-Day Window: Target deals that closed within the last 90 days. Ryan Sorley calls this the “Goldilocks Zone” – the dust has settled but details are still fresh.
  
• Late Stage Deals: Focus on opportunities that went deep into your sales process. These deals provide the most comprehensive feedback about your entire buyer journey.
  
• Competitive Deals: Prioritize deals where you go head-to-head with key competitors. Often, these reveal the most about your market positioning.

Within Klue’s Win-Loss Analytics, you can easily identify which competitors you’ve lost the most revenue to, helping you focus your research on the most impactful opportunities. This way, you can uncover the reasons behind your wins and losses and use those insights to enable your sales, product, and executive teams.

Here’s a quick demo of this feature in action 👇

Ready to Launch!

You wouldn’t build a house without strong foundations. The same goes for win-loss programs – skip the groundwork, and the whole thing could come crumbling down months down the line. 

The good news? If you’ve followed this guide step-by-step you should have: 

• Secured buy-in from key stakeholders across your organization
• Created focused research objectives via stakeholder surveys
• Selected which deals you want to prioritize for analysis

Taking the time to nail these fundamentals now will set your program up for long-term success.

Good luck!

Want to jump straight into conducting win-loss interviews? Check out our free guide below 👇