Why It Matters
Nav Singh’s path to the CMO seat at Eightfold AI is anything but typical. His story blends engineering, product leadership, and a deep curiosity about how people work and what they need. He’s someone who made bold pivots, embraced uncertainty, and kept following the spark of what interested him. For agencies, his journey matters because it reveals what impresses him, how he thinks about partners, and what truly earns attention in a fast-changing AI world.
Their Path, in Short
Nav began his career expecting to build a future in consulting. Coming out of his MBA, he imagined himself rising through Deloitte and becoming a tech partner. But when projects dried up early in his career, he had to pivot fast. That shift took him into a startup and eventually into Oracle—where someone pointed out that the work he was doing was actually product management. Until that moment, he didn’t even know what product management was.
That discovery kicked off a 15-year run building products, meeting customers, shaping roadmaps, and becoming deeply fluent in how technology works. But another turning point came while he was at a small startup, wearing multiple hats because there wasn’t a marketing team. When he found himself creating emails and updating the website, he noticed something important: he loved connecting with customers emotionally, not just technically.
That insight pulled him into marketing. He turned down several product roles to take a marketing position at Palo Alto Networks—an unusual move for someone with his background. But it paid off. Over the next decade, he blended product depth with storytelling to help shape narratives that moved people and drove business impact. Today at Eightfold AI, he’s drawing on everything he learned to sharpen a clear, human-centered story around what the company does and where the world of work is heading.
Big Themes From the Conversation
A major theme in Nav’s journey is curiosity. He has a habit of stepping toward what he doesn’t know rather than away from it. He chose product without understanding the field. Later, he chose marketing because something about it felt creatively alive. He treats curiosity not as a trait but as a path forward.
Another theme is his belief in listening. When he stepped into his CMO role, he didn’t build strategies based on decks, templates, or AI-generated plans. He sat down with about 40 people to understand what customers were saying, what teams had experienced, and what wasn’t written anywhere. For him, the best answers come from people, not algorithms.
A third theme is staying grounded in customer truth. Nav has seen how easy it is for teams to fall in love with their own product. He knows what it feels like to get fixated on what you’ve built instead of what customers actually need. He’s committed to making sure storytelling and decisions stay rooted in real customer insight.
And running through his leadership philosophy is encouragement. He keeps a simple rule in mind: give far more positive feedback than corrective feedback. In his experience, teams do their best work when they feel seen, supported, and challenged in the right balance.
Watch CMO Journeys Interview
How They Choose the Right Agency Partners
When I asked Nav how he finds great agency partners, his answer showed just how open he is to new ideas—and how practical he is about time. Some agencies come from past experience. At Palo Alto Networks, he had a front-row seat to world-class partners across social, web, and creative. That gives him a baseline of what good looks like.
He also taps his network when he needs recommendations. But he doesn’t stop there. Nav actually scans his LinkedIn messages, not because he has time to reply to most of them, but because he doesn’t want to miss someone with a creative spark. What he doesn’t respond to are the “Do you have five minutes?” messages. Those go nowhere.
What works is clarity. He wants agencies to tell him what they do, explain the value, and show an idea—preferably in a short video. A two-minute Loom with a clear explanation can get his attention faster than any pitch deck. He wants to see how someone thinks, not just what they claim.
At events, he browses booths, watches demos, and talks to people, but he doesn’t go to conferences specifically to shop for agencies. Inspiration happens in conversations or in unexpected moments.
And one of the most revealing parts of his philosophy is how he views awards. They don’t move him. Awards look in the rearview mirror, and he’s far more focused on who is thinking about the future. He’s drawn to agencies that bring ideas about where marketing is headed and how teams will work alongside AI—not just what they’ve done before. If you can show new ways to scale content, use technology wisely, or experiment with fresh approaches, you have his attention.
What Stood Out
One moment that really stood out was when Nav talked about the hero’s journey. He believes the customer—not the company—is the hero. The company is the guide. That mindset echoes through how he listens, how he shapes stories, and how he keeps teams from getting lost in their own product.
Another revealing moment was how he keeps his own creativity sharp. He pulls inspiration from solo road trips, conversations with his kids, time in the wilderness, and watching an eclectic mix of YouTube content. He treats creativity as something that needs space, input, and curiosity—not a rigid process.
Inside Scoop
This article focuses on the journey, the leadership philosophy, and how this CMO works with agency partners. To access the exclusive analysis, including priorities, initiatives, and opportunities, become a Next Big Win Pro member.
