This article is based on a presentation given by Brady at our Customer Success Festival in Austin, 2024.

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Driving customer retention and growth is critical.

One of the most powerful tools I've seen in action is win-loss analysis – a method that can lead to significant improvements in retention, expansion, and overall customer satisfaction. 

In this article, I’ll explore how win-loss analysis can fit into your broader customer success (CS) objectives. I’ll discuss how and when to conduct win-loss analysis within the customer journey, and share some practical tips on how you can get started. 

It doesn’t always have to be a CS initiative, but there are many ways to integrate it into your operations.

The importance of feedback for win-loss analysis

Before diving deeper into win-loss analysis, I want to share a brief story that really hit home for me. 

About a year ago before I joined Clozd, my wife and I went to our favorite restaurant. This visit turned into one of those “I get it –this is why this is important” moments for me. We ordered, but when my meal arrived, the dish didn’t meet expectations.

Now, I don’t do confrontation. My wife, however, is not afraid to speak up. So she politely let the waitress know it wasn’t what she had in mind. The waitress brought out another salad, but it was essentially the same. At this point, I was hoping she wouldn’t say anything more. But my wife raised her hand again, and eventually, the chef himself came out. 

You can imagine my embarrassment when I saw him. I thought, “We’ve offended this poor man.” But I’ll never forget what he said next: “I saw what they brought out, and I am so embarrassed.” He then presented a brand new meal –this time perfectly cooked.

This experience was pivotal for me. It made me realize how often, as leaders, we have a vision of what we think will happen in our go-to-market approach –whether it’s with our sales team, CS team, or any other part of the organization. But reality doesn’t always match that vision. Sometimes, despite our best intentions, we end up with cold Brussels sprouts in our salad, so to speak.

In that moment, my wife was the kind of person who spoke up and gave the restaurant a chance to make things right. But if it had been up to me, I probably wouldn’t have said anything. And that’s where win-loss analysis comes in.

Win-loss analysis is the voice that speaks up, giving your company a chance to make things right. It involves engaging a third party– whether someone within your company or an external partner –to help you understand why you’re winning or losing deals.

The evolving role of post-sale teams

Over the past 24 months, the post-sale landscape has changed significantly. Boards and leadership teams are increasingly looking to post-sale teams to help counteract the effects of economic downturns. 

This shift has likely felt very familiar –you're being asked to do more with less. 

Perhaps you've been told to improve net retention while also managing a team that's 20% smaller, with each rep now responsible for more annual recurring revenue (ARR) per head. It's a classic case of conflicting priorities: you can focus on one, but doing both simultaneously seems nearly impossible.

This is where win-loss analysis becomes crucial. Originally, win-loss analysis was a tool designed for sales teams. Our two co-founders created this product to help sales leaders understand why they were winning or losing new business deals. However, as CS teams have become increasingly involved in revenue-facing conversations, win-loss analysis has naturally evolved into a CS responsibility as well.

Now, many of you are being asked to take ownership of net retention numbers, manage expansion targets, or even hold quotas within your own teams. This means that understanding why you're winning or losing is no longer just a sales issue – it's your issue too. 

Why are some customers churning while others expand? Why do some deals close while others fall through? Let’s break down these problems using win-loss analysis.