This article has been adapted from Penny’s brilliant interview with Erik Mansur on Into the Fray: The Competitive Intelligence podcast. Listen to it in its full glory here!

Looking to gain a competitive edge? A robust win/loss program just might be the answer – and I’m here to help you build one. 

Here’s what we’ll cover: 

Strap in and get ready to discover how win/loss insights can drive real change across your organization!

Leveraging the voice of the customer in win/loss analysis

Early in my tenure as Head of Competitive Intelligence at Zuora, I was being pushed to focus mainly on aligning with the sales team and debriefing them on deals. While aligning with sales teams is, of course, vital, I knew this approach was missing one key ingredient: the voice of the customer (VoC). 

When you bring in an external perspective and talk to the customer directly, you gather much more valuable insights. At a previous company, I’d worked alongside market researchers who spoke to customers daily. Their feedback shaped our strategies and drove real change.

Yes, there's value in having win/loss conversations with your account teams, but they tend to be a little bit biased. Not only are they biased, but they don't always know why they won or lost. 

Zuora needed to incorporate customer insights more fully. So, after researching best practices, I introduced a formal win/loss intelligence program. My goal was to build a world-class program that would generate actionable intelligence for the whole organization. 

I established a continuous process of interviewing customers each quarter to find out why deals were won or lost. At the end of the first quarter, I created a report to share the insights I gathered. I also sat down with each of the functional product leaders to discuss the insights in their leadership team meetings and try to drive action. 

The first report was well received, but it wasn't until the second quarter that the new win/loss program gained traction. That’s because it took a little time to be able to gather enough data to identify trends – and of course, trends are hugely important when it comes to spotting opportunities for systemic change.

Partnering with sales

Getting the sales teams’ buy-in is essential for the success of any win/loss program. However, I saw a little hesitancy from my sales teams when I first asked them to provide contacts for customer interviews. I could understand their reluctance – they might think I was spying on them or monitoring their performance. 

Even as sellers started to embrace the program, when I looked at our customer relationship management (CRM) system, I could see in the closed notes that they were still trying to get feedback from the prospect or even reverse lost deals. 

Meanwhile, I was encouraging them to put accounts through the program, rather than quizzing prospects themselves. We use an external consultant who’s great at these kinds of interviews. She has a talent for digging deep to uncover insights beyond what salespeople can do on their own. 

However, as soon as sellers started to see actionable insights – real strategies for boosting their win rates – coming out of the win/loss program, they loved it. 

Balancing qualitative and quantitative insights

When you’re tasked with building a win/loss program from scratch, it can be hard to know where to start. So, I invested in some training, which was invaluable in helping me get my program off the ground. 

One of the best practices I gleaned was having a sample size of about 20 deals to work from, so that became my goal. However, when you’re selling to enterprises, the reality is that you don’t see that volume of deals in a quarter. 

In the end, I accepted that I had to start with a smaller number of interviewees and build on it each quarter with a goal of getting to 20. In fact, for our latest report, I combined data from two quarters to get a bigger sample size. 

Another best practice to keep in mind is having your program be not just qualitative but also quantitative. To build the quantitative piece when I started the program, I got together with each functional leader and asked them to set out some KPIs that they wanted to measure. Next, I worked with our consultant to help her integrate those KPIs into the interview. 

The process we set up was to ask the buyer to complete a quick quantitative survey built around our KPIs before the win/loss interview. Then, when the consultant gets on the call with the buyer, she's already seen those ratings and she can adapt her script to really dig into the exceptionally low or high scores to understand the perceptions driving them. 

Another big advantage of having buyers complete a survey in advance is that it allows our consultant to keep her questions really tightly focused. She limits each interview to a maximum of 20 minutes, which is great because that’s a pretty small ask of a potential interviewee.

Running these surveys has also allowed me to create trendlines, which I share in my win/loss reports. Let's say we do 15 interviews in a given quarter, half of them for won deals and half of them for lost deals. With an average overall rating, an average rating for just the wins, and an average rating for just the losses, I can trend how those KPIs are doing over time.

The cross-functional power of win/loss analysis

People tend to think of win/loss programs as being there solely to help sales close more deals successfully. While that’s certainly a major application, it’s only the tip of the iceberg. Win/loss insights can help you drive improvements across virtually every aspect of your business.

For instance, my company has a Net Promoter program, which was previously only used with our existing customer base. I wanted to integrate that into our win/loss program, so we now ask interviewees to tell us on a scale from zero to 10 how likely they are to recommend us to a friend or colleague.

In any given quarter we have roughly a 50/50 mix of net new customers and lost prospects, which makes the answers to this question all the more interesting. Even lost prospects often turn out to be promoters of our company. Although we lost the deal, we really left a great impression, and – you never know – they might come back to us in the future.

As well as asking them for a rating, we ask them, “What would it take for you to provide a higher net promoter rating?” That gives insights into what we could be doing to raise their score even higher.

The hallmarks of a mature win/loss program

Perhaps you already have a win/loss program and you’re wondering how to take it to the next stage of maturity and really maximize the value it provides. What would that look like?

Simply put, a mature win/loss program features regular customer interviews that provide big-picture insights across the organization. Just talking to account teams gives an incomplete internal view that lacks the buyer's perspective.

As I mentioned earlier, when I joined Zuoro, our competitive intelligence function focused purely on providing insights to the sales team. However, I’ve developed and matured our win/loss program to take a more holistic view of the organization. We look at the whole picture – from perceptions of the company to product features to sales interactions – to uncover areas to improve.

For example, we include questions about how customers use references and their influence on decisions. I pass this intel to our customer reference team so they can quantify and boost their impact.

Maturity also means boiling down the data into rich insights instead of just sending raw metrics. These synthesized insights can be used across departments, guiding impactful actions for everyone.

In short, a mature win/loss program continuously captures the voice of the customer, leading to meaningful insights that encompass every aspect of your business. These insights are then delivered to the leaders of each function to drive constant improvement. 

Key takeaways

So, there you have it! Harnessing the voice of the customer in your win/loss analysis isn't just about improving sales; it's about driving meaningful change across your organization. Let's recap some of the main points we've covered:

🔍 Customer insights: The heart of a successful win/loss program lies in listening to what your customers have to say. It’s about getting the full picture, beyond your internal team’s perspective.

🤝 Sales collaboration: Partnering with your sales teams is crucial. It's not about monitoring them; it's about working together to understand customer needs better.

🌱 A holistic approach: A mature program is all about continuous improvement, leveraging insights across all departments, and evolving based on customer feedback.

⚖️ Balancing insights: Striking the right balance between qualitative and quantitative insights is key. Using a combination of surveys and in-depth interviews helps gather a rich, well-rounded understanding of customer experiences.