Below is the introduction chapter from Ryan Sorley’s upcoming book, Blindspots, set for release on April 2nd. For special access to the book, join Ryan’s waitlist here.

Introduction

“You’d think they’d have their shit together given that we’re looking to spend $40 million with them!” 

This CIO was frustrated. And he had every right to be.

“Every time they come to our office for a meeting, they pull up in their fancy SUV, driver and all, and ten people pour out. It’s like a corporate clown car. Am I supposed to be impressed? I’d be more impressed if any one of them could answer my basic questions. Instead, I just get blank stares. What a shit show!”

Do I have your attention? Good. Because I’m telling you my origin story here. This CIO’s rant set me off on an entirely new career path—and eventually led me to write this book.

Let me fill you in on the details. When this epic venting session occurred, I was a vice president at Gartner, one of the top technology research and consulting firms. Chances are you’re familiar with it. This angry CIO worked for a major shoe retailer based out of Boston, not too far from where I live. He was trying to decide between two major enterprise software vendors—we’ll call them Company O and Company S—and he had $40 million to spend.

The CIO thought Company O’s solution was hands-down the better fit. He wanted to go with them. Hell, he was dying to. All he needed before signing the deal were a few answers to some reasonable questions so that the shoemaker’s European HQ would feel comfortable with the deal.

But he couldn’t get those answers. All he got was visit after visit from the clown car.

So, he went with Company S. He didn’t like their solution as much, but they had their act together, they had a clear and concise story, and they provided straightforward answers to his straightforward questions.

As an impartial advisor at Gartner, it wasn’t my job (in fact, it was forbidden) to recommend who this CIO should select. My role was simply to provide information and expertise to help him decide between one tech juggernaut and another.

But, for what it’s worth, I agreed with the CIO on both fronts. Company O was clearly the better fit, but their sales team was clearly failing miserably.

I badly wanted to tell Company O why they were messing up the deal, but as part of our nondisclosure agreement, we couldn’t share any information with or provide any guidance to prospective vendors. Any feedback would have had to come directly from the buyer.

It was like watching a $40 million train wreck. We saw the problem coming miles down the track, but we were powerless to stop it.

Months later, I asked the CIO how Company O had taken the news that they’d lost the deal. “Who the hell knows?” he barked in his thick Boston accent, “I haven’t heard a peep from those bozos since the day I told them they lost the deal! You’d think they’d want to know why!”

It was too late for Company O to salvage this deal, but I was stunned that one of the world’s foremost enterprise software vendors could lose out on a deal of this magnitude and never go back to understand what went wrong. Their own clown show led them to snatch defeat from the clutches of victory. Didn’t at least one of the powers that be want to know that?

There had to be a way for companies like this to connect the dots, to understand what went wrong and why, to learn and grow from the experience.

That was my aha moment.

From that day forward, I vowed to dedicate my entire career to helping all the Company Os of the world learn how to be better…and how to get out of their own way. In this book, I’m going to share all the lessons I’ve learned along my journey.

What’s a Win-Loss Program?

If you’re reading this book, then you’re probably a product marketer who has been put in charge of building or growing a win-loss program within your company, even though you barely know what that means. 

You probably didn’t get a lot of direction on how to do this. No templates. No resources. No best practices. Oh, and no budget either. Just some vague directions on scheduling interviews and offering up some gift cards to respondents as bait.

There’s no sugarcoating it: the odds are stacked against you. But I know product marketers like you. You’re determined to soak up as much information as you can so you can get this win-loss business right. 

As you set out on your hero’s journey, allow me to be your humble guide. Together, we will cover a lot of ground—from program vision to program value. Along the way, I will share the pieces and parts that, when strung together, will enable you to build a program far beyond your expectations.

The journey won’t be easy, but your reward will be great. Not only will you be recognized as the hero that you are, but the knowledge and insight you collect along the way will help arm your company win more deals, keep clients longer, and get a leg up on your competition.

But let’s back up. Why is it that you or your boss suddenly decided now is the time to launch a win-loss program? Could be a lot of reasons:

  • Maybe your company is reeling after a big loss or two to an annoying competitor and you’re hungry for answers beyond what the sales organization can provide.
  • Maybe your sales leaders got grilled during a leadership team meeting on your competition. When they were asked for compelling reasons for their wins and losses…well, let’s just say they were light on meaningful insight, so they were forced to wing it.
  • Maybe your company is in full-on fundraising mode and needs more concrete data so the CEO can impress potential investors with their deep understanding of both the competitive landscape and their buyers.

Whatever the reason, you’ve been handed the job of filling this knowledge void. Somehow, some way, you now have to spin up a best-in-class program that checks all the boxes.

Don’t worry, you’ve got this.

This is your origin story, your hero moment. And it is my honor and privilege to be your guide on this journey.

Why Me?

Who am I, and why have I nominated myself to be your trusty guide? 

I spent over two decades in research, with the majority of that time at Gartner Inc. and Forrester Research, two leading tech-research firms. My job during this time was to help large businesses evaluate enterprise-grade technology solutions.

In that role, I heard some stories. Oh boy did I hear some stories—some even more horrifying than the Case of the Crashing Clown Car. Over and over, I heard executives at multibillion-dollar companies complain about how hard certain vendors were to work with, how their sales team was clueless, how no one at the company seemed to know how their product actually worked. I believed these executives, but I also knew that these vendors, for the most part, were great companies with excellent solutions. They were losing deals due to problems they could easily solve—that is, if they knew those problems existed.

After my Aha! moment, I decided to step away from the world of technology research and niche down in the field of win-loss analysis. It was criminal that organizations like Company O had such massive blindspots in their intelligence infrastructure, and I was determined to eliminate them by helping these companies build mature win-loss programs.

To bring my vision to life, in 2014 I launched DoubleCheck Research. For eight years, DoubleCheck worked with well over a hundred B2B technology and services clients to help them build win-loss programs capable of delivering real, actionable insights in their organizations. In 2022, I sold DoubleCheck to Klue, the leading competitive enablement platform provider and a company I’d long admired and partnered with. Today, I am a Klue Cofounder and Vice President of our win-loss division.

Now part of Klue, we’re combining the power of competitive enablement with the power of win-loss analysis. It’s like combining superpowers (cue nostalgic “wonder twin powers” reference). Every day, I’m grateful to collaborate with brilliant, passionate colleagues who share my enthusiasm for helping B2B teams overcome blindspots, make data-driven decisions, and drive real, measurable change. The passion in our team is downright contagious!

The Journey Begins

In the following chapters, I’ll walk you step by step through the process of standing up a win-loss program in your organization—from securing buy-in, to navigating common challenges and pitfalls, to designing and conducting professional interviews, to making use of all your wonderful win-loss data once you’ve collected it.

Right now, building a win-loss program may seem like just one more to-do on a long list. By the end of this book, you’ll understand that an effective win-loss program is so much more than that, a vessel not only for creating real value within your organization but also for raising your own profile along the way.

If it sounds like a lot, it is. But if you’re ready to embrace your new role and set out on your hero’s journey, come meet me in Chapter 1.