How Nav Singh Blends Technical Depth With Emotional Storytelling
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.
From Film to the C-Suite: Matthew Lieberman’s Creative Edge
In This Article Why It Matters Their Path, in Short Big Themes From the Conversation How They Choose the Right Agency Partners What Stood Out The Inside Scoop Why It Matters Matthew Lieberman’s career doesn’t look like the typical path to becoming a CMO—because it isn’t. He started in film, built his business muscles inside PwC, and eventually led one of the largest marketing transformations in professional services. Now he’s stepped into Cooley, a global law firm known for shaping tech and life science giants. His journey matters because it blends creativity, analytics, and a challenger mindset—exactly the mix many CMOs talk about but few actually live. And for agencies, he offers a clear window into how a modern marketing leader thinks, evaluates partners, and chooses who gets a seat at the table. Their Path, in Short Matthew grew up in Los Angeles, surrounded by the energy of the entertainment world. He stayed local for school, dual-majoring in business and film at USC. That mix of creativity and commercial thinking would become a thread through everything that followed. His first job was on the creative side of film—script reading, project development, and shaping stories. He loved it. It taught him how powerful storytelling can be, and how every idea benefits from a creative lens. But he also felt a pull toward the business side of the industry. His studio encouraged him to get his master’s degree, promising him a spot on the business team when he returned. While in grad school, he ended up interviewing at PwC—a firm he only knew as his studio’s auditor. He joined a rotational program that pushed him into an entirely different world: financial modeling, diligence work, and working with major entertainment and media companies. He thought he’d stay two years. He stayed much longer. Eventually, he felt it was time for something new. PwC countered by asking what they could do to keep him. Matthew said marketing looked interesting. At the time, marketing inside professional services was almost entirely events and long-form printed thought leadership. But research—developing insights, shaping points of view, building arguments—spoke to him. So he jumped. That decision set off a long run inside PwC’s marketing organization. He led marketing for entertainment and media. He stepped into roles that felt outside his comfort zone, including leading marketing for the consulting practice. Then he became CMO. During his tenure, the firm went through massive change: new technology, new data capabilities, new buyer expectations, and new competition. Matthew led a full transformation—rebuilding structure, redefining roles, centralizing processes, modernizing the MarTech stack, and aligning marketing with the firm’s business goals. After years of nonstop travel, he relocated full-time to Palm Springs during the pandemic. Later, Cooley approached him. He saw a firm he admired for its culture, its clients, and its entrepreneurial spirit. And he saw another moment ripe for transformation—similar to what he’d lived through at PwC. That sparked the next chapter of his journey. Big Themes From the Conversation One theme that keeps surfacing in Matthew’s story is the courage to run toward something new. When he moved from film to business, and later from consulting to marketing, he did it because he wanted the challenge—not because he was running away from anything. A mentor once asked him, “Are you running from something or to something?” That question still shapes how he leads and how he advises others. Another theme is confidence mixed with humility. Matthew talked openly about imposter syndrome and the value of saying, “I don’t know the answer to this.” He believes leaders should experiment, test, and learn—even when the path isn’t obvious. That mindset helped him push boundaries, question old habits, and rethink long-standing traditions inside large organizations. He also carries a deep belief in the power of creative thinking. His film background didn’t fade once he left Hollywood; it shows up in how he evaluates ideas, how he shapes stories internally, and how he believes modern marketing should look. Creativity, for him, is not a “nice to have”—it’s a business driver. Another throughline is his commitment to team building. One of his mentors taught him the importance of always being present for his team, encouraging new ideas, and bringing people together. Matthew sees leadership as service: giving people clarity, supporting their growth, and creating an environment where they can do their best work. Watch CMO Journey Interview How They Choose the Right Agency Partners When I asked Matthew how he finds agency partners, he didn’t hesitate—relationships matter. Referrals and past experiences still play a major role, both in his PwC years and at Cooley. But that’s only the starting point. At Cooley, he also looks for agencies that can fill specific capability gaps. Search capacity, advanced creative thinking, new technologies—anything that brings in skills his team doesn’t have yet. When an agency reaches out and says, “Here’s something we can do that you may not know about,” that gets his attention. It helps him learn what’s possible and what tools or capabilities he might not be aware of. He also participates in formal RFP processes when needed, often involving procurement teams to build a pool of candidates. But even in a structured process, he avoids a one-size-fits-all approach. Sometimes a hold-co agency with broad resources works. Other times a boutique with deep expertise is the better choice. For Matthew, the answer is almost always a blend. But the biggest differentiator, he says, is personalization. He’s seen major agencies walk in and talk about themselves for an hour. That approach falls flat. The agencies that stand out do the opposite: they show they understand the company, its goals, and its context. They listen. They co-create. They don’t force a rigid work plan—they collaborate on one. Thought leadership also plays a role. Matthew reads constantly, especially on planes. He pays attention to trend-hunting content—even if it’s B2C—because it helps him connect dots in the B2B world. He values case studies and insights on
Jess Alpert’s Unconventional Path to Modern Marketing Leadership
Executive: Jessica “Jess” Alpert, Chief Marketing Officer Company: EPM (Equity Prime Mortgage), Atlanta Industry: Wholesale B2B mortgage lending Company Snapshot: Mid-sized U.S. lender serving independent brokers nationwide Format: CMO Journeys Interview In This Article Why It Matters Their Path, in Short Big Themes From the Conversation How They Choose the Right Agency Partners What Stood Out The Inside Scoop Why It Matters Jessica “Jess” Alpert has taken one of the most unconventional routes into a CMO role you’ll ever hear. She built a fashion brand, ran a creative agency, helped steer major tech marketing, and rebuilt her entire skill set to master data-driven marketing. Her journey is a reminder that high-impact leaders aren’t always shaped by traditional paths. They’re shaped by curiosity, grit, and the willingness to reinvent. For agencies, her perspective offers rare clarity on what truly earns a CMO’s attention. Their Path, in Short Jess began her career by watching people — literally sitting in Nordstrom and observing what customers bought, what they ignored, and how they behaved. That curiosity led her to create an accessories brand built around functional, one-size-fits-all pieces. The business grew fast, expanding into a New York showroom and gaining traction through word of mouth and smart positioning. When she eventually shifted out of fashion, she didn’t go looking for stability. She built her own creative agency, helping brands identify their real pain points and crafting activations that turned heads. One of her most memorable projects was for Faber-Castell, where she created a trade show experience so engaging that attendees clogged the aisle to get a closer look. Her agency work put her on Samsung’s radar, and she soon found herself inside a global tech operation where creativity met data. That’s where she noticed a shift happening. The marketing world wasn’t running on “I feel” anymore. It was running on dashboards and analytics. Instead of resisting it, Jess made one of the boldest moves of her career: she stepped backward in title so she could learn modern marketing from the inside out. She embraced CRM systems, segmentation techniques, analytics, lifecycle thinking — everything that would make her a hybrid leader who could blend creative instinct with measurable results. That hybrid mindset now guides her leadership approach. Big Themes From the Conversation Creativity as a mindset, not a department.Jess doesn’t see creativity as something reserved for copywriters or designers. To her, it shows up in segmentation, user journeys, and every interaction that shapes the customer experience. Curiosity drives everything.She’s always scanning the market, listening for pain points, and asking what people actually need. That instinct powered her early fashion success and still guides her marketing decisions today. Leadership means listening and then moving.Jess listens to her teams, absorbs ideas quickly, and then chooses a direction. She categorizes ideas fast: run with this, refine this, parking lot that. It gives people clarity and builds momentum. She values authenticity over polish.Whether she’s talking about brand tone, internal culture, or agency relationships, she wants work that feels real, not overproduced or overly safe. Execution beats theory.One of her core beliefs: “A brainstorm without execution is just fluff.” It summarizes her entire career philosophy. Watch CMO Journey Interview How They Choose the Right Agency Partners When I asked Jess how she finds and evaluates agency partners, she didn’t hesitate. She values energy, preparation, and genuine connection above everything else. She often discovers agencies at events, where she can meet people face-to-face and get a feel for how they think. She pays attention to the ones who show enthusiasm, bring smart ideas to the table, and genuinely care about the work. If someone lights up when talking about a concept, she notices. If they nitpick retainers and nickel-and-dime hours, she notices that too — and not in a good way. Jess gravitates toward partners who “grow tentacles,” as she put it. Those are the agencies that take a project and expand it with creativity, fresh thinking, and a proactive mindset. They don’t wait to be told what to do. They come with ideas that stretch beyond the assignment. Over time, they integrate so naturally into the team that at an event someone might mistake them for internal staff. Thought leadership also plays a role, but not in the way most agencies expect. Jess doesn’t spend time scanning trade publications. She’s not combing through Ad Age or Adweek looking for clues about agencies. What actually catches her attention is useful, recurring, educational content. She shared an example of an agency that hosts a weekly AI webinar. It was so relevant and so timely that she immediately asked to be added to the list. She loved the idea of a certification tied to it, even envisioning badges people could list on LinkedIn. LinkedIn is her primary discovery platform. Not for resume scanning, but for seeing how agencies talk about their work. She’s drawn to people inside agencies: creative directors, strategists, and team leads who show the process behind a project. She wants to see what the initial pain point was, how the team solved it, and what changed along the way. That transparency tells her more about an agency’s capabilities than any award submission ever could. Awards, for her, are nice, but not persuasive. They give a stamp of approval, sure, but she wants to know what the award was for and whether the thinking behind it was truly fresh. She’s unimpressed by cookie-cutter agencies that do the same work for every client. She wants partners who take risks, think tactically, and deliver ideas no one else is bringing. And when it comes to outreach, she has a clear preference: show up prepared. She dislikes it when agencies use the first meeting to learn about the company. She wants partners who walk in already understanding the business, its customers, and the challenges it faces — not as an agency, but as a consumer. That level of preparation instantly separates the people she wants to work
