Jamie Richardson on Curiosity, Clarity, and Leading White Castle
Executive: Jamie Richardson, Chief Marketing OfficerCompany: White CastleIndustry: Quick-service restaurant and frozen retail foodCompany Snapshot: A family-owned brand with both restaurant and retail businesses, known for its long history and distinct identityFormat: CMO Journeys Interview Why It Matters Jamie Richardson’s story matters because it does not move in a straight line. He began in agency life, moved inside one brand, stepped across functions that many marketers never touch, and returned to marketing with a broader view of how a business works. That makes his perspective especially useful. It is also useful for agencies. Richardson talks about partnerships with seriousness, clarity, and high standards. He is not looking for surface-level chemistry. He is looking for shared effort, cultural fit, and work that can actually change the trajectory of a brand. Their Path, in Short Richardson likes to begin with a story that explains a lot about how he sees work. To help pay for college, he sold fire extinguishers door-to-door. It meant talking to strangers, making a clear case, and learning how to keep going after rejection. It is a memorable detail, but it also feels like an early lesson in resilience. He grew up in a small town in Michigan, ran cross country and track, and found his way into marketing early. His first major chapter was at J. Walter Thompson in a management training program. He loved the pace and the variety. Agency life gave him exposure to different categories, different clients, and different ways of solving problems. That path led him to White Castle. He had worked on the brand from the agency side, then moved inside the company. What drew him in was not just the role. It was the culture. He described White Castle as a place where the values felt real, not decorative. That mattered. His career inside the business expanded well beyond marketing. He moved through corporate relations, shareholder relations, government affairs, public relations, and philanthropy before returning to marketing leadership. Each stop added something new. Corporate relations widened his understanding of reputation. Shareholder relations taught him how important communication becomes when people want to feel included. Government affairs gave him a completely different lens. Marketing, he said, is offense. Government relations is defense. That range shaped how he leads. He does not talk about marketing as one isolated department. He talks about it as part of a larger system, one connected to culture, trust, communication, and long-term stewardship. His story is not really about switching functions. It is about learning that brand strength comes from seeing the whole business more clearly. Big Themes From the Conversation One big theme is discomfort. Richardson said he hopes people feel a little out of their depth every day. That is where growth happens. Not in chaos, but in stretch. He seems to believe that if the work feels too easy for too long, something important has gone flat. Another theme is curiosity. He talked about reading widely, sharing ideas, and building habits that let people learn across disciplines. He spoke warmly about White Castle’s business book clubs, which is telling. He likes ideas, but he seems even more interested in what happens when ideas get discussed in a room with different kinds of thinkers. He also values clarity. In leadership, he wants people to know the goal, know the expectation, and know how success will be measured. That is not because structure is comforting. It is because clear work moves faster. When people understand the job, they can do better work together. And that word together matters to him. He even pauses on the meaning of collaboration itself: co-labor, to work together. For Richardson, collaboration is not just getting along. It is bringing different strengths into the same room, being honest about what is and is not working, and using that honesty to improve the outcome. Watch Or Listen CMO Journey Interview How They Choose the Right Agency Partners When I asked Richardson about agency relationships, he did not begin with capabilities. He began with philosophy. White Castle, he said, wants to be the best client and the best partner an agency has. That framing says a lot. He is not interested in a lopsided relationship where one side simply extracts value from the other. He wants real partnership. That shapes how he evaluates agencies. He talked about the selection process as something that deserves care. Cultural alignment matters. Shared commitment matters. He wants the decision taken seriously because the goal is not a quick assignment. It is a relationship that can help the brand grow. He notices effort. He notices care. One story stood out. During the review process, GSD&M transformed the outside of its office to look like White Castle, then carried that experience inside. Richardson did not describe that as empty showmanship. To him, it signaled attention to detail and real investment. It showed that the agency understood the brand deeply enough to build an experience around it. He also values honesty and practicality. He wants partners who understand the realities of the business, who can move quickly, and who know how to help a smaller brand make a bigger impact. He appreciates teams that immerse themselves fast, write clearly, and come in with sharp thinking instead of vague enthusiasm. What he seems to want most is alignment. He thinks in terms of shared strengths. What should the internal team own? What should a partner bring? Where can each side create the most value? His approach is not rigid or ideological. It is grounded in efficiency, clarity, and mutual respect. What Stood Out What stood out most was Richardson’s mix of seriousness and play. He can talk about reputation, collaboration, and business pressure with real weight, then describe White Castle at night as “Night Castle” and call the sign “a beacon of hope on the highway of life.” That sense of humor feels important. It suggests a leader who can carry responsibility without losing personality. Another revealing detail is that he still
RFPs Are Usually the End of the Story — Not the Beginning
Problem / Context Many agencies think they are early because they got invited into the RFP. But by the time an RFP becomes visible, a lot has already happened. Budget conversations have started. Internal priorities have shifted. Leadership has aligned around a problem. In some cases, agencies are already being discussed quietly behind the scenes. That means most firms are entering the process after the market has already moved. This is one of the biggest reasons modern new business feels harder than it used to. Teams are competing at the point where everyone else can see the opportunity too. The Signal One of the strongest signals in modern agency business development is organizational change. That could be: A new CMO A new product launch A funding round A merger or acquisition A shift in leadership structure Hiring activity tied to growth or transformation These moments usually happen before an agency search becomes public. We see this repeatedly across executive conversations, CMO interviews, job postings, and market announcements. The signal is not the opportunity itself. The signal is evidence that priorities may be changing. We explore this idea in more depth in our “How to Find and Win the Companies Hiring Agencies — Before the RFP” webinar, including real examples of the signals agencies should be paying attention to. Why It Matters Most agency outreach still happens without context. A generic capabilities email. A cold pitch. A random check-in. The problem is not just that buyers ignore these messages. The bigger issue is that they show no understanding of what the company is actually going through. Signals create relevance. If a company just hired a new marketing leader, there may be pressure to evaluate positioning, performance, agency relationships, customer acquisition, or internal capabilities. That does not guarantee a project. But it gives you a much smarter lens for how to show up. The Mistake Most Teams Make Most teams treat signals as permission to sell. They see a funding announcement and immediately send a pitch. They see a new CMO and rush into outbound. That approach usually fails because the timing may be wrong, the context may be incomplete, and the outreach often feels transactional. Signals are not a shortcut to sales. They are guidance. The goal is not to pounce. The goal is to better understand what may be changing inside the organization. The Smarter Move The smarter move is to use signals to guide relationship-building behavior. That could mean: Sharing relevant research Sending thoughtful commentary tied to the company’s direction Inviting leaders into a peer roundtable Connecting around an industry event Staying visible through valuable content AI can help surface these signals faster. But judgment still matters. The advantage is not simply knowing that something changed. The advantage is understanding what the change might mean. How to Use This The agencies building the strongest pipelines today are not waiting for opportunities to become obvious. They are paying attention earlier. Not to sell faster. But to understand where companies may be heading before everyone else shows up. That creates better conversations, stronger positioning, and more trust over time. Because the best business development is not built on volume. It is built on relevance, timing, and relationships.
Inside Sunil Frida’s Human Approach to Leading at Scale
Executive: Sunil Frida, Chief Marketing OfficerCompany: ZscalerIndustry: Cloud securityCompany Snapshot: Zscaler helps companies replace legacy network architecture with a cloud-based Zero Trust model.Format: CMO Journeys Interview Why It Matters Sunil Frida’s story is not a straight climb up a neat corporate ladder. It is a story about seeing the world early, learning discipline young, and then discovering that great technology only matters if people can actually understand it. That idea runs through everything he says. It also makes his perspective useful for agencies. Because when Frida talks about marketing, he is not talking about polish for polish’s sake. He is talking about clarity, trust, and the hard work of making something complex feel simple and useful. Their Path, in Short Frida grew up in Singapore in what he describes as a middle-class neighborhood, with a sports journalist father and a schoolteacher mother. His parents did something that clearly stayed with him: they stretched what they had to show their family the world. He still tells the story with a laugh. His father was willing to make five flight stops just to save fifty dollars. The trip took forever. It was worth it. That early life sounds grounded and ordinary in the best way. Close friends. School bus rides. Sports. A family that cared about doing well in school and making the most of what was possible. Frida does not present himself as some childhood prodigy. He says he was not the best student or the worst student. But he worked hard. That theme comes up again and again. Then came military service in Singapore, which he describes as life-changing. It was not just about training. It was where he started to understand leadership as real care. That experience, he says, shaped how he thought about leading others. His next turn came in Australia, where he studied engineering after what sounds like a very human, very unplanned moment. He had missed deadlines. A door happened to be open. A professor happened to be there. A spot happened to open. Frida tells the story almost like a shrug, but it lands as something bigger: sometimes a career starts because one door is open on a Friday afternoon. From there, he moved into the tech world and then product management. But the big shift came later, at AWS, when he realized the job was not only to understand the technology. It was to explain it. He saw senior leaders spend days refining language so a complex idea could be understood in simple English. That changed his view of marketing. The breakthrough was not about “speeds and feeds.” It was about positioning, messaging, and making the value real to another human being. Big Themes From the Conversation One theme that kept surfacing was simplicity. Frida comes from technical environments, but he does not romanticize complexity. He almost argues the opposite. If you cannot explain what you are building in plain language, then the brilliance of the product does not matter very much. That belief feels central to how he leads. Another theme is discipline. You can hear it in the way he describes school, the military, and later his working style. He likes focus. He likes priorities. He likes stripping things down to what matters. Even when he jokes, there is a through-line: energy is limited, time is limited, so use both well. There is also a real warmth in how he talks about people. He was pleasantly surprised by how driven and mission-oriented the culture at Zscaler felt from the inside. He talks about joy at work without sounding forced or performative. For him, joy is not extra. It is part of what makes good work possible. And then there is curiosity. Frida sounds like a person who wants to understand how things work all the way down. Not just the headline. Not just the pitch. The actual mechanics. That curiosity shows up in his questions, in his stories, and in the way he describes building teams and solving problems. Watch Or Listen CMO Journey Interview How They Choose the Right Agency Partners When I asked how he thinks about agency partners, Frida did not give a vague speech about collaboration. He got specific fast. First, he starts with scope. What is the work? What are the big buckets that need to get done? What can the internal team do well on its own, and where does outside support actually make sense? That sounds obvious, but he treats it like a discipline, not a slogan. He also draws a pretty clear line around certain work. Product marketing, in his view, belongs close to the product and the market. He describes it as part art, part science, and he does not sound eager to hand that over. Other areas, like media, advertising support, social, and reach extension, are different. Those are places where outside partners can help the company scale. But here is where it gets interesting: Frida is not looking for agencies to impress him with volume. He is looking for them to make sense. He says a lot of outreach lands on his LinkedIn and in his inbox. The agencies that stand out are the ones that can explain, in simple English, how they would help his product and story scale. Not a flood of data. Not a giant pile of industry talk. Clarity. He also wants depth. Frida says he asks a lot of questions and likes to get into the weeds. He comes from product and product marketing. So when someone pitches him, he wants to know the why behind it. Why would this work? Why this approach? Why this message? He is not looking to be read the news. He is looking for someone who understands the product, the customer, and the connection between the two. That creates a useful lesson for agencies. Frida seems to respond less to flash and more to translation. Can you take something technical and make it intelligible? Can you show that
Why AI Is Creating a Massive Opportunity for Agencies
I recently sat down with Scott Brinker, a leading voice in marketing technology, to discuss how AI is changing opportunities for agencies. Brinker has spent over two decades in marketing technology, leading strategy at HubSpot, founding a SaaS company, advising startups, and publishing chiefmartec for 80,000+ industry leaders. He’s best known for creating the Marketing Technology Landscape annual report. He’s seen every major wave of change in how marketing gets done. That’s what made his perspective on AI stand out. While much of the conversation has focused on disruption and replacement, Brinker sees something else emerging — something that could drive significant demand for agencies. AI Isn’t Just Disrupting. It’s Overwhelming. One of the first things Brinker pointed to is the speed of change. Unlike past technology shifts that took years, AI is compressing transformation into months or even less. That compression is putting pressure on organizations. Companies are being forced to rethink their technology, customer engagement models, and how work gets done internally. Most aren’t set up to manage that level of change. As Brinker put it, “overwhelming is an understatement.” This shift in behavior is critical: instead of trying to figure everything out internally, many companies are now looking outward for guidance. For agencies, that shifts the role. It’s less about executing predefined work and more about helping clients determine what they should be doing in the first place. The Structural Advantage Agencies Have In Brinker’s view, agencies are uniquely positioned in this environment because of how they accumulate experience. A brand may face a transformation once. An agency does it repeatedly across clients. Each engagement provides lessons that can be reused. He describes this as a form of arbitrage. Companies get one version of the transformation. Agencies get many. In a moment where there is no clear playbook, that repetition becomes valuable. It allows agencies to move faster, avoid common pitfalls, and bring a level of pattern recognition that most internal teams don’t yet have. A Delivery Model Under Pressure Yet, as agencies find themselves in this evolving role, the way they deliver work is also beginning to change. Historically, much of an agency’s value came from execution: the production, coordination, and manual work needed for campaigns. Pricing often relied on time and resources. AI is starting to absorb a meaningful portion of that execution layer. As that happens, the traditional time-and-materials model becomes harder to defend. Not because the work itself is less valuable, but because the inputs have changed. “The time and materials basis of this has become irrelevant,” Brinker said. What clients still want is the outcome. Strategy, creativity, and orchestration remain central, but the way those are packaged and priced is shifting toward impact rather than effort. Why This Isn’t a Simple Race to the Bottom One concern that comes up frequently in conversations about AI is commoditization. If the tools are widely accessible, does everything become interchangeable? Brinker’s perspective is more nuanced. While AI may standardize parts of execution, companies aren’t hiring agencies for sameness. They’re hiring them to differentiate. That puts more weight on imagination, judgment, and the ability to translate ideas into something that actually works within a business. Not all strategy is equal. As AI improves, some structured analysis is easy to replicate. The defensible work is original thinking, clear positioning, and tying ideas to real-world needs. A Shift Beneath the Surface: From Applications to Infrastructure Another change Brinker highlighted is happening at the technology level. For years, marketing has been built around packaged applications—tools with fixed capabilities that companies assemble into stacks. That model is evolving as AI makes it easier to build custom workflows, tools, and agents on top of broader platforms. In this environment, technology becomes less about individual applications and more about infrastructure. For agencies, this creates new opportunities. They help design how systems are built, connected, and used, extending work beyond campaigns into internal marketing operations. Multiple Transformations Happening at Once Part of what makes this moment so complex is that it isn’t just one shift. It’s several things happening at once. Brinker pointed to three in particular: the transformation of technology and data infrastructure, the transformation of buyer behavior, and the transformation of how work gets done inside organizations. Each of these would be significant on its own. Together, they create a level of change that most companies struggle to manage internally. That complexity is what’s driving demand—not just for execution, but for guidance. The Gap Between Strategy and Execution Is Shrinking AI is also compressing the distance between strategy and execution. In the past, there was a clear separation between the two. Strategy was developed first, and execution followed over weeks or months. That gap is now shrinking. What once took months can now be built, tested, and iterated in days or even hours. That creates a different operating model, one where thinking and doing are much more closely connected. For agencies, the ability to move fluidly between strategy and execution becomes increasingly important. Why Smaller Agencies May See New Opportunities One of the more interesting implications of this shift is what it means for smaller agencies. Historically, larger agencies benefited from scale: more people, more resources, and broader capabilities. AI begins to level parts of that equation by making advanced capabilities more accessible to smaller teams. That said, the advantage isn’t absolute. While the capability gap may narrow, other factors, such as visibility, reputation, and access to enterprise clients, remain significant. For many smaller agencies, the challenge isn’t whether they can deliver the work, but whether they can consistently get in the room to compete for it. The Real Challenge: Managing Change Despite all of these opportunities, most organizations are still behind. Not because the technology isn’t available, but because adapting to it is difficult. Even companies making decisions in response to AI often haven’t fully figured out how they will operate differently as a result. That points to a broader issue. The challenge isn’t just adopting AI. It’s managing
Adam Shpiro on Reinvention, Growth, and Leading Across Change
Executive: Adam Shpiro, Chief Marketing OfficerCompany: SBSIndustry: Financial technology softwareCompany Snapshot: SBS provides software platforms for banks, lenders, and payment systems.Format: CMO Journeys Interview Why It Matters Adam Shpiro’s path to the CMO seat did not follow a straight line, and that is what makes it worth studying. He moved through engineering, consulting, agriculture, venture investing, banking, and commercial strategy before taking over marketing. Each stop gave him a different lens on leadership, growth, and decision-making. For agencies, his perspective is useful because he does not talk about marketing as a silo. He talks about it as part of the whole business. Their Path, in Short Adam said that at 18, he would not have predicted this career. He saw himself as a math-and-physics person and studied mechanical engineering at the University of Bristol. But during that time, he realized something important: engineering was not the right long-term fit. So he pivoted. He moved into management consulting, then took a far less expected turn when an opportunity came up through a family office investment in Malawi. He volunteered to go and joined an agricultural business there. What began with one department grew into broader leadership, and eventually he was running the business. That chapter clearly shaped him. He described it as life-changing. He was young, far from home, and suddenly exposed to the realities of leading a raw, unsophisticated business. He also got pulled into looking at investments across countries and industries. It was hands-on, fast, and demanding. When he returned to Israel, he expected to move into startups. Instead, he landed in early-stage venture capital. That role taught him something else: he had built strong practical business experience, but he wanted a deeper business foundation. That led him to business school, then to JPMorgan, where he worked in a leadership development program and later in corporate development on the retail banking side. From there, he joined a digital banking startup and got a closer look at what a high-growth environment really feels like. Later, at SBS, he first came in through a go-to-market and commercial strategy lens. When he was asked to lead marketing, he said his reaction was simple: I have never actually worked in marketing before. But that was part of the logic. The role called for someone who could connect marketing to the broader business. Big Themes From the Conversation One idea came through again and again: Adam is comfortable when the path is not fully mapped. He does not talk about growth as a clean sequence of planned moves. He talks about trying things, learning quickly, shutting down what is not working, and moving forward again. For him, progress seems to come from motion, not perfection. That carries into how he leads. He said quality still matters, but now it is quality and speed. That is a meaningful distinction. He is not arguing for sloppiness. He is arguing against hesitation. He would rather build a team that can move and learn than one that gets stuck protecting itself from every possible mistake. He also returned to a lesson from an earlier boss in Africa. The advice stayed with him because it was simple and human: life is a long road, so do not sprint through it. Follow your heart. Do something you love, because you will probably be much better at that than the things you do not love. It is the kind of advice that sounds soft until you realize how much of his career it explains. Another strong theme was connectedness. Adam does not see marketing as a group of separate channels or specialties. He sees interdependence. Content affects product marketing. Product marketing affects digital. Digital affects field. That is why he values a real leadership team structure inside marketing. He wants people to understand not only their own lane, but also how the lanes connect. Watch Or Listen CMO Journey Interview How They Choose the Right Agency Partners When I asked Adam about agencies, his answer was less about flash and more about substance. He spoke about working with outside partners in areas like content, media, and events. Content matters because SBS is full of experts, and the company wants to give those people a voice. Media matters when reach matters. Events matter because bringing customers and the wider ecosystem together matters. But his real test for agencies starts earlier. It starts with whether they understand the objective. Then whether they understand the KPI. Then whether they can connect their work to the business outcome that matters. He used a phrase from Hebrew that translates roughly to having “a big head,” meaning someone sees the wider purpose, not just the immediate task. That idea says a lot about what he wants from partners. He does not want someone who simply delivers the asset they were asked for. He wants someone who understands why the asset exists in the first place. He also made a clear distinction between service and partnership. In content, for example, he said there is still a difference between AI-generated work and work created by professionals who understand the industry. At the same time, he expects professionals to use the best tools available. The point is not to protect an old model. The point is to produce work that helps the business hit its goals. That standard applies more broadly, too. “You asked for X, here it is” is not enough. Adam wants agencies that go further. Agencies that stay proactive. Agencies that do not get complacent after the first win. Agencies that keep checking whether the work is still aligned with the outcome. That is where credibility lives for him. Not in noise. Not in polish alone. In usefulness, business understanding, and the ability to keep creating value over time. What Stood Out What stood out most was Adam’s lack of ego about his own story. He has worked across sectors, functions, and leadership roles, but he tells that story with unusual honesty. He is quick
What New CEOs Reveal About Where Marketing Dollars Go Next
Problem / Context Most agencies look for one signal when trying to find new business: A new CMO. It makes sense. CMOs are the buyer. They control marketing budgets. They hire agencies. But by the time a new CMO is in place, something important has already happened. The decision to change. And that decision usually starts somewhere else. The Signal A new CEO. Not every time. Not in every company. But when a company brings in a new CEO (especially from the outside), it signals something deeper. The business needs to change. Growth has stalled. Strategy needs to shift. Pressure is building. And when that happens, marketing is almost always part of the reset. Why It Matters A new CEO does not just inherit a strategy. They question it. In the first 90 days, they are asking: What markets should we be in? What is not working? Where can we grow faster? That creates movement. Sometimes it leads to a new CMO.Sometimes it puts pressure on the current one.Almost always, it creates demand for new thinking. And that is where agencies come in. Not because they are needed eventually. Because they are needed now — before the plan is locked. The Mistake Most Teams Make They treat CEO changes like a one-time trigger. Send an email. Maybe connect on LinkedIn. Then move on. Or worse, they ignore the CEO entirely and wait for the CMO change to happen. Both miss the point. A CEO hire is not a moment. It is a window. And that window can last 6–12 months as strategy, budget, and teams evolve. The Smarter Move Use the CEO change to guide how you show up — not how fast you sell. Start with context: What was this CEO hired to do? What is their background: growth, product, operations? What industries are they coming from? Then qualify the opportunity: Is this a category that uses agencies? Is there likely to be marketing investment? Are there other signals: hiring, repositioning, expansion? From there, engage the buying committee. Not just the CMO. The CFO is thinking about spend.The CRO is thinking about pipeline.The COO is thinking about execution. Each sees the change differently. So your perspective should reflect that. How to Use This Treat CEO changes as a signal to stay close, not jump in. Follow the company.Watch how the story unfolds.Layer in insight over time. That might look like: Sharing relevant research Offering perspective based on similar transitions Inviting them into conversations with peers The goal is not to catch them at the perfect moment. It is to be present when the decision takes shape. Because by the time an RFP appears, the direction is already set. And the agencies that win are usually the ones who were there earlier — helping make sense of the change. The bottom line is this: CMOs may sign the deal. But CEOs often create the reason the deal exists in the first place.
Marie Lee’s Journey From Insider to Challenger
Executive: Marie Lee, Chief Marketing Officer Company: Princess Cruises Industry: Cruise travel and vacation experiences Company Snapshot: An iconic cruise brand with deep heritage (including “The Love Boat”), focused on delivering an active, elevated vacation experience built around discovery. Format: CMO Journeys Interview Why It Matters Marie Lee has built a career by following one simple rule: learn the business from the inside out, then use that knowledge to move people. She spent years inside an experience-driven giant, then took a leap into a brand that needed fresh momentum. In this conversation, she doesn’t just talk about marketing—she talks about the guest, the team, and the kind of agency partnership that actually works. For agencies, her viewpoint is a reminder that trust and precision matter as much as creativity. Their Path, in Short Marie describes her career as a series of chapters built on variety—and the discipline to turn that variety into a clear understanding of how a business runs. She started in travel-industry sales, then moved into marketing. Along the way, she worked in international markets, learned how regional differences change what “good marketing” looks like, and took on roles that weren’t purely creative or purely analytical—but demanded both. She shifted into areas like merchandise strategy and broader lines-of-business strategy, which later connected to product development work. That was a turning point for her, because it forced a deeper question: if the “product” is the experience, how do you design everything around the guest? From there, she moved into direct marketing, and that evolved into customer engagement work that included media and marketing. Eventually, she led strategy planning and integration in the media space and worked closely with media agencies at the executive level. Then came a pivot that required a leap of faith. She had built a long career inside one company, to the point where she called herself a “lifer.” But she also felt stagnant—like she was asking, “Is this it?” When Princess Cruises approached her, she said she could see a clear path forward: a different media approach that could help grow the business. She took the jump, led media strategy, expanded into partnerships and social, and later moved into the Chief Marketing Officer role—carrying the same thread through every chapter: connect the consumer to the business, and move revenue forward. Big Themes From the Conversation One theme kept showing up: start with the guest. Marie’s belief is straightforward—“bet in the guest” and “know your consumer.” In her world, marketing isn’t separate from experience. It’s the front door to it. You attract people by meeting them where they are, and you keep them by delivering something they want to talk about. Another theme: growth comes from trust—especially trust in people. Marie doesn’t frame leadership as personal heroics. She talks about picking people you can trust, developing them, and “giving them wings.” In her telling, the best outcomes don’t come from one person having the best idea. They come from building a team that can run fast with good judgment. She also talks about momentum. When she describes stepping into bigger roles, she keeps returning to impact: the need to deliver, the need to move. But she pairs that with something else—building over time. She speaks in “two truths”: the reality of short-term results and the responsibility of long-term brand building. She doesn’t treat those as competing goals. She treats them as the job. A final theme is her comfort with iteration. When she talks about AI, she doesn’t romanticize it. She says you can’t write a big strategic plan and expect to follow it. You have to try things, learn, and be iterative. But she also adds a practical warning: none of it matters if your foundation isn’t solid. If the data sources aren’t connected, you’re building on sand. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked Marie what a collaborative agency relationship looks like, she didn’t describe a vendor. She described a teammate. Her core philosophy is simple: an agency should be an extension of the internal team. And if you want an agency to make the best recommendations, you have to share what you know. That means context—your biggest challenges, where you’re headed, what you’re trying to accomplish as a brand and as a business. In her view, an agency can’t be helpful from the outside looking in. They have to be brought into the real work. But she’s also clear that “nice” isn’t the goal. Candor is. She talks about the need to say, “This isn’t going to work,” and to explain the why behind it. It’s not criticism for sport. It’s the honest feedback loop that keeps teams from drifting. She sees that kind of openness as the only way to navigate a media landscape that keeps changing. She also believes chemistry is not a soft factor—it’s the multiplier. When she talks about what she fears most when hiring an agency, she doesn’t start with capability. She starts with the risk of being pulled down the wrong path, or never finding the spark that allows both sides to grow together. In her words, agencies often have great talent. But talent only turns into “one plus one equals three” when there’s trust and chemistry. And she wants something else that many agencies claim, but fewer deliver: courage. She explicitly says she doesn’t want a “yes man.” She wants an agency that challenges her ideas, debates, and brings a point of view—especially in an environment where AI is changing the landscape rapidly. She wants partners she can use as a sounding board: “I’ve been given this opportunity—what do you think? How would you move forward?” Marie also describes how she sources new capabilities in a very grounded way. Often, she starts with existing partners first—asking whether they can provide what’s needed, or whether someone else within their broader network can. She also mentions using a corporate sourcing team to identify potential partners. The point is not
What Agencies Still Don’t Understand About Today’s CMO
As part of the upcoming CMO Lab at POSSIBLE (April 27–29 in Miami Beach), I sat down with Nadine Dietz, who is leading the initiative and has spent years working closely with CMOs across the industry through her work at Virtuosi League, Adweek, and Marketers That Matter. The conversation quickly moved beyond the event itself and into something more telling. On paper, the CMO role hasn’t changed. The mandate is still growth, customer, and brand. But in practice, the role is operating in a completely different environment than it was even a few years ago. That gap between what the role looks like and how it actually operates is where much of the friction is today. And it’s also where many agencies are falling behind. The Shift Isn’t Marketing. It’s Enterprise. One of the biggest changes Nadine pointed to is where CMOs are actually spending their time. It’s less about managing marketing execution and more about navigating the enterprise. CMOs today are expected to operate across the C-suite by aligning teams, influencing decisions, and helping define what growth actually means across the organization. That kind of alignment work isn’t always visible, but it’s now central to the role. A major driver of this is AI. Not because of the tools themselves, but because AI decisions don’t live in one function. They impact operations, finance, product, and HR, forcing CMOs into conversations that go well beyond marketing. They’re no longer just running a function. They’re helping shape the system in which the function operates. Why Good Ideas Aren’t Enough Anymore This is where the gap between CMOs and agencies starts to show up. From Nadine’s perspective, the issue isn’t that agencies aren’t capable. It’s that many are still approaching problems in ways that don’t reflect the reality CMOs are operating in. Ideas alone don’t move things forward the way they used to. Strategy can look great on paper, but it breaks down when it doesn’t fit into the broader organization, doesn’t align with other priorities, or can’t scale across teams and systems. In practice, that breakdown shows up in subtle ways. An agency might bring a strong campaign idea, but executing it requires new data flows, coordination across product and sales, or approvals that take months to navigate. The idea isn’t wrong. It’s just not deployable in that environment. And that’s often where momentum dies. CMOs aren’t just asking, “Is this a good idea?”They’re asking, “Will this actually work here?” A Model That’s Starting to Break There’s also a more fundamental shift happening in how work gets done. The traditional agency model: long timelines, structured campaigns, and clearly defined scopes, is under pressure. The pace of change, combined with the expectation for real-time responsiveness, is forcing companies to rethink how they operate. That shift is showing up in team structure as well. More work is being broken into tasks rather than roles. More talent is being brought in on a fractional basis. And more capabilities that once lived outside the organization are being pulled in-house, often supported by AI. For agencies, this creates a different kind of challenge. It’s not just about doing the work better. It’s about fitting into a system that is actively being rebuilt. What the Best CMOs Are Doing Differently What’s becoming clear is that the CMOs gaining traction aren’t just focused on marketing outcomes. They’re focused on alignment. They’re thinking about how decisions are made across the organization, how teams work together, and how to build systems that actually support growth—not just campaigns that aim to drive it. It’s a more complex job than it was even a few years ago. And it requires a different kind of partner. Where Agencies Need to Rethink Their Approach If there’s one theme that came through clearly, it’s this: agencies need a deeper understanding of the environment in which their clients operate. That starts with empathy, but not in the abstract. In practice, it looks like shifting the conversation. Instead of leading with ideas, the most effective agencies are spending more time diagnosing constraints: How do decisions actually get made inside this organization? What would prevent this from working? Where are the bottlenecks likely to be? It also means pressure-testing ideas before presenting them. Not just “here’s what we’d do,” but “here’s how this would realistically get implemented given your current structure.” Because from the CMO’s perspective, time is limited and the margin for error is small. Every initiative has to fit within a broader set of priorities that agencies don’t always see. In many cases, the agencies that stand out aren’t the ones with the boldest ideas. They’re the ones whose ideas actually work inside the system. The Part No One Talks About Toward the end of the conversation, the focus shifted from strategy to something less discussed. People. Teams are being asked to do more with less. Roles are evolving faster than people can adapt. And there’s a constant level of pressure that sits underneath all of it. In Nadine’s view, the mental health impact across the industry is significant and growing. And yet, most organizations are still focused on chasing the next opportunity rather than investing in the people who deliver it. That disconnect matters. Because in a moment like this, the strength of the team is what determines whether any strategy actually works. Why Spaces Like the CMO Lab Are Emerging That shift is also what led to the creation of the CMO Lab at POSSIBLE. The idea isn’t to add more content to an already crowded conference schedule. It’s to create space for CMOs to step back, compare notes, and work through challenges that don’t yet have clear answers. Because that’s the reality right now. There isn’t a clear playbook for navigating AI transformation, organizational alignment, and evolving expectations simultaneously. Most CMOs are figuring it out as they go. And increasingly, the most valuable insights aren’t coming from the
Esi Eggleston Bracey on Leadership, Change, and Doing You
Executive: Esi Eggleston Bracey, Former CMO Company: Unilever Industry: Consumer Goods Company Snapshot: Global consumer brands company Format: CMO Journeys Interview Why It Matters Esi Eggleston Bracey did not set out to become a marketer. She thought she was headed toward a very different future. But once she found brand building, she found the thing that matched how her mind works: solve problems, understand people, create value. That is what makes her journey worth studying. It is not just a story about rising through big companies. It is a story about trusting your own instincts, growing through discomfort, and staying human while leading at scale. For agencies, her view is especially useful because she is clear about where outside partners matter most. That is also why her perspective will resonate well beyond this conversation, including at POSSIBLE, where she will help lead a broader industry discussion about where marketing and agency value go next. Their Path, in Short Esi grew up in Chicago and describes herself as a kid who loved numbers. Math was her favorite subject. She was curious, active, and, in her words, precocious. Her mother was a lawyer and civil rights activist. Her father was a math teacher. Marketing was not on her radar. She calls herself an “accidental executive,” and that feels like the right place to start. She did not map out a career in business or brand management. What pulled her in was something simpler: she loved solving problems, and she loved people. Once she started at Procter & Gamble, the fit clicked. She realized marketing let her connect insight, creativity, and business in one place. Some of her earliest lessons came from small moments that turned into big ones. As a young brand assistant on Comet Cleanser, she looked at the tear tape on the package and saw more than packaging. She asked whether it could help build awareness for a new product. It could. That simple idea became a major driver of awareness. For her, it was an early lesson in what happens when focus, creativity, and analysis meet. That pattern kept showing up. She talked about helping develop Febreze by connecting a real human tension to a business need. She talked about CoverGirl and listening to people who did not feel seen by narrow beauty standards. Across those stories, her approach stayed the same: understand what people need, then build something that answers it in a way that helps the business grow. Her career also stretched her personally. Moving to Geneva while expecting her second child was one of those moments. Leaving the culture of P&G and stepping into new environments was another. She does not tell those stories like they were easy. She tells them as moments of uncertainty. Then she tells you what she did next: she jumped in. Big Themes From the Conversation The biggest theme in her story is growth through challenge. Esi said every challenge is an opportunity for growth. That is not just a leadership line for her. It is how she has moved through both professional and personal change. Scary moments, in her telling, often became the most transformative ones. Another theme is individuality. Early in her career, she realized she had been trying to conform. She thought success meant studying the environment and matching what she saw. Over time, she learned the opposite. One of her clearest principles is, “Do you. It’s your superpower.” She says it simply, but it carries weight because it came from experience. She also talks about energy in a way that feels practical and personal. She said she manages energy, not just time. Time is limited. Energy can be renewed. That tells you a lot about how she thinks. She is not interested only in output. She is interested in what allows people to keep growing, leading, and showing up fully. And throughout the conversation, she keeps coming back to people. Not just consumers in a narrow sense, but whole people with tensions, needs, and desires. Even when she talks about building brands, she talks about helping people first. That is part of what makes her leadership style feel warm instead of abstract. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked her how she thinks about agencies, she started by zooming out. The fundamentals of brand building, she said, have not changed. You still have to understand people, create desire, and turn that desire into commerce through reach, engagement, and conversion. What has changed is the ecosystem around that work: the tools, the channels, the speed, the expectations. That matters because it shapes how she sees agency value. In her experience, the most irreplaceable thing agencies bring is ideas and creativity. Not just campaigns. Not just ads. Ideas that can travel. Ideas that connect to culture. Ideas strong enough to live across different voices and formats. That is where she sees real outside value. She was equally clear about what marketers need to own. In her view, the marketer has to be the integrator. The ecosystem is too complex to outsource the full picture. Data, commerce, media, innovation, and creative thinking all have to connect, and the brand owner has to hold that together. Agencies can support that work with media strategy, planning, execution, insights, and intelligence. But support is different from ownership. That is also why she pushes back on the simple idea that AI means cutting agency spend. She does believe there is waste in the system. She does believe productivity should improve. But she separates that from the bigger question. The better question, she says, is this: what creates irreplaceable value for growth, and who is best equipped to deliver it? That is her standard. Agencies that stand out are the ones that challenge the status quo, bring breakthrough ideas, and help translate those ideas into productive growth. The roles may evolve. The need for value does not. What Stood Out What stayed with me most
What Eric Gillin Learned by Following the Biggest Problem
Executive: Eric Gillin, Chief Brand Officer Company: Trusted Media Brands Industry: Community-driven entertainment across streaming, social, web, and print Company Snapshot: Trusted Media Brands is behind names like Reader’s Digest, Taste of Home, and Family Handyman, reaching hundreds of millions through streaming, social, web, and print. Format: CMO Journeys Interview Why It Matters Eric Gillin didn’t chase a straight line. He chased the biggest problem in the room—first in content, then in product, then in revenue. Now, as Chief Brand Officer at Trusted Media Brands, he’s connecting content, product, and distribution while pushing what he calls a “pivot back to brand.” For agencies, his viewpoint is useful because he’s worked in editorial, product, and ad sales—so he’s seen what actually moves work forward. And he’s allergic to shortcuts. Their Path, in Short Gillin breaks his career into three chapters. The first was as a writer and editor. He came out of college wanting to write, got pulled into the first dot-com wave, and went to TheStreet.com as a reporter. With no CMS, he learned HTML and “hand hack[ed] all the content.” He launched websites out of his living room, worked at Maxim, and later served as a digital director at Esquire and Hearst. In that chapter, he learned how to create, edit, and build the tools that help content work in a digital world. The second chapter was product. He went to Condé Nast and asked to work on product for Epicurious. That move blended his content instincts with product thinking and pushed him into a general manager mode—focused on how to run the machine behind the stories. The third chapter was sales. He moved into running sales for a group he’d been part of, then became head of U.S. ad sales at Condé Nast across brands and categories. He didn’t predict that path. But he says it fits his pattern: “I was always sort of going to where the biggest problem was.” Media kept changing, so he kept learning new languages. Big Themes From the Conversation Gillin’s engine is curiosity, but not the flashy kind. Early on, he watched friends get bylines and feel thrilled. He had bylines too, yet he realized he wasn’t “mega interested in being the center of attention.” What excited him was building: launching a site, hosting it, figuring out how systems work. “It felt good to build things,” he says—and that became the pull. He also carries a simple standard from his dad: “No one can take away the work.” Put in the time. Learn the craft. Gillin translates that into a warning against hacks: there are “no shortcuts.” The “cheat code” fades, so you have to come by the work honestly, start with the user, do something special, and then “insist on consistency.” That same steadiness shows up in his leadership style. He calls himself “jargon-free” and “drama-free,” and tells new teams, “I’m not a table flipper.” In a crisis, he leans on what he calls “service management”: “I work for my team. My team does not work for me.” If emotion creeps in, he takes a walk, takes a break, and returns to examine the problem clearly. And he’s blunt about uncertainty. Leading through the pandemic came with “no playbook.” AI brings the same feeling. In his words: “You just can’t depend on the past to get to the future.” Watch CMO Journyes Interview How They Choose the Right Agency Partners When I asked what cuts through when an agency or vendor reaches out, Gillin didn’t lead with credentials. He led with humanity. “Great ideas and brands cut through,” he says. Even with all the talk about measurement, he comes back to a simple belief: “We’re all human. And I think you know a good idea when you see it.” He also meets agencies where the pressure is real. He describes a world where “the math no longer mats out,” where “reach and frequency is broken down,” and where marketing decisions can shrink into spreadsheets. He doesn’t deny the math. He just doesn’t want it to be the whole conversation. So instead of starting with a CPM or KPI, he prefers to start with the audience. “Let’s talk about who you’re trying to reach,” he says, and how you want to reach them—through emotional connection, not just optimization. Otherwise, he warns, you may “get anything other than a spreadsheet back” that you feel good about buying, without changing anything meaningful. He’s quick to spot copy-and-paste thinking, too. He says he often slows work down with questions like, “Why are we doing this? Why are we doing it this way?” Sometimes it’s not a hard no—more like a “speed bump in the parking lot.” But the point is to challenge the comfort of “we always did it this way,” because “what worked yesterday won’t work today.” And if you listen closely, there’s a consistent thread in what he respects: honest work, clear thinking, and ideas that don’t depend on a temporary trick. He’s seen trends come and go. So the agencies that stand out aren’t the loudest. They’re the ones bringing a grounded idea that’s actually built for real people—and then showing they can deliver it with consistency. What Stood Out The most revealing moment wasn’t a framework. It was a cookie exchange. Gillin described a Taste of Home event in Cleveland that “sold out in six minutes.” Three hundred people showed up with cookies to swap, and he laughed at the sheer volume. Then he talked about a “peach cookie,” a Midwestern specialty he’d never seen—made to look like a peach and tasting “just like peaches.” He called it “mind-blowing.” It’s a small story, but it captures his whole approach. He’s chasing the human element: real people, real places, and moments that feel true. 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 NextBigWin Pro member.