Ben Hadley

In the world of enterprise software, where billion-dollar deals are won and lost in boardrooms, Bill McDermott stands apart. He didn't learn to sell by studying case studies at business school. He learned by walking into buildings uninvited, memorizing doormen's children's names, and refusing to be outworked by anyone. This is the story of how a teenage deli owner from Long Island became one of the most successful enterprise software CEOs in history—and why he believes the lost art of human connection is the key to winning in the age of artificial intelligence. The flood came on the day that would change everything. It was 1983, and a young man from Long Island was trying to make it into Manhattan for the most important interview of his life. The streets were underwater. Most people would have turned back. But Bill McDermott had been running a delicatessen since he was a teenager, putting himself through high school and college one sandwich at a time. He had bigger dreams than the deli counter, and those dreams were waiting for him in a Xerox office somewhere in New York City. He made it. Soaking wet, probably, but he made it. The interviewer looked at him and said something that would become a kind of origin story, repeated decades later to podcast hosts and business audiences: "As long as you haven't committed any crimes, you're hired." McDermott hadn't committed any crimes. He got the job. What he walked into was something that no longer exists in American business—a corporation at the absolute peak of its training culture. Xerox in 1983 was what Google or Amazon would become decades later: the place where ambitious young people went to learn how the game was really played. The company was being run by a CEO named David Kearns, who had done something revolutionary. He had looked at what was happening in Japan—at Toyota, at Sony, at the companies that were suddenly dominating global markets—and he had brought their methods home. This was the era of Total Quality Management, a phrase that sounds almost quaint now but represented a complete philosophy of how to build and run a company. Every process was formalized. Every interaction was intentional. Whether you were engineering a product or making a sales call, there was a right way to do it, and Xerox was going to teach you that way. The training program was built on something called SPIN: Situation, Problem, Implication, Needs-Payoff. It was a framework for understanding what a customer actually needed before you ever talked about what you were selling. You started by understanding their situation. You identified their problem. You helped them see the implications of that problem—what it was really costing them, what was at risk. Only then did you talk about how you could help. McDermott graduated number one in his class. But the real prize wasn't the ranking. It was the territory. He got 57th to 59th Street, Fifth Avenue to Park. If you know Manhattan, you know what this means. This is the most beautiful commercial real estate in the world—the kind of neighborhood where you could wear a navy blue suit and a white shirt and a nice tie and feel like you belonged among the masters of the universe. "When I walked down that street," McDermott would later recall, "I was the king of the world." But here's what made him different from every other young salesperson walking those same blocks: he understood that his territory wasn't just a collection of addresses. It was a community. He learned every doorman's name. He learned about their families, their favorite sports teams, their interests. He never missed an opportunity to drop off a cup of coffee on his way up the elevator to the top floor. This was cold calling in its purest form—walking into office building lobbies, unannounced, uninvited, trying to get meetings with buyers who had no idea you were coming. It's a lost art now. You can't even get into most buildings today without ID and someone vouching for you and security letting you through. But in 1983, if you had the nerve and the persistence, you could walk right in. McDermott had both. "The number one rule in sales is it's a numbers game," he explains. "And I was not going to be outworked. So that was not going to happen." He would start at the top floor of a building and work his way all the way down. If somebody moved into the building, he knew about it. If somebody moved out, he knew about it. If a new company was forming, he had his webs around it. He was selling photocopiers, electronic typewriters, fax machines, and the very early laser printers—the mundane machinery of office life that Xerox had turned into a multi-billion dollar empire. The results spoke for themselves. He became number one in the country. Then number one in the world. And with each ranking came more freedom. "Performance is the price of freedom," McDermott says. "I never wanted to sit in internal meetings and have a boss telling me what to do or how to do it. So what I would just tell them is: I'll be number one in the country or number one in the world. Just let me run. Because if I'm inside this building sitting in boring meetings looking at PowerPoints, I'm wasting my day. I need to be loose and on the loose." His managers were happy to oblige. They wanted results, and McDermott delivered results. But something else was happening, something that would define the next phase of his career. Other salespeople started coming to him for advice. They would find him in the morning, sharpening his saw as he put it, or at the end of the day, and they would ask questions. When they struggled, they would ask him to travel with them, to sit in on their calls, to show them how it was done. "This is what makes me happy," McDermott realized. "Making them happy. Helping them be successful is kind of what I was called to do." He got his first management job before he was even twenty-five years old. He interviewed against candidates who were, by any objective measure, more qualified—more experienced, more credentialed, longer tenured. But McDermott walked into that interview with something none of them had: a hundred-day action plan. He laid out in simple terms exactly what he would do in his first hundred days. The other candidates didn't have a well-thought-through action plan. And McDermott wanted it more. He got the job. Seventeen salespeople reporting to him, covering everything from 57th Street to 242nd Street in the Bronx, river to river. Park Avenue to Harlem to the South Bronx. His team was in it all. What he built there became a template he would use for the rest of his career. He took young people straight out of university and shaped them around the market they were serving. He made them look like they belonged. He posted the top three goals of each team member on a wall next to the bell—and these weren't just business goals. They were personal goals. What did you want to achieve as a person? What was the most important motivator inside of you? Then came the philosophy of discretionary effort. Everyone on the team had to identify what they were best at—maybe proposals, maybe closing, maybe financial accounting, maybe writing the best letters and communications. Eighty percent of your job was for you personally. The other twenty percent was for your team. "Nobody gets to fail," McDermott told them. "That was the mantra of the team. And everybody has to make it." He became the youngest corporate officer in Xerox's history. But Xerox, for all its training excellence, was a company that couldn't capitalize on its own innovations. The same research labs that had invented the graphical user interface and the mouse—technologies that would make Apple and Microsoft into the most valuable companies in the world—couldn't translate those breakthroughs into market dominance. McDermott moved on. He went to Gartner, the research and advisory firm, where he learned to see the technology industry from a different angle. Then to Siebel Systems, the customer relationship management pioneer, where he ran the Americas. Then to SAP, the German enterprise software giant, where he would eventually become CEO. At SAP, he orchestrated one of the most consequential acquisitions in enterprise software history: the $8.3 billion purchase of Concur, the expense management company. It was a bet on the cloud at a time when SAP was still primarily an on-premises software company. The deal would prove transformational. But the acquisition that revealed the most about McDermott's philosophy was one that almost didn't happen: Qualtrics. SAP had agreed to acquire Qualtrics, the experience management platform, for $8 billion. Then COVID hit. The world shut down. And suddenly, the economics of the deal looked very different. "I had every reason to walk away from that deal," McDermott recalls. "I had a clause in the contract that would have let me do it. But I had made a promise to Ryan Smith"—Qualtrics' co-founder and CEO—"and I wasn't going to break it." He closed the deal. Qualtrics went on to go public as a separate company, validating the acquisition many times over. But more importantly, McDermott's reputation was intact. He had kept his word when he didn't have to. "The thing about having a word that matters on the street," he explains, "is it's not like when I show up they think I'm there to do some knitting exercise. They know why I'm there. But they also know that if I have something they can hire to do a job, and we can have a common interest in an outcome, and I can move heaven and earth to deliver for them—and I do deliver for them—then we use their time wisely and we did the right thing for them." In 2019, McDermott left SAP to become CEO of ServiceNow, a company that most people outside of enterprise technology had never heard of. When he arrived, ServiceNow had about $3.5 billion in revenue. Today, it has over $10 billion and a market capitalization approaching $200 billion. The pitch he makes to CEOs is deceptively simple. Most large companies, he explains, have been implementing the same enterprise software systems for decades. They have hundreds of different instances of these systems scattered across departments and geographies. Every new administration, every new leader, wants to do things their way. The old stuff never goes away. The mess just gets worse. "You might find this interesting," McDermott says. "Some of these big companies have up to a couple hundred different instances of these systems in each of these silos. Sometimes you'll have an HR system for every thousand employees. And you might say, how can that even happen? Well, think about six decades and every four years you have a new administration that rolls in, and every one of them wants to do it their way." ServiceNow's promise is to cut through this chaos—to provide a single platform that integrates everything, that gives executives a clean pane of glass through which to see their entire operation. In the age of artificial intelligence, when companies are being told they need to deploy AI agents across their organizations, the complexity problem is only getting worse. Those agents are going to have to work with other agents in other departments, just like people have to work with people in other departments. "Who's going to orchestrate this?" McDermott asks. "That's why we designed a business that not only integrates the departments and the people but also the agents." The hardest part of selling ServiceNow, he admits, is getting to the corner office. The CEO is the only person in most organizations who can see across all the silos, who has the authority to simplify rather than add complexity, who is paid to have a broad vision of the whole enterprise without any attachment to the past. "Only the CEO has that clean glass purview to a clean glass platform," McDermott says. "But there is good news. Even if it happens on a departmental level—IT, Finance, HR, Sales, Engineering—you can tie it together with ServiceNow like a Lego set. So you can't make any mistakes. In the end, you get to the same place." The SPIN framework he learned at Xerox four decades ago still guides every conversation. You understand the situation. You identify the problem. You help the customer see the implications. Only then do you talk about the solution. "I had one CEO on the phone yesterday," McDermott recounts. "He said, 'I'm so frustrated with the amount I've put into that system, and it's been several years now, and it's still not done. And then my HR system is so unacceptable because my users don't like using it, and all they do is chronically complain, and I don't have visibility into my people, their training, their onboarding, and how they're actually using the system.' This is the moment when the SPIN framework pays off. The CEO has articulated the situation and the problem. Now McDermott helps him see the implications—the billions at risk, the competitive disadvantage, the employee frustration that compounds year after year. And then, only then, comes the needs-payoff: here's how ServiceNow can fix this, here's what it will look like when it's done, here's how quickly we can make it happen. But there's a catch, and McDermott is emphatic about it: you better deliver. This is the core of his philosophy, the foundation of a reputation built not on talk, but on kept promises. This is the philosophy that has made McDermott one of the most successful enterprise software executives of his generation. It's not about the technology or even the sales methodology. It's about trust. And trust, he believes, can only be built with other people. "The biggest problem that we have in society today is the destruction of time," McDermott argues. "What's happening is people are burned out, but they're burned out for the wrong reasons. It's not where their body is. It's where their mind is. Their mind is stuck inside a device. It gets in there early in the morning and it doesn't get out until almost the next morning. And so the mind isn't resting. But also, where they spend their time is very isolated." COVID, he believes, did lasting damage to the culture of work. It convinced people that they don't live to work, that they work to live. That might sound like wisdom, but McDermott sees it differently. The joy of work—the camaraderie, the shared purpose, the thrill of winning together—is being lost. "I've never met a person yet that loves to talk about their golf score without mentioning the other three people in the foursome," he observes. "We are social people. We need to be with people. We need to celebrate people. We need to celebrate the joy of work again." He remembers making $2.65 an hour. He remembers making twenty bucks for twenty hours of work on New Year's Eve at Amato's Italian restaurant, wearing a tuxedo as a floater. He remembers all of it. But what he remembers most are the moments with other people—the teams he built, the deals he closed, the relationships that lasted decades. "Trust is built in drops and lost in buckets," McDermott says, "and the only place to find it is with your family, your friends, and your colleagues at work. I don't think you're going to find it in the dead space of a device. Because if that's the centerpiece of your world, you're going to have a lot of broken dreams. In the end, the device will still be sitting on the table, and it won't miss you." It's a striking thing to hear from a man who runs one of the world's leading technology companies, a man who talks constantly about artificial intelligence and digital transformation and the future of enterprise software. But maybe that's the point. Maybe the secret to selling technology has never been about the technology at all. Maybe it's about walking into buildings uninvited, learning the doormen's names, and never breaking a promise.