I have spent over 10 years leading sales organizations across Latin America at SAP, Salesforce, and now ServiceNow. AI is bigger than any technology change I have experienced, and the old rules no longer apply. Most of my day is spent talking to CEOs, CIOs, and operational leaders, answering the same question: “How can we use AI for our business?”
I’m starting to see a pattern. Technical barriers are real, including data disconnection, legacy system fragmentation, and integration complexity. These are not small problems and no amount of leadership will make them go away, but they are solvable. Once a company has the right infrastructure foundation in place, the difference between those making real progress and those still waiting to make progress mostly comes down to the people at the top and the culture they’ve built around them. Movers have decided that imperfect action is better than complete inaction and have built teams that can learn while doing.
Below are leadership lessons that I keep coming back to as I work in an industry that changes faster than any playbook can keep up with.
simplicity is strategy
My favorite word is “simplicity,” and that applies here more than anywhere else. One of the biggest mistakes leaders make with AI is trying to transform everything at once. Instead, start by identifying one or two use cases where AI can provide immediate value and expand from there.
The simpler the strategy, the more likely it is to be implemented. I’ve seen talented teams freeze under sophisticated roadmaps with 17 workstreams. I’ve seen similarly talented people accelerate when leaders say, “Here’s what we’re going to solve this quarter, and here’s what winning looks like.”
For our team, it started with how sellers prepare for conversations with customers. We built an AI-powered coaching experience on Anthropic Claude that combines real-time research and account context. Preparation that used to take days can now be completed in an hour. Sellers come into the conversation more informed and free to focus on tasks that require real human judgment, such as building trust, understanding situations, and solving real problems.
This one use case changed the conversation within our company. AI has ceased to be an abstract imperative and has begun to become something that employees reach for because it improves their work. Lesson: Don’t start out ambitious. Start with what works, make it undeniable, and build momentum from there.
AI is creating a tremendous amount of noise about what is possible, what will happen, and what competitors are doing. In such an environment, the leader’s job is not to add to the environment, but to carve it out.
If AI doesn’t lead by example, it will lose trust.
Even if you have a working use case, adoption will not happen automatically.
When I started incorporating AI-generated insights into my team’s conversations and using it to prepare for customer meetings, pressure-test account strategies, and move faster through tasks that previously took hours, my team took notice and saw that AI could benefit the way I work.
This is a typical challenge that is not talked about enough in the AI context. Leaders who delegate without modeling adoption are telling their teams that AI is for execution, not leadership. The executives I see driving real AI momentum within their organizations are people who are genuinely curious, are visibly learning, and want to be actively involved in the early stages of understanding AI. That attitude gives your team permission to do the same.
People are scared, that’s your most important leadership challenge
What is not often said out loud is that many people are afraid. They have 20 years of expertise and have always done things a certain way, but now they see the rise of AI and wonder if their experience still matters. That fear doesn’t necessarily manifest as resistance. In some cases, it manifests itself as waiting, over-engineering, or pursuing the perfect implementation before taking action.
Last year I was asked to speak to a senior team about leadership. I have decided not to share what I have learned. I shared what I was still working on: my struggles, my questions, and my commitment to growth, even when it was uncomfortable. Empathetic leadership is needed now more than ever, and the ability to be vulnerable is a strength. If a leader has to be the smartest person in the room, the room stops contributing. When people fear that their mistakes will define them, they pursue perfection instead of progress. In the age of AI, there is no time for perfection. The train is moving. The question is whether teams are building the conditions to ride it.
In practice, this means creating an environment where people are truly supported to experiment, where “we don’t know this yet” is fully accepted as an answer, and where learning is rewarded with results. That means understanding what your employees are moving around outside of the office. Not because it’s your business, but because it shapes what they look like. Once that foundation is in place, everything else – technology, execution, and results – will be able to hit the ground running.
Building that environment only matters if you are actually willing to trust it. A few months ago, my daughter’s soccer team was losing badly and they needed me on the sideline. At that exact moment, an important meeting with the region’s largest customer appeared on my calendar and was about to begin. My team ran the conference without me and had full ownership of the conference. I didn’t have to save it because I had spent months preparing it, trusting them, and making sure it was safe to operate without me in the room. Instinct is what tries to take control when things go wrong. It may solve the moment, but it permanently weakens the team. And this is exactly the wrong instinct for AI transformation, as the pace of change means teams need to continually learn and adapt, rather than waiting for instructions from the top.
Leading an organization in an AI company in 2026 means operating at the intersection of limitless ambition and true complexity. Latin America is at a tipping point. As companies move from experimenting with AI to implementing it, the organizations that seize the moment will be those with leaders who act decisively, lead with integrity, and build the human conditions for their teams to succeed.
Enrique Upton He is ServiceNow’s vice president and general manager for North Latin America.
