Mike Bell’s Journey From Mission Thinking to Marketing Leadership
Executive: Mike Bell, Chief Marketing Officer Company: Everspring Industry: Higher Education Technology Company Snapshot: Everspring is a technology-first partner that helps universities drive enrollment and growth by connecting marketing, data, and platform infrastructure. Format: CMO Journeys Interview Why It Matters Mike Bell’s path to the CMO seat did not start with marketing. It started with airplanes. His journey moves from the Air Force to consulting, CPG, startups, digital marketing, and higher education. For agencies, his perspective is useful because he brings a rare mix of structure, humility, speed, and strategic calm to a market that keeps changing. Their Path, in Short If you asked Mike Bell in high school whether he would become a CMO, he would have said no. So would everyone else. From the time he could walk and talk, Bell was obsessed with planes. That obsession led him into the Air Force, where he worked in a structured, mission-driven environment. It was not marketing. But it shaped how he thinks. The Air Force taught him to step back, see the whole board, and move toward an objective even when the path is unclear. One lesson stuck with him: “The only wrong decision is indecision.” He did not fully understand it as a young officer. Now, he thinks about it every day. After the military, Bell moved into consulting on purpose. He wanted a role where he could wear a lot of hats. From there, he moved into CPG and had to learn how to be a marketer outright. Then came digital marketing, where the language shifted to cost per click, retargeting, conversion, and user experience. Higher education added another layer. Bell describes it as a humbling market because the pipeline does not move like e-commerce. There are fewer easy signals. Less instant feedback. More complexity. Across each chapter, the pattern is clear: Bell kept stepping into unfamiliar rooms, then learning how to make sense of them. Big Themes From the Conversation One theme in Bell’s story is comfort with discomfort. In the Air Force, he said, as soon as you got comfortable, they made you uncomfortable again. That was not always pleasant. But it helped him become a leader who does not panic when the ground shifts. Another theme is learning how leadership changes by environment. In the military, hierarchy is built in. In business, Bell had to develop different muscles. He had to learn to sit with a team, talk through the problem, and invite more perspectives into the room. He admits he underused some people early in his corporate career. That realization made him better. Mentorship also shaped him. Marvin Davis, his first CMO at LifeLock, taught him lessons he still carries, like putting the right players in the right positions and answering the question before it is asked. Colonel Alston, his first commander, showed him that leadership also means empathy, care, and going the extra mile for your people. Bell also has a calm relationship with risk. When you have worked in environments with real consequences, marketing decisions look different. They still matter. But perspective helps. For Bell, the goal is not to defend a process because it exists. The goal is to remember the original intent and ask whether there is a better way. Watch Or Listen CMO Journey Interview How They Choose the Right Agency Partners When I asked Bell how he thinks about internal teams versus outside partners, he started with strategy. Everspring has brought more organic and content strategy work in-house, especially where AI fluency matters. Bell said the team has turned away sharp people who were not far enough along on that front. But that does not make agencies less relevant. In his view, the right partner becomes more important when the landscape gets harder to read. What stands out to Bell is not a broad service menu. It is the ability to see patterns across platforms, brands, and industries. He wants partners who can help a team understand what is shifting, where to place bets, and how to look at the picture holistically. He is especially alert to whether agencies are taking AI seriously. Bell said he has been surprised to see some organic and SEO-oriented agencies still not fully engaging with it. That is a miss. He expects partners to bring useful perspective: reports worth reading, trends worth watching, and clear thinking on how the work is changing. That is the kind of thought leadership that gets his attention. Not vague claims. Not recycled takes. Useful, specific perspective that helps him see around corners. Bell also has a balanced view on specialist versus full-service agencies. If an agency is too specialized, it can miss the forest for the trees. If it tries to do too much, he worries about depth. The right fit sits in the middle: a partner that starts with the problem, the audience, and the message, then chooses the right tactics. That order matters. Strategy first. Tactics second. His view of AI is just as grounded. Bell calls it a “very brilliant intern.” It can help with briefs, blog content, and ad copy. But it has not replaced strategy. He sees it as a better co-pilot than aircraft commander. That is also his advice to agencies. Do not use AI as a substitute for real work. Use it as a force multiplier. Bell compares it to an e-bike: you can pedal hard and feel supercharged, or you can sit still and let the machine do the work. Only one version makes you better. What Stood Out What stood out most was how human Bell’s leadership philosophy is beneath the systems thinking. He talks about objectives, funnels, and decision-making, but the moments that shaped him came from people who invested in him. A commander saw potential. A CMO taught him how to think ahead. Colleagues helped him become a better leader. There is also something revealing in his reset routine. Bell likes going to the gym in the morning with his wife because,
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
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
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
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
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.
Josh Churnick’s Eclectic Path to Practical Marketing Leadership
Executive: Josh Churnick, Chief Marketing OfficerCompany: Vertex Service PartnersIndustry: Residential exterior home services (roofing-led, multi-brand platform)Company Snapshot: A platform of regional brands supported by shared servicesFormat: CMO Journeys Interview Why It Matters Josh Churnick didn’t take a straight line into the CMO seat. His path runs through very different worlds, and it shaped a leadership style that’s both creative and deeply practical. He talks about marketing as a craft you can measure—because the customer always tells you what’s working. And for agencies, his viewpoint is refreshingly direct: he’s clear on what earns trust, what breaks it, and what a real partnership actually requires. Their Path, in Short Josh describes his career as “eclectic” until he found the lane that fit. Early on, he wasn’t trying to become a “home services marketing guy.” He was trying to become a better marketer—period—by learning different categories and different ways customers make decisions. One of his earliest chapters forced him to learn the basics in a hands-on way. After high school, he built a digital platform for independent music artists. The idea was simple: give artists a place to create profiles, share show dates, and grow an audience. He partnered with Billboard magazine and worked around performance venues connected to that ecosystem. It wasn’t a neat corporate role with a neat job description. It was the messy kind of work where you learn what people care about because you have to earn attention. From there, he moved through a mix of industries—entertainment, consumer packaged goods, restaurant groups, and insurance—building a broader sense of what makes marketing click. Over time, he noticed he was drawn to roles where the feedback loop was clear. He liked being able to set up tracking, run a campaign, and see the results plainly—“in black and white”—instead of having performance judged by taste or office politics. That preference eventually led him into home services, where response can be direct and attribution can be tight if it’s set up correctly. For Josh, that environment made marketing feel honest. If something works, you see it. If it doesn’t, you see that too. And that’s where his voice as a leader sharpened: do the creative work, yes—but let reality decide. Big Themes From the Conversation Josh sees marketing as the bridge between what a company offers and what a customer needs. When marketing is great, it doesn’t just “look good.” It communicates value in a way a consumer understands and acts on. That’s why he keeps circling back to the balance of art and science. Creative matters. Messaging matters. But he doesn’t treat creative like a mystery that can’t be tested. He talks about trying things, comparing performance, and learning through outcomes. The goal isn’t to win an internal argument about what’s best. The goal is to find what customers respond to. A mentor’s advice helped lock in that mindset: don’t worry about what you like—worry about what works. Josh repeats that because it’s a trap he’s seen again and again. Teams fall in love with their own ideas. They chase the “cool factor.” And then they confuse their preferences with the customer’s reality. He also talks about personal growth in a way that feels honest. Earlier in his career, he admits he cared too much about how “cool” the brand seemed. Over time, that changed. Now he defines success by impact: if marketing helps the business run better, helps the teams downstream perform, and supports the people doing the work, then marketing is doing its job. Even when he touches on technology like AI, he frames it as exactly what it is: a tool. Useful, powerful, worth exploring—but not a replacement for judgment. In his view, marketing still needs people to guide it because marketing is still aimed at people. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked Josh what makes an agency relationship work, he didn’t start with awards or big names. He started with behavior—and he didn’t point the finger only at agencies. His philosophy is that agencies are extensions of a marketing team. That means partnership has to be real, not performative. And the first test of “real” is transparency. If an agency is expected to drive leads, then the client has to share what happens to those leads. Without that, the agency is flying blind. Josh’s clearest example is disposition data—what happens after the lead comes in. Did the lead convert? Did it not convert? What were the common reasons? If the client withholds that information, then optimization becomes guesswork. In his view, that’s a fast way to create frustration on both sides: the agency can’t improve what it can’t see, and the client can’t get better results from a partner it refuses to equip. He also has a sharp definition of credibility: outcomes. In home services, he says, attribution can be very clear when tracking is built correctly. That means performance can’t hide behind pretty reporting. Results show up—or they don’t. So when agencies talk about expertise, Josh listens, but he ultimately checks whether the work drives measurable impact. That’s why he’s cautious about “category claims.” Some agencies say they know home services, but when you look closer, their experience is thin or short-lived. Josh doesn’t say agencies can’t learn. He’s saying the learning curve can be expensive if the client becomes the training ground. At the same time, he doesn’t want partners who only know one world. Josh credits his own mixed background with giving him ideas he can apply in new places. He values a partner with range—someone who can bring in outside lessons without losing respect for the category’s realities. But range alone isn’t enough. He’s wary of agencies that feel “all over the place,” because they may not understand the mechanics that matter in a performance-heavy environment. The best partners, in his telling, combine real proof with real curiosity: they show they understand the category, and they show they’re still
How Sarah Cascone Leads With Clarity Under Pressure
Executive: Sarah Cascone, Chief Marketing OfficerCompany: Appriss RetailIndustry: Retail technology (returns, fraud, profit protection)Company Snapshot: Helps large retailers reduce fraud, manage returns, and protect profit across in-store and online channels.Format: CMO Journeys Interview Why It Matters Sarah Cascone didn’t plan on a marketing career—and that’s why her perspective feels grounded. She learned marketing through live rooms and real conversations, then carried those lessons into SaaS and enterprise retail tech. Now, as the first CMO at Appriss Retail, she’s clear about what earns trust and what wastes time—especially with agencies. Their Path, in Short Sarah grew up in Brooklyn and studied psychology in college. She once thought she’d become a criminal psychologist, but chose a different path because that work felt too depressing day to day. Instead, she poured herself into events and conferences. At Worldwide Business Research, she learned how to plan and execute a conference from the ground up—connecting messaging, experience, and audience. Then she moved into SaaS and joined Bluecore in its early days. Over time, she expanded her scope from events into PR, content, design, demand gen, and product marketing—until she was running the full marketing function. That shift was defining: marketing couldn’t be separate activities. It had to operate as one engine, embedded with sales and customer success, with shared goals and accountability. Now she’s applying those lessons at Appriss Retail in a more complex enterprise context. Big Themes From the Conversation Sarah has a simple belief about speed: “Speed forces clarity.” Under revenue pressure, she said, you don’t have time for confusion or “politeness theater.” Direct communication becomes an efficiency strategy—clear feedback, tough conversations, fast decisions. Her events background still shapes her filter for what works. Events taught her pattern recognition—what lands, what doesn’t, and why. But they also anchored her in something more basic: everyone is selling to a human being. Being memorable, real, and trustworthy isn’t extra. It’s the foundation. And she uses a blunt test: if your message doesn’t work in a live conversation, it won’t work in a campaign. She’s also decisive about “no.” She pushes back on brand-versus-demand debates because she sees them as a false binary. She says no to work that doesn’t move pipeline, accelerate it, or expand it—and she says no to shiny objects without a clear business case. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked Sarah what gets her attention from an agency, she didn’t talk about a portfolio. She talked about a point of view. She wants agencies to lead with perspective and evidence that they understand her business model. She said she gets too many pitches built for SMB or mid-market motions, even though she operates in enterprise. That tells her the agency didn’t do the work—and it signals a lack of respect for her time. That same respect-for-time lens shapes who should be approached first. Sarah’s view: It depends on the size of the problem and how tactical it is. If an agency is pitching something that clearly sits with someone else on her team, going straight to the CMO can feel misaligned. But if the problem is truly significant, then it makes sense to reach higher. Match your ask to the scale of impact. What separates great partners from the ones that struggle? Sarah said great agencies become an extension of her team—comfortable embedding not only with marketing, but with the broader org, and even working across leaders like the CRO and CPO. They understand strategy deeply, and the work reflects it. Most importantly, they reduce her cognitive load. They don’t create more decisions. They remove them. She described her marketing team as two pillars: product marketing, which tells the story in market (including content and thought leadership), and growth marketing, which distributes it (including outbound and events). And then there’s her favorite way to build credibility: executive conversation. Sarah described creating owned community moments for VPs and above—behind-closed-door strategy discussions that include customers and prospects, plus subject matter experts outside her company. The goal is to keep a real conversation going between major industry events, so the next step isn’t always “take a sales meeting.” It’s: add value without obligation, and earn the right to go deeper. She also chooses partners with intent. She works with a content agency, StoryArb, because they’re strong at editorial, subject-matter-expert-driven playbooks and newsletters—“the kind of content people actually want to read.” She also works with a retail-focused PR agency to extend the story through press releases, bylines, commentary, awards, and interviews. Agencies can learn from her community approach. Curated roundtables can build trust in a way cold outreach often can’t. That’s also why Next Big Win runs an Executive Access Program—executive roundtables designed to help agencies and partners build relationships with senior leaders through candid, small-group conversations. Learn more here. What Stood Out Sarah’s mix of intensity and self-awareness is striking. She talked about what it feels like to “shoulder an entire function,” and how that requires a personal operating rhythm that’s sustainable. She also named a hard unlearning: assuming she knows better than the person in front of her. That openness—paired with her speed—is a rare combination, and it says a lot about how she leads. 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.
Ethan Chernofsky and the Value of Staying Uncomfortable
Executive: Ethan Chernofsky, Chief Marketing Officer Company: Placer.ai Industry: Location analytics Company Snapshot: Placer.ai helps brands, retailers, real estate players, and investors understand what is happening in the physical world through location analytics. Format: CMO Journeys Interview Why It Matters Ethan Chernofsky did not build his career in a straight line. His path moved through agency work, public relations, strategy, and then into in-house leadership, where the stakes got bigger and the learning got sharper. That makes his story worth studying because it shows how a marketer can grow by chasing discomfort instead of avoiding it. It also makes his perspective useful for agencies. He has been on both sides of the table. He has pitched. He has been pitched. He knows what feels thoughtful, what feels forgettable, and what makes someone worth calling when the timing changes. Their Path, in Short Chernofsky describes himself as a regular kid from Pennsylvania. He played baseball, did well in school, and grew up with parents who made sure he stayed on track. But what stayed with him most was a fascination with people dynamics. He became interested in how people make decisions and what shapes behavior, which later became a core part of how he thought about marketing. He left home young, spent time in different places, and eventually built his career in Tel Aviv’s tech ecosystem. Once he got into that world, he says, one opportunity kept leading to another. He started on the agency side in public relations, working with companies including Wix, Lightrix, and Lemonade. That work gave him a rare vantage point. He got close to many companies at once and learned by watching how different leaders thought. He could see what strong storytelling looked like, what smart positioning sounded like, and how different businesses approached growth. But over time, he wanted something more. He did not just want to advise from the outside. He wanted to own the work more fully. The move in-house felt intimidating. He says that plainly. It was not just a new title. It was a new way of operating. Agency life had taught him pace and range. In-house life demanded depth, patience, and a willingness to listen. At Similarweb, he says, he had to learn from people who were already doing the work at a high level. Sometimes that meant talking less and absorbing more. That mindset stayed with him. Across each step, he seems to have been drawn less by comfort and more by the chance to stretch. He does not frame growth as a smooth climb. He frames it as entering rooms before you feel fully ready, then learning fast once you are inside. Big Themes From the Conversation One of the clearest themes in the conversation was his relationship with discomfort. Chernofsky says the fear never really goes away, and he does not think it should. To him, that tension is part of growth. If you feel completely settled all the time, you may not be pushing yourself enough. He had a striking take on imposter syndrome. He said he does not see it as a syndrome at all. He sees it as real. Every new challenge asks you to do something before you feel fully qualified to do it. In his mind, that is not a warning sign. It is the cost of getting better. Another theme was curiosity without ego. He says you can learn from everybody, both the people you admire and the people you do not naturally connect with. Some people teach by example. Others teach by showing you what not to do. Either way, he believes there is value in paying attention. He is also wary of simple labels. His view of the “full stack marketer” idea is direct: most people are not great at everything. They are strong in some areas, weaker in others, and always still learning. The important part is being honest about that. Know your strengths. Know your gaps. Keep moving anyway. Running through all of it is a sense of fascination. He talks about being energized by things he does not fully know yet. That may be one of the best clues to how he operates. He does not lead with certainty for the sake of appearances. He leads with curiosity, enthusiasm, and a willingness to test ideas in public. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked how he thinks about outside partners, his answer was balanced. His natural instinct leans internal. He likes having people close to the brand, living it every day. But he also sees the value of agencies when the match is right. The way he explains it is simple. Internal people bring depth. Agencies bring range. One person may know the business inside and out. An agency can bring multiple perspectives, more category exposure, and lessons from other companies and markets. So the question is not whether one model is better than the other. It is where the value shows up for the work that needs to be done. He used PR as a strong example. Placer.ai has worked with an external agency for years, and he pointed to the benefits clearly. The agency brings a broader market view and experience across multiple interests. But he also pushed back on the idea that bigger always means better. In that case, they did not want the largest shop. They wanted the right one. That idea shaped how he evaluates agencies more broadly. He thinks too many companies ask who did great work for someone else and treat that as enough. He believes the better question is whose model fits what you actually need. Sometimes that is a boutique agency. Sometimes it is a much bigger team. Size does not prove fit. Alignment does. He was just as clear about what gets his attention. Multi-channel outreach can work, he said, but only if the message is strong. Generic outreach does not land. Volume