Win-Loss 101: Kicking off your first win-loss analysis project | Part 1 of 6

Nate Bagley

You can do everything right and still lose

Clark is a sales leader who’s obsessed with “best practices.” 

He equips his sales team with all the best software, tools, and training to help them personalize their prospecting, run textbook discovery calls, conduct mind-blowing demos, and empower buyers to make a solid internal business case for his company’s products.

He uses his call-recording software to coach reps on an individual basis, and he always keeps an eye on their pipeline so he can make sure they’re set up to hit quota in coming quarters.

And yet … 

… despite doing all the “right” things, the results have been slipping. His team isn’t hitting pipeline goals, closing deals, or making quota as consistently as they used to.

So Clark starts to wonder: “Are we doing something wrong? Is there something off with our product? Is the marketplace changing? Or are we losing because of reasons outside our control, like the economy?” 

The truth about sales is that you can do all the right things … and still lose. It’s the same way with your health. You can eat nutritious foods, get lots of sleep, work out regularly … and still get cancer.

In sales, best practices aren’t enough anymore. If you want to succeed in the current economic climate, you need a tool that can help you diagnose and treat invisible problems in your business that can lead to “revenue cancer.”

Using buyer intelligence to diagnose revenue problems

You know that the path to confidently hitting quota requires more than simply increasing expectations for your sales reps and SDRs. You need to know exactly why you’re winning and losing deals—and you need to have the power to change and improve anything in the business that could result in more closed-won deals.

Just like a doctor might use an X-ray or MRI machine to examine your body for problems you can’t see on the surface, a good business leader must rely on their buyers’ first-hand accounts in order to discover and diagnose unseen revenue problems. 

When Craig Clark, CMO at Riskalyze, began his company’s win-loss analysis program, he didn’t fully comprehend all the ways it would empower him to change their business.

“[Win-loss analysis has] been quite transformational. I think it’s a true statement that we had many assumptions about why we win and why we lose, and that a good many of those assumptions have been definitively proven to be false. We’ve made product packaging changes, pricing changes, GTM messaging changes, positioning changes, and churn-reduction changes. Anecdotally, we’re sporting a 50+% win rate, up from the 30% range in the post-Clozd era. I can't say that is causal, but it certainly has not hurt.”

Because they haven’t kept up with the evolution of win-loss analysis technology, most revenue leaders are constantly increasing the pressure to drive more pipeline. Technology-enabled win-loss analysis programs help you win more deals by giving you the power to make changes to anything that’s not working for your buyers, including pricing, packaging, product, marketing messaging, customer onboarding, and more. 

The old-school way of doing win-loss analysis consisted of pulling a CRM report of closed-lost deals, then having a meeting to discuss why you *think* you lost one or two of your “key” deals. Then … nothing would really change. No new processes. No improved win rate. No help hitting revenue targets. 

This outdated type of win-loss analysis wasn’t valuable because it rarely involved hearing from the most important person in the sales process—the buyer. 

Everything changed, however, when third-party win-loss analysis providers like Clozd came along.

“60% of sales reps don't understand how they won or lost a deal. Clozd provides a platform to dig deeper into your products and services by creating a safe space between seller and buyer. … Third-party interviews are crucial for me to form a competitive intelligence program. Clozd allows me to view insights clients typically don't share with sales reps.”

Jordan Barsness | Competitive Intelligence at PitchBook Data

The solutions to your revenue problems aren’t hidden in a CRM report. They can only be found in one obvious yet often-overlooked place: the experiences of your buyers.

If you want a competitive edge, you must conduct in-depth interviews directly with your buyers to identify the positive and negative Decision Drivers (factors that influenced your buyer’s decision). 

The most important insights must then be shared with relevant key stakeholders throughout your business, so you can make the necessary changes to win more deals, build better products, and stop leaving money on the table.

In the Win-Loss 101 series, you’ll learn how to get a win-loss analysis program off the ground, so you can start collecting buyer feedback that can result in improvements across your entire business, and most importantly, more revenue. 

How to start a win-loss analysis program

There are six simple steps that help you create and run a successful win-loss analysis program:

  1. Identify a revenue problem to investigate
  2. Develop an interview template to guide you in your search for answers
  3. Reach out to your buyers
  4. Interview—and survey—your buyers
  5. Analyze your data for Decision Drivers
  6. Report your findings to enact change

The most mature win-loss analysis programs continuously provide leaders with important insights that remove the guesswork and uncertainty from the decision-making process.

Our goal is to help you get to that point. 

Whether you’re running your program in-house, or hiring a third party, every program starts the same way. The rest of this post will focus on helping you take that first step to getting a win-loss analysis program off the ground: Identifying a revenue problem.

How to identify a revenue problem

The biggest hurdle most leaders face when kicking off a win-loss analysis program for the first time is simply knowing where to start. 

We recommend that you begin by identifying a problem to investigate in one of the following five areas:

  • Competitor: Why do we keep losing to the same company?
  • Deal Size: Why do we consistently struggle to close enterprise deals?
  • Churn: Why are our supposedly “happy” customers leaving?
  • Product: Why are we seeing such low adoption of our new feature?
  • Geography: Why is our AMEA team underperforming?
“Your CRM tells you what the problem is. Then, win-loss analysis tells you why it’s happening.”
Cam England | “The Win-Loss Guy”

Your CRM, your executive team, or even your sales reps will have insights into which of these problems are having the biggest impact on revenue. Compile a list of the most pressing issues, and then take it to the leaders of your company to see which of those issues matter most to them (and why).

This accomplishes two goals:

  1. It helps you prioritize problems in order of importance and impact
  2. It helps you get buy-in from key stakeholders to investigate and solve these problems

Common mistakes to avoid when choosing a revenue problem

As you choose a specific revenue issue to focus your win-loss analysis program on, make sure you avoid these two common mistakes:

  1. Choosing a topic that’s too broad
  2. Overcomplicating the process

Choosing a topic that’s too broad

As Clozd consulting team lead Cameron Turnbow said in this lesson of Win-Loss 101, “Don’t try to boil the ocean.”

If you immediately interview two churned customers, five closed-lost enterprise deals in AMEA, and three closed-won mid-market deals in the Americas, you won’t get enough relevant data to validate your findings. That means you won’t have anything meaningful to take back to your leadership team to influence change.

Instead, narrow your focus to one problem, and then focus on talking to customers who can shine a light on both what you’re already doing well and how you can do better.

Overcomplicating the process

It’s easy to convince yourself that you need to have a bunch of email automations and processes in place before you start reaching out to buyers.

Don’t get stuck in a cycle of analysis paralysis!

Your first win-loss project shouldn’t require multiple months of planning. Follow the process in this series, and within about a month you should have the groundwork in place to unearth meaningful buyer insights that have a direct impact on win rates and revenue goals—without the program totally consuming your life.

Each part of the series has one simple homework assignment. Do the homework, and you’ll see results.

Your first assignment

Your first assignment to help you get your win-loss analysis program up and running is to choose a revenue problem you want to solve. Run some CRM reports and talk to your sales leaders to see if there are any issues they’d like you to explore.

The revenue problem choose to investigate should fall into one of the five categories we mentioned above (competitor, deal size, churn, product, or geography).

Once you’ve locked in on a problem, you’re ready to proceed to the next lesson.

This article is the first in a six-part series to help you launch your first win-loss analysis project—so you can experience the value of getting feedback directly from your buyers. Click below to check out the rest of the series.

Part 2 | Part 3 | Part 4 | Part 5 | Part 6

For a personalized Clozd demo, sign up here.

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Win-Loss 101: Kicking off your first win-loss analysis project | Part 1 of 6

Nate Bagley
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You can do everything right and still lose

Clark is a sales leader who’s obsessed with “best practices.” 

He equips his sales team with all the best software, tools, and training to help them personalize their prospecting, run textbook discovery calls, conduct mind-blowing demos, and empower buyers to make a solid internal business case for his company’s products.

He uses his call-recording software to coach reps on an individual basis, and he always keeps an eye on their pipeline so he can make sure they’re set up to hit quota in coming quarters.

And yet … 

… despite doing all the “right” things, the results have been slipping. His team isn’t hitting pipeline goals, closing deals, or making quota as consistently as they used to.

So Clark starts to wonder: “Are we doing something wrong? Is there something off with our product? Is the marketplace changing? Or are we losing because of reasons outside our control, like the economy?” 

The truth about sales is that you can do all the right things … and still lose. It’s the same way with your health. You can eat nutritious foods, get lots of sleep, work out regularly … and still get cancer.

In sales, best practices aren’t enough anymore. If you want to succeed in the current economic climate, you need a tool that can help you diagnose and treat invisible problems in your business that can lead to “revenue cancer.”

Using buyer intelligence to diagnose revenue problems

You know that the path to confidently hitting quota requires more than simply increasing expectations for your sales reps and SDRs. You need to know exactly why you’re winning and losing deals—and you need to have the power to change and improve anything in the business that could result in more closed-won deals.

Just like a doctor might use an X-ray or MRI machine to examine your body for problems you can’t see on the surface, a good business leader must rely on their buyers’ first-hand accounts in order to discover and diagnose unseen revenue problems. 

When Craig Clark, CMO at Riskalyze, began his company’s win-loss analysis program, he didn’t fully comprehend all the ways it would empower him to change their business.

“[Win-loss analysis has] been quite transformational. I think it’s a true statement that we had many assumptions about why we win and why we lose, and that a good many of those assumptions have been definitively proven to be false. We’ve made product packaging changes, pricing changes, GTM messaging changes, positioning changes, and churn-reduction changes. Anecdotally, we’re sporting a 50+% win rate, up from the 30% range in the post-Clozd era. I can't say that is causal, but it certainly has not hurt.”

Because they haven’t kept up with the evolution of win-loss analysis technology, most revenue leaders are constantly increasing the pressure to drive more pipeline. Technology-enabled win-loss analysis programs help you win more deals by giving you the power to make changes to anything that’s not working for your buyers, including pricing, packaging, product, marketing messaging, customer onboarding, and more. 

The old-school way of doing win-loss analysis consisted of pulling a CRM report of closed-lost deals, then having a meeting to discuss why you *think* you lost one or two of your “key” deals. Then … nothing would really change. No new processes. No improved win rate. No help hitting revenue targets. 

This outdated type of win-loss analysis wasn’t valuable because it rarely involved hearing from the most important person in the sales process—the buyer. 

Everything changed, however, when third-party win-loss analysis providers like Clozd came along.

“60% of sales reps don't understand how they won or lost a deal. Clozd provides a platform to dig deeper into your products and services by creating a safe space between seller and buyer. … Third-party interviews are crucial for me to form a competitive intelligence program. Clozd allows me to view insights clients typically don't share with sales reps.”

Jordan Barsness | Competitive Intelligence at PitchBook Data

The solutions to your revenue problems aren’t hidden in a CRM report. They can only be found in one obvious yet often-overlooked place: the experiences of your buyers.

If you want a competitive edge, you must conduct in-depth interviews directly with your buyers to identify the positive and negative Decision Drivers (factors that influenced your buyer’s decision). 

The most important insights must then be shared with relevant key stakeholders throughout your business, so you can make the necessary changes to win more deals, build better products, and stop leaving money on the table.

In the Win-Loss 101 series, you’ll learn how to get a win-loss analysis program off the ground, so you can start collecting buyer feedback that can result in improvements across your entire business, and most importantly, more revenue. 

How to start a win-loss analysis program

There are six simple steps that help you create and run a successful win-loss analysis program:

  1. Identify a revenue problem to investigate
  2. Develop an interview template to guide you in your search for answers
  3. Reach out to your buyers
  4. Interview—and survey—your buyers
  5. Analyze your data for Decision Drivers
  6. Report your findings to enact change

The most mature win-loss analysis programs continuously provide leaders with important insights that remove the guesswork and uncertainty from the decision-making process.

Our goal is to help you get to that point. 

Whether you’re running your program in-house, or hiring a third party, every program starts the same way. The rest of this post will focus on helping you take that first step to getting a win-loss analysis program off the ground: Identifying a revenue problem.

How to identify a revenue problem

The biggest hurdle most leaders face when kicking off a win-loss analysis program for the first time is simply knowing where to start. 

We recommend that you begin by identifying a problem to investigate in one of the following five areas:

  • Competitor: Why do we keep losing to the same company?
  • Deal Size: Why do we consistently struggle to close enterprise deals?
  • Churn: Why are our supposedly “happy” customers leaving?
  • Product: Why are we seeing such low adoption of our new feature?
  • Geography: Why is our AMEA team underperforming?
“Your CRM tells you what the problem is. Then, win-loss analysis tells you why it’s happening.”
Cam England | “The Win-Loss Guy”

Your CRM, your executive team, or even your sales reps will have insights into which of these problems are having the biggest impact on revenue. Compile a list of the most pressing issues, and then take it to the leaders of your company to see which of those issues matter most to them (and why).

This accomplishes two goals:

  1. It helps you prioritize problems in order of importance and impact
  2. It helps you get buy-in from key stakeholders to investigate and solve these problems

Common mistakes to avoid when choosing a revenue problem

As you choose a specific revenue issue to focus your win-loss analysis program on, make sure you avoid these two common mistakes:

  1. Choosing a topic that’s too broad
  2. Overcomplicating the process

Choosing a topic that’s too broad

As Clozd consulting team lead Cameron Turnbow said in this lesson of Win-Loss 101, “Don’t try to boil the ocean.”

If you immediately interview two churned customers, five closed-lost enterprise deals in AMEA, and three closed-won mid-market deals in the Americas, you won’t get enough relevant data to validate your findings. That means you won’t have anything meaningful to take back to your leadership team to influence change.

Instead, narrow your focus to one problem, and then focus on talking to customers who can shine a light on both what you’re already doing well and how you can do better.

Overcomplicating the process

It’s easy to convince yourself that you need to have a bunch of email automations and processes in place before you start reaching out to buyers.

Don’t get stuck in a cycle of analysis paralysis!

Your first win-loss project shouldn’t require multiple months of planning. Follow the process in this series, and within about a month you should have the groundwork in place to unearth meaningful buyer insights that have a direct impact on win rates and revenue goals—without the program totally consuming your life.

Each part of the series has one simple homework assignment. Do the homework, and you’ll see results.

Your first assignment

Your first assignment to help you get your win-loss analysis program up and running is to choose a revenue problem you want to solve. Run some CRM reports and talk to your sales leaders to see if there are any issues they’d like you to explore.

The revenue problem choose to investigate should fall into one of the five categories we mentioned above (competitor, deal size, churn, product, or geography).

Once you’ve locked in on a problem, you’re ready to proceed to the next lesson.

This article is the first in a six-part series to help you launch your first win-loss analysis project—so you can experience the value of getting feedback directly from your buyers. Click below to check out the rest of the series.

Part 2 | Part 3 | Part 4 | Part 5 | Part 6

For a personalized Clozd demo, sign up here.

Clozd gave us insights into the 'why' we were winning deals."

Ike Nwabah

  | VP of Marketing

Outstanding means of understanding why you win and lose."

Tripp R.

  |  Global Competitive Insights Manager

Depth of knowledge we could never achieve on our own."

Gary C.

  |  VP of Product Marketing