At Sierra Ventures’ 20th CXO Summit, ServiceNow CEO Bill McDermott sat down with Tim Guleri for a candid conversation that moved fast and stayed concrete. It tracked his path from a Long Island deli to leading global software companies, and then delved into how to scale AI that actually delivers.
Start with hustle, stay with hustle
When a first-grade teacher told Bill’s parents, “He’s a good boy, but don’t expect too much of him,” he made an early decision that no one would ever outwork him. At sixteen, he bought a deli on credit and turned it into a community hub. He delivered groceries to seniors who didn’t want to leave home, extended credit to blue-collar families who paid on Fridays, and found a way to attract high schoolers from a nearby 7-Eleven by adding a video game room. Since he couldn’t afford the machines, he struck a deal to split the quarters with the supplier. Within 90 days, the games had paid for the store. The lesson: know your customer, remove friction, and create reasons for people to choose you.
Create your shot
At 21, the Xerox interview was not a meeting; it was a turning point. When the hiring leader said HR would follow up, Bill pushed for a decision and left with the job. He calls it a fight for his life, not bravado, but clarity. The lesson: conviction changes odds. You still need competence, but you win the moment by wanting it more and making that visible.
Set a standard the whole team can see
As a young sales manager, he set a public target: every rep would make the President’s Club. He mapped people to neighborhoods where they could win, made goals visible on the wall, and required everyone to share craft. Monday mornings started early, and Friday closed with accountability. No one was left behind. The lesson: raise the bar, make it public, coach daily, celebrate progress.
Performance is the price of freedom
Bill dislikes bureaucracy that dilutes customer time. His deal with HQ was simple: if his team hit the number, they earned the right to be “on the loose” with customers. That freedom pushed speed without letting standards slip. The lesson: speed and standards are not in conflict when performance is clear and measured.
Build trust before you need it
In his first 100 days at ServiceNow, he met employees and top customers worldwide. When COVID hit, those relationships carried the company through a sprint of releases that helped workplaces reopen and supply chains operate. He repeats a simple line: trust is built in drops and lost in buckets. The lesson: do the meetings early, before the storm.
AI that works crosses the org chart
Bill takes a practical view of AI. Point solutions trapped in silos rarely deliver results because real business processes cut across teams and systems. His answer is a single, secure, agentic platform that connects functions, integrates models and data, and measures success by tangible outcomes people can feel. When the NHL hesitated to start another proof of concept, ServiceNow instead built and deployed a live system in just two weeks. Satisfaction soared, adoption followed, and the results spoke for themselves. The lesson: integrate first, then automate—and prove value in weeks, not quarters.
From proof of concept to proof of value
Executives are tired of pilots that never scale. They want fewer platforms, deeper partners, and fast proof. Bill’s advice to startups was direct: choose a beachhead, prove the outcome, and strengthen your channel through real partnerships. Good inventions die without distribution. Great go-to-market turns sparks into engines.
A platform lens on enterprise AI
Bill describes what he calls east-to-west AI. It is one pane of glass that crosses IT, HR, customer operations, and engineering. It connects to any cloud, any model, any data source. It respects security and choice by supporting zero-copy access to data when moving it is not feasible. Internally, ServiceNow runs the company on a single AI-driven portal. Employees see what they need, and agents handle the bulk of service requests. In HR the current ratio is about one agent to hundreds of employees, with headroom to double. The lesson: platforms win when they reduce switches, collapse handoffs, and make outcomes observable.
Operating cadence is a strategy
Bill gets up early for quiet thinking, then anchors the day around customers. He hires leaders to lead, answers messages in minutes, and removes roadblocks so processes move fast. He will join his executives’ sessions when invited, but he does not hover. The standard stays high. The tactics live with the person closest to the work. The lesson: a CEO’s calendar sends a stronger signal than any memo.
Talent philosophy
Hire nines and tens. If you bring in an eight or seven, plan the coaching from day one and move quickly on truth. He prefers to fire people up rather than fire them. When it still does not fit, decide cleanly. Do not move mediocrity around the org. Onboarding matters as much as hiring. People should meet the company the website promised. Training must be personal, measurable, and modern, including AI skills. The lesson: standards, clarity, and humane speed can coexist.
Resilience as a teachable edge
Coming back from a severe injury deepened his empathy and sharpened his purpose. Vulnerability made him more accessible. The lesson: resilience is not only endurance, it is connection. People run through walls for leaders who see them.
The market and the mandate
Bill frames AI as both a driver of growth and an enabler of efficiency. The headline is growth first, with meaningful cost takeout following. He also calls out a sober truth: most transformation projects fail on integration, not intent. AI will not fix that on its own. Architecture, data, and processes must align. The end state he describes flips the org chart. The customer sits at the top. Cross-functional work becomes the default. Agents and people operate together across the full journey from discovery to service. The lesson: the companies that align architecture to outcomes will set the pace.
Advice to founders in the room
Pick a real problem in a real process. Show time to value in days or weeks. Land with a partner when reach is the bottleneck. Keep your brand trustworthy, promise less than you deliver, and measure the outcome in the numbers your buyer already watches. Pilots are not a business model. Proof is.
Bill’s playbook stays consistent. 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 remember the line he repeats often: performance is the price of freedom.
