At Sierra Ventures’ 20th CXO Summit, ServiceNow Chairman & CEO Bill McDermott joined Tim Guleri for a fast-paced, story-driven conversation. From his Long Island deli days to leading global software companies, McDermott shared the values and practices that shaped his leadership and how those same principles now guide his approach to building the next generation of enterprise AI.

Winning Traits: Hustle, Conviction, and Resilience That Stick

Bill’s story begins with relentless hustle. After a teacher told his parents not to expect much, he decided no one would ever outwork him. At sixteen, he bought a deli on credit, paid it off within a year, and turned it into a local hub featuring arcade machines. The lesson: know your customer, remove friction, and create reasons for people to choose you.

At 21, his Xerox interview became a defining moment. When told HR would follow up, he refused to leave without a yes and got the job. His mindset: conviction wins when competence and preparation back it up.

Years later, recovering from a serious injury deepened his empathy and renewed his drive. True resilience, he says, is not just endurance but connection. People rally behind leaders who show vulnerability and purpose.

Lessons in Leadership: Standards Over Titles

Early in his career, Bill McDermott set an unconventional goal: every sales rep on his team would make President’s Club. He made goals visible, coached daily, and celebrated progress. “Performance is the price of freedom,” he told them. Deliver results and you earn autonomy.

His leadership style centers on trust and clarity. He meets people early, builds relationships before the storm, and insists on speed paired with high standards. He avoids bureaucracy and empowers his teams to act quickly while staying accountable. His schedule, built around customers and quiet reflection, reinforces what he calls leadership through presence.

Hiring and Culture: Fire People Up, Don’t Fire Them

Bill McDermott’s hiring philosophy is simple: aim for nines and tens. If you hire an eight or a seven, invest immediately in coaching, but do not move mediocrity around. Onboarding and training must match the culture promised. He believes great companies are built by leaders who inspire, not intimidate.

He also warns against leaders who over-control. Attention to detail is valuable, but over-approval kills creativity. The best leaders set the standard, trust their people, and remove roadblocks. As he puts it, a CEO’s calendar sends a stronger signal than any memo.

The Future of Enterprise AI: From Proof of Concept to Proof of Value

Bill McDermott’s outlook on AI is grounded in outcomes, not hype. He argues that tools in silos fail because real business processes cross teams. ServiceNow’s model, which he calls north-to-south and east-to-west, connects any model, any cloud, and any data source across the enterprise, from IT and HR to customer operations and engineering.

He illustrated it with a real example. When the NHL hesitated to start another proof of concept, ServiceNow built and deployed a live system in two weeks. Satisfaction soared. The takeaway: integrate first, then automate, and prove value in weeks, not quarters.

Executives, he says, are done with pilots that never scale. They want fewer platforms, deeper partners, and tangible ROI. His advice to startups: focus on real problems, prove outcomes fast, and partner strategically. Pilots are not a business model. Proof is.

Looking ahead, McDermott believes AI will force companies to reorganize around the customer. The org chart will flip, cross-functional work will dominate, and systems must connect seamlessly. The companies that align architecture to outcomes will win.

His Personal Playbook

Do the hard work early. Set visible standards. Remove friction for customers and teams. Measure value honestly. Move fast because you have earned the right to. And never forget the line he repeats often: performance is the price of freedom.