This article is based on Nick’s stellar interview with Holly Watson on the GTM-FM podcast. Pop on your headphones and listen to the interview in its full glory here!

As the President and Chief Revenue Officer of TruVoice from Corporate Visions (formerly Primary Intelligence), I’ve seen my fair share of win/loss programs – everything from a lone product marketer single-handedly sifting through CRM insights to big-budget operations run by third parties like ours. 

However you choose to approach win/loss analysis, the most measurable return on investment comes from achieving more wins and increasing your revenue.

According to Accenture, a formal win/loss program can raise win rates by 17% year-over-year. Gartner’s estimate was even higher. In our 20-plus years of doing formal win/loss at Primary Intelligence, we’ve seen some of our customers increase their win rates by over 70% in under 18 months. 

But something that often gets overlooked is what win/loss does for individuals. It creates an individual roadmap, a formula to win, for every team member. If you hear from your buyers exactly what you need to do better next time, that’s powerful. 

You understand what matters to different buyers at different times and know what you need to work on. You know you’re playing a game that you can win. When you know the rules of the game and how to win, you get engaged and committed – it’s human nature. 

Intangible as it may sound, that’s one of the biggest benefits of win/loss. It teaches product marketing, sales ops, reps, product developers, pricing teams – everyone – exactly how to enable more wins and growth in their roles. 

So, let’s dive into some best practices that are going to help you do just that.

Best practices for your win/loss strategy

Our list of best practices has grown over 20 years of doing win/loss analysis. And, of course, the best practices you need to keep in mind will depend on the size of your company and the maturity of your win/loss program.

No matter where your organization is currently, the following best practices will help make your win/loss program a resounding success.

Don’t rely purely on sales reps’ feedback 

From our conversations with buyers, we’ve seen that sales reps are wrong about why they won or lost the deal over 50% of the time. Even when they’re close to being right, they still miss key drivers behind the decision.

Now, I’m not saying that reps aren’t smart. The issue is that buyers often won’t be fully transparent with a sales rep about why they lost, to avoid hurting their feelings. It's easy for buyers to say, “You were great, but…” and blame the price or the product – things out of the sales rep's control. So, relying solely on rep feedback is not truly embracing win/loss analysis. You need to incorporate buyer feedback.

Get feedback from as many buyers as possible

Our second best practice focuses on the volume of win/loss interviews. Oftentimes, when win/loss analysis is owned by product marketing, it’s one of many hats they wear. It’s not their priority, just one more thing on their plates. 

Then product marketing tries engaging sales, who fold their arms, saying, “That’s your job; I’m selling.” Or they find 100 reasons to exclude a deal from the win/loss analysis, fearing it may expose something or hurt the relationship. 

But buyers expect to give feedback everywhere. You even give feedback when checking out of the grocery store! So why do we fear asking buyers why they bought or didn’t? Why worry it will ruin relationships? 

If you're only doing 15, 20, or even 100 buyer interviews, that's likely not enough (unless you only do 100 deals in a year). You should interview as many buyers as possible – won, lost, churned, renewed, even those stalled no-decision deals that sales leaders hate.


Well, let’s say you’re a product marketer, and you’ve spent an entire year wrestling contact info from your sales teams’ hands so you can interview buyers. It’s finally time to present your win/loss insights to executives. You march in ready to conquer the world, with PowerPoints, videos, and data, pumped to share insights that will blow their minds and get a standing ovation.

But then the head of sales says, “Fantastic job! How many data points does this represent?” Unless you have at least 25% coverage of the full deal universe, they’ll discredit it all, like, “Great job, give us another report next year,” and it's back to the status quo.

So, why is volume so critical?

Although volume brings credibility, it often gets overlooked. I see big companies budget for 20 interviews a quarter and think – great, what else will you do? With all the feedback mechanisms and mediums that are available today, there's no reason you shouldn't ask about every single deal, won or lost. Volume lends credibility and ensures you capture all the insights you need to drive change.

Here’s the other reason that volume is so important: it allows you to provide not just top-level insights but insights down to the individual sales rep level. 

If you tell the sales force, “We did 25 interviews and learned that we need to improve our product demos,” that data means nothing to them. Your individual reps will be sitting there thinking, “Pfft! That's just Ralph's deals. My demos are great. I'm gonna keep doing what I'm doing.”

But if you say, “Lee, this is what your buyer said specifically,” now you have their attention, and they’re going to change their behavior. So, volume drives leadership-level credibility for your win/loss program and gets engagement and buy-in to change from reps.

How to gather win/loss data at scale 

If you're thinking, “How on earth am I going to be able to gather insights on at least 25% of my deals?” you're in good company – this is something I hear a lot. However, it doesn’t have to be a massive undertaking. 

Apart from interviews and CRM data, survey tools like SurveyMonkey or Qualtrics can be a good place to start. Some organizations even provide survey experiences that feel almost like an interview, allowing you to gather qualitative intel rather than just quantitative data.

At Primary Intelligence, we have a tool that provides full automated coverage. You can almost set it and forget it, allowing you to focus on conducting robust interviews for deeper insights.

In an ideal world, every organization would have the budget and resources to hire a third party to conduct interviews so PMMs could focus on analyzing and disseminating insights rather than running the program. 

However, if all you can afford is five interviews plus rep feedback, that's better than nothing. Just be aware of the credibility risk associated with limited volume.

Getting your first win

Whenever you’re launching a new program, it’s important to bag some quick wins. That’s how you get the rest of your organization excited about what you’re doing. 

To find your first win with win/loss, start by talking to a won deal. Let’s say you won a deal with Amazon. If you ask your sales leader for the secret to that success, they’re just going to say, “Our sales rep is amazing!” I’m sure they are, but that feedback isn’t going to help you replicate their success. You need to keep digging.

They should be more than happy for you to talk to the buyer – after all, you’re celebrating their success, not looking for trouble. Then, once you interview the buyer, you’ll have a more tangible, replicable idea of just how such a competitive deal was won. And be sure to celebrate what you find: “Holly just won the Amazon deal by doing X, Y, and Z!” 

Then, you can just keep going. Focus on the wins for your first 10 or 15 interviews, and you’ll start building momentum and excitement. After that, when you’ve got internal buy-in and your win/loss program is starting to take shape, you can start layering in losses and no-decision deals. 

How to extract maximum value from your win/loss program

If you own a win/loss program, your time should be spent analyzing insights, not administering the program. That’s why third parties exist – I know sometimes you own the nuts and bolts, it’s just set up that way. I see you and feel for you! But when possible, engage a third party so you can focus on tying insights to go-to-market improvements.

There are so many places where your win/loss insights can drive improvements. With enough data and the right questions, you can use win/loss analysis to identify your ideal customer profile and personas.

And here’s an important tip: don't just ask the main customer contact for feedback. Talk to the whole buying committee to understand what drove the decision from every perspective – the budget owner, other influencers, and end users. That allows you to build persona maps and buyer journeys.

Win/loss programs are useful for marketing, too, as they provide intelligence that informs assets and campaigns. However, the usefulness of win/loss insights is not limited to sales and marketing alone; they can also help customer success teams optimize their onboarding, adoption, and renewal discussions.

If your win/loss program is only being used for one part of the customer journey, it’s not being fully utilized. It should inform every moment that a buyer is making a decision.

Get started today

Before we wrap up, I just wanted to encourage you to get started with your win/loss analysis. It's not as daunting as it may seem. You can start small with a handful of buyer interviews – and you don't even have to use a third party for it; you can do it internally. 

The pandemic changed everything about how buyers make decisions – from procurement processes to legal negotiations. That means understanding why you win or lose deals is more important than ever. You'll also notice that your competitors are adapting and innovating to stay ahead of the curve, which means you might face new competition in your industry. 

But don't worry. You don't need to do everything at once or scale it immediately. You're not alone, and you can start taking baby steps today. So, let's get started!